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Dating Up
By J. Courtney Sullivan

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 Dating Up

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Dating Up
By J. Courtney Sullivan
ISBN: 0446697605
Genre: Inspirational & Self-Help

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Chapter Excerpt from: Dating Up , by J. Courtney Sullivan


Getting Ready

“Genius is of small use to a woman who does not know how to do her hair.”

—Edith Wharton

To get a date with the average man, all you need is a miniskirt, two breasts, and the willpower to ignore his calls for at least a week after giving him your number. But starting a relationship with a quality wealthy man is another matter.

The rich, as they say, are different. To them, summer is a verb, share is a noun, and rent is a passé Broadway musical. Men who are both rich and interesting want to know that the women in their lives can keep up. The good news for you is, you can probably already do that. But there are still adjustments that every one of us can make to look better, become more cultured, and sound informed.

Other dating books tend to advise us in one of two ways when it comes to working on ourselves. These books want us either to change completely and act like little man-pleasing robots (I won’t even get into how ridiculous that is), or they tell us, “You’re the best! If he doesn’t want to be with you, he’s nuts.”

That statement is comforting and all, but it always makes me wonder to whom the writer is talking: Who is the best? Me personally? Does the boring girl in my office have a copy that says “You’re, umm, boring. If he doesn’t want to be with you, I can sort of understand”? We can’t all be the best in every way. But if we want the greatest guys the world has to offer, we need to bring something to the table. The first part of finding Mr. Right is being ready when he appears, and a man of quality needs a woman who can keep up—someone who will look the part and act the part, too. This chapter offers an overview of the most essential topics that appeal to someone who is both cultured (such as art and wine) and male (such as sports and dude movies). These are all areas that you should (and possibly do) know a bit about anyway. But there is always more to learn. The best sort of man is informed, inquisitive, and interested in knowing about a wide range of topics. And the best sort of woman is no different.

Drugstore Cowgirls

As your mother probably told you when you were going through that gawky adolescent stage, it’s what’s inside that counts. But it’s what’s outside that your future husband will notice first. So let’s begin there.

When I worked in the Condé Nast building in Times Square—an office space that has more beautiful women per square inch than some Midwestern states have, period—my stock among my male friends immediately went up. I suddenly knew women who worked at Allure, Vogue, Glamour, Self, Lucky—and every guy I knew wanted to be set up.

I love matchmaking, so this was no problem. The first pair I introduced was Jack and Ellen. Jack works as a banker on Wall Street, Ellen as a beauty editor. They decided to meet for dinner at Balthazar on a Thursday night. That afternoon, I e-mailed Jack to see how he was planning to prepare.

I’m going straight from work, he wrote back. Why? Am I supposed to change or something?

Meanwhile, Ellen searched in the fashion closet for some fabulous new thing to wear. When you work at a women’s magazine, you have access to all the designer clothes you could ever want, and if you spilled the contents of your desk drawers onto the floor, an entire Sephora franchise might very well fall out. So Ellen didn’t need to go home before the date, either. Instead, she applied her concealer, foundation, bronzer, eyeliner, mascara, and lip gloss right in her office. When she was done, she looked like Ellen—beautiful and perfectly put-together.

Jack called me after the date, and the first thing he said was, “She’s gorgeous. I love how she doesn’t wear any makeup. Women look so much better when they go the natural route.”

I was floored. But it happened again and again. I’d set up my wealthy male friends with editors, and the guys would always comment on how little makeup the women wore. Because, of course, like all men, they think they love low-maintenance girls.

Bless their ignorant hearts.

What these men don’t know (and let’s keep it that way) is that it took years of experimenting with different makeup shades and textures to make those beauty editors look so darn natural. Flawless makeup applications leave you looking like you’re not wearing any makeup at all. And, as I learned from working in magazines, you don’t always have to go with the most expensive products to achieve the perfect look.

In Manhattan, uptown girls often stroll down the makeup aisle of Duane Reade Drug. Why? Because women who can actually afford high-end cosmetics know that some things are worth the money, while others are interchangeable with their cheaper counterparts. Learn to know the difference, and don’t be swayed by fancy packaging.

Always read the ingredient list. For example, the main ingredients in a bottle of CVS-brand Balanced Care Conditioner (retail value: $3.00) are water, cetearyl alcohol, cetyl alcohol, and stearyl alcohol. The main ingredients in a bottle of Kerastase Oleo-Relax (retail value: $16.00) are water, cetearyl alcohol, glycerin, and cetyl esters.

Yup, that’s right. Pretty much the exact same ingredients. And do you know what all those alcohols and esters do to your hair?

Neither do I. I’m guessing they make it clean.

Cosmetics, shampoos, conditioners, exfoliators, and body creams are physical enhancers. You don’t need a license to operate them, and they don’t come with an owner’s manual, so it’s fine to go with the cheaper option when it’s presented to you.

Top Ten Products for Under Ten Bucks These tried-and-true cheapies are just as good (and in some cases, even better) than their department store doppelgangers. 1. Maybelline New York Great Lash Mascara ($5.29). A best-kept secret of beauty editors, this is the most long-lasting and impressive mascara out there, period. Buy it in Blackest Black for lashes that just won’t quit. 2. Cover Girl Trublend Makeup Foundation ($5.79). The foundation you wore in high school is still one of the finest. And, as in high school, it won’t cost you your entire allowance. Feel free to buy the newest issue of Tiger Beat with the leftover cash. 3. Cover Girl Invisible Concealer ($5.79). A few dabs of this stuff, and blemishes and under-eye circles vanish. When people tell you that you look refreshed and ask where you’ve been, say Waikiki, not Walgreens. 4. Maybelline Expert Eyes Twin Brow and Eye Pencil ($2.99). Products that multitask are the answer to a working girl’s prayers. Products that multitask, make you look fabulous, and cost under three bucks are worthy of worship. Bow down. 5. Cetaphil Gentle Skin Cleanser ($7.39). Backstage at fashion shows, this stuff is flowing like Evian. It cleanses skin gently and thoroughly, and can be applied to a wet or dry face. 6. Lush Buffy the Backside Slayer Body Butter ($8.15). A friend in London introduced me to this skin-sloughing miracle. Seriously, it’s worth crossing the Atlantic for. But luckily you won’t have to, because Lush stores are popping up in cities all over the United States, and you can buy online at 7. Eucerin Dry Skin Therapy Calming Cream ($7.99). Sort of like the little black dress of moisturizers, this unscented cream is subtle and soft, and it will make men want to touch your legs. Need I say more? 8. Neutrogena Triple Moisture Daily Deep Conditioner ($6.00). This lives beside Kerastase and Garren on my shower’s conditioner shelf (another bonus of working in magazines is that you never have to buy your own beauty products again. Otherwise, I’d probably be riding the Suave train), and of them all it’s my absolute favorite. Leave it on for three minutes and rinse. Hair is TV-commercial shiny and soft. Go ahead, give it a swing. 9. Clean and Clear Absorbing Sheets ($5.49 for 50). Some companies charge such a fortune for papers that get rid of those gross little oily spots, you’d think you were going to frame them afterward. These sheets leave skin matte for hours, but aren’t overly powdery (or expensive). 10. Smith’s Rosebud Salve ($5.00). Romance can be tempestuous, but lip balm—like shoes and bags—loves you unconditionally. This one leaves your lips soft, shiny, and lightly scented (also comes in strawberry), and you can use it on dry hands, too.

Foolproof Tips for Applying Your Makeup Before a Big Date 1. Always begin by washing your face with a mild exfoliator like St. Ives Apricot Scrub, and follow with a lightweight moisturizer. 2. If your skin is relatively clear, use a tinted moisturizer to even out the tone instead of foundation—it provides lighter coverage for a more natural look. If you have blemishes in certain areas but not others, try dabbing a maximum-coverage foundation on them as concealer, then combine a bit of the same foundation with a lightweight moisturizer and apply the mixture all over. This works better (and is a lot cheaper) than using a separate concealer and foundation, because the colors are a perfect match. 3. Curl your eyelashes twice (for thirty seconds each time) with a heated eyelash curler (put it under your blow dryer for a few seconds but make sure not to burn yourself. Ouch!) before applying mascara. Some of the best mascaras are the ones from companies like Boujoirs, with white mascara on one end and black on the other. Apply the white first as a primer, then do two coats of black. This will make lashes appear fuller and hold the color longer. 4. Straight-up pink blushes are on the decline, as are orangey bronzers that leave you looking like an Oompa-Loompa. The best bet for any skin tone is a product that combines bronzing powder and a hint of pink, such as Cargo’s Miami Beach, or the famous Orgasm blush from Nars. Gel bronzers like Clinique’s True Bronze bronzing gel give skin a nice, translucent effect, but you have to be fast if you don’t want to look like a streaky mess, since they dry in about ten seconds. If you want to apply bronzer all over, not just on your face, bear this in mind: a makeup artist at a cover shoot once told me that Make Up For Ever bronzer was used on the set of Baywatch, because it’s waterproof, lasts all day, and doesn’t rub off on fabric. 5. Before applying lipstick, cover your lips with a thin layer of foundation and let it dry for thirty seconds—that way you get the exact shade that you see in the tube, rather than a mixture of the shade and your own lip color. The foundation also helps to set your lipstick, so it lasts hours longer than it otherwise would.

While the drugstore is fabulous for buying colors to experiment with, you should splurge on a few makeup essentials. I use Chanel’s tinted moisturizer—it smells faintly of roses—which gets tucked into my purse next to Neutrogena pressed powder and Chap Stick. It’s nice to have one or two special products. They give you a little confidence boost. But repeat after me: when purchasing expensive, department-store beauty products, always try before you buy. It’s important to see what your makeup will look like in outdoor light, how it settles after a couple of hours, and how your skin reacts to it the next day. Resist the temptation to buy cosmetics right after you put them on—they’re not going anywhere and even the pushiest salesperson won’t hold it against you if you use the old “I’m going to have to think about it” line. (Just be sure to get her name so that she’ll receive the commission when you come back.) Once you know what you like, you won’t have to do the repeat performance thing again. Plus, going back to the counter means you’ll get to snag twice as many free samples (companies like Kiehl’s and Prescriptives are especially great for this).

The try-before-you-buy mentality is doubly important when deciding on a perfume. A scent needs at least an hour to settle into your skin and mix with your natural oils before you can tell how it will smell for the rest of the day. At the perfume counter, tell the salesperson what you like in general terms (spicy, floral, fruity, etc.) and dab different formulas inside your elbows, on your wrists, behind your knees, and on your neck (don’t rub it in because that crushes the molecules and breaks down the scent). Again, ask for samples.

Leave It to the Pros

There are some beauty decisions that every girl must make for herself. One of these is determining which treatments she can do at home and which ones she’ll need to consult a professional on (and dole out her hard-earned cash for). A good rule of thumb is that waxing and hair cutting are best left to the pros (remembering how my bangs looked when my mom cut them in fourth grade always makes me more than happy to hand over my Visa card to the receptionist at Vidal Sassoon). Many women I know spend tons of money on manicures and pedicures every month, and wouldn’t have it any other way. Personally, I think it’s just as effective and relaxing to flop down on the couch with a glass of Pinot Grigio and a bottle of OPI’s Pinking of You. But that’s just me.

Hair color is also up to you. I probably wouldn’t attempt it myself at home (not since the Manic Panic massacre of 1993), but I know lots of beauty editors who do. Some at-home brands aren’t too bad—Goldwell and L’Oreal actually include moisturizing ingredients and add tons of shine to your hair.

When you do decide to go pro, there are plenty of ways to do it on the cheap. Places that are just opening will have good deals, so keep an eye out. Most salons provide discounts if you refer a friend or are a new customer. Many hair salons and spas (including Aveda, Bumble and Bumble, Frederic Fekkai, and Vidal Sassoon) have training schools for student stylists, where you can get a cut, color, or waxing at a reduced rate. You’ll have to wait a little longer, though (and, in the case of hair, each salon has its own rules—some require you to get a drastic cut, others make you sit and wait for hours while teachers survey their students’ work). At salons and spas without training facilities, always get the name of the best person on staff and ask if her assistants do treatments. Having been trained by the best, and still eager to please, they’ll do the same work for next to nothing.

Clothes Encounters

Speaking of getting something for next to nothing, I want to let you in on a little secret. The majority of twenty-something magazine editors in Manhattan (including me, back in the day) make about as much money now as they did from their afternoon babysitting jobs in high school. Yet these women dress like they’ve just walked off a runway. How do they afford it? You might say necessity is the mother of invention, if by necessity you mean Prada bags and Chanel sweater sets. It’s easy to live a life of high fashion on a budget—the sort of life that attracts interesting rich men (and makes the aforementioned budget a thing of the past).

Most men can’t tell the difference between a black pencil skirt from Gucci and a black pencil skirt from the Gap. Those who can are probably a little too high-maintenance (read: gay) for your purposes anyway. As with beauty products, do not be afraid to mix high- and low-end clothes. It’s worth making an investment in a few quality staple pieces, then supplementing with fun things from H&M.

The ten essential pieces that no girl should be without are as follows. Be willing to get them through whatever means necessary (gaining credit card debt, working a second job, signing over your firstborn child, etc.). These are the items that will see you through any date—be it dinner and dancing, or bowling and beers:

1. A little black dress. For two years I had a black halter dress from Banana Republic that never failed to lure the boys. That thing was like catnip for the Ivy League set, and it cost me only fifty bucks. Note: no matter how great you look in it, and no matter which man will be there, you can’t wear your LBD to an afternoon barbeque, dentist appointment, child’s birthday party, or car wash (or so my friends tell me . . .). As with tequila, admit that it’s good, but know your limit.

2. A pretty cotton dress or skirt. If you can’t wear your LBD for a trip to the park, what can you wear? This is your answer. You’ll look pretty, but not too formal; sexy, but not too provocative. Avoid a top that goes straight across if you’re busty—instead, aim for a halter or scoop neck. And no matter what your legs look like, make sure the dress covers your knees. Pair it with strappy sandals (don’t even think of wearing flip-flops).

3. The perfect jeans. The dressing room lines in the denim departments at Barneys and Bloomingdale’s are a testament to the popularity of designer labels, but I think the Gap still gives them a run for their money if you’re willing to sort through some not-so-flattering styles (read: straight-legged) to get to the good stuff. Aim for a pair that is low-waisted and slightly flared at the bottom. Darker versions are more forgiving and flattering for curvy figures, but may fade quickly. To reduce fading, always wash your jeans inside out in cold water. And throw them in the dryer for the ultimate stomach suction.

4. Black pants. I personally can’t get enough of the Editor pants at Express—you want black pants that are a bit stretchy and flared but not too tight; better to go up a size than to show your panty line to the world. Pair with sandals or sexy pumps.

5. One pair of three-inch black pumps. These babies can take you anywhere (even if you do have to take a cab three blocks to get there in them). Perfect for work, parties, or shopping (if your feet can handle it), or basically any day when you want to make your legs look longer and thinner. Just be sure to avoid subway grates and replace the soles once they start to get worn—usually every three months or so if you wear them often.

6. One pair of stylish sneakers. Please don’t ever be that girl who wears stilettos to a Yankees game. In your arsenal of date clothes, you should have at least one pair of stylish sneakers (they exist, I swear). Think Puma rather than Nike.

7. A trench coat. If you’ve ever watched Audrey Hepburn run through the rain in the final scene of Breakfast at Tiffany’s, I don’t need to tell you why this one’s a must. A classic coat in black or camel is best.

8. Jackie O sunglasses. Slide a pair on all year round to add an effortless hint of style and sophistication to any outfit. But don’t wear them indoors unless you are:

a. Anna Wintour

b. Extremely hungover

c. Recently back from a boxing ring.

9. A great bathing suit. You never know when a new man will fly you off to Bermuda, and frankly my dear, your Speedo isn’t going to cut it on a romantic weekend getaway. If you have a slammin’ body, by all means, wear a string bikini. For the other 99 percent of us, bear these tips in mind: for a boyish figure, go for bold patterns that will accentuate your slight curves, and try a two-piece with shorts on the bottom instead of a skimpy traditional cut; if you have big breasts, diagonal stripes can make them appear smaller, and a band right underneath can give the illusion of lift; if your hips are wide, try a two-piece with a skirted bottom.

10. Sexy lingerie. A good rule of thumb for the first several dates with a new guy is to wear your rattiest, holiest granny panties under your adorable outfit. This way, if you’re tempted to go home with him before it’s a good idea, you will hopefully be too mortified by the prospect of him seeing your underwear to actually go through with it. But once you are ready, hit Victoria’s Secret and try to look away from the cash register when they ring you up. Aim for sexy but sophisticated styles that make you feel hot (this is the most important part). If you’re comfortable in a lace thong, go for it, but if girly satin panties are more your speed, don’t worry—your man will be happy either way.

Cut-Rate Couture

There are two ways to find discounted couture clothing.

The first is sample sales: go early, since most of the good stuff gets snapped up fast, and don’t expect a dressing room. You’ll most likely have to change in front of everyone, so if you’re feeling modest, wear a bathing suit or tight yoga pants under your clothes. A list of upcoming sample sales in your city can be found at

The second way to get a closet full of couture is thrift store shopping. Pound the pavement, or try these Web sites:

With both makeup and clothes, once you have a sense of what you like, you can buy duplicates at a reduced price online. For discounted duds, try:

Time Is Money

Now that we’ve ensured that you’ll look great, it’s time to think about what you’ll say and do when your future husband approaches. Generally speaking, “I’ve just bought a whole bunch of makeup and clothes in the hopes of meeting a great guy, and doggone, it worked!” does not make a very successful opening line. To find the sort of man you want, you have to broaden your horizons, and familiarize yourself with a range of topics, including travel, art, film, literature, politics, food, and wine. From the very first time you speak to him, you’ll want to make it clear that you are confident, intelligent, and worldly enough to hold your own with any crowd. Knowledge of these things will help you do just that. And they might help you land a great job or business deal in addition to a new boyfriend.

Travel on the Cheap

The most interesting men are almost always well traveled, and they will expect their future wives to be, too (sorry, but your eighth-grade class trip to Niagara Falls doesn’t count). The good news is that these days virtually everyone has studied abroad for at least a semester, so you probably have some experience under your belt. The bad news is that these days virtually everyone has studied abroad for at least a semester, so you probably won’t dazzle him with your tales of swigging Bud Light at the Texas Embassy in London for three months with a bunch of kids from the University of Michigan.

Fear not. It’s possible to see the world on a budget. Travel is truly one of the best investments you can make. Just think: skip one dinner out, one trip to Zara, and two nights at the bar, and you can probably buy yourself a ticket to Greece. I traveled all around Europe for a year, and now that I live in New York I find that that experience gives me something to talk about with anyone—be it the time I went to Mardi Gras in a small village in Belgium, the month I spent hiking in the wine country in France, or the night I put my embarrassing childhood Irish step dancing classes to good use in a Galway pub, my travels have provided me with stories to tell for a lifetime.

One last added bonus of travel: it teaches you to exist outside of your comfort zone, which will probably come in handy when your wealthy boyfriend takes you home to meet his parents in their twenty-four-room mansion.

Getting there. Most airlines send out a weekly e-mail to customers highlighting the best new discounts available (register on their Web sites). American Airlines has a particularly good plan called Net SAAvers (, which lets you search for discounted flights to destinations all over the world. If you don’t feel like having your inbox full of reduced-rate flight alerts, log on to and register for the weekly Top 20 e-mail—it’s basically a roundup of the cheapest flights being offered on any airline.

My super-thrifty friend Aliya taught me this trick—go to to find the most affordable flight to your chosen destination, and then buy it directly through the airline. That way you avoid paying extra fees and you can change your flight without being hit by huge cancellation charges. Once you arrive overseas, it’s even cheaper to fly from place to place. Two discount airlines—Ryanair and easyJet—offer unbelievable rates within Europe. I once flew from London to Brussels for a pound on Ryanair! If you’re traveling within Europe, it’s also a good idea to invest in a Eurail pass ( This will let you do an unlimited amount of traveling between countries for only a few hundred dollars.

Choosing hotels. Book hotel rooms as far ahead of time as possible, and keep your eye out for any special offers. A one- or two-star hotel in the center of the city is fine if you can’t afford something nicer—you probably won’t be spending much time there anyway. Just make sure that it’s clean and safe.

Dining out. When traveling abroad, you’ll obviously want to sample the local food. But in order to stretch your money, try to eat only one major meal a day. When I was traveling with friends in Italy and France, we’d grab bread and cheese at a local market for lunch and then have extravagant dinners in lovely little cafés. When you’re busy sightseeing, who wants to stop that often to eat anyway? Do your wallet and your waistline a favor and keep meals in restaurants to a minimum.

Shopping. Resist the urge to buy the first fabulous jacket you see at a thrift store in Barcelona, or the first fifty-Euro box of chocolates you lay eyes on in Brussels. Instead, wait until the last day of your trip—if you still want that coveted possession after seeing what else is out there, then by all means buy it. But remember: shopping is like dating. Don’t be tempted to settle for the first seemingly great thing you see. There may be something even better right around the corner.

Sightseeing. In every major city in the world, it’s possible to spend a small fortune on sightseeing alone. But tourist attractions that cost a lot of money tend to be the most gimmicky and the least interesting. If you want to get to know a place and have an adventure there, walk, visit museums, do free things, hang out where the locals go, and ask a cab driver to show you points of interest instead of climbing on board a bright red tour bus.

Changing money. Change money at your local bank ahead of time to save on service fees. If you need to change more money once you arrive overseas, it’s best to do it at an ATM, and take out all you’ll need at once rather than going back again and again, since both the foreign bank and your bank at home will charge you a small fee for processing.

Speaking the language. Americans have an embarrassing tendency to think that speaking English loudly is the equivalent of learning a foreign language. When traveling abroad, familiarize yourself with basic phrases such as yes, no, please, thank you, Can you tell me how to get to? How much does it cost? and (if you must) Do you speak English?

Staying safe. It’s a big, exciting world out there. And it’s also a little bit scary sometimes. When traveling alone or with female friends, familiarize yourself with your surroundings. Make sure you know how to get in touch with the police and the nearest American embassy. Don’t travel with valuables, and store your passport and credit cards in a hotel safe. It’s also a good idea to keep a photocopy of your passport with you (and leave another copy at home with someone trustworthy). That way, if yours gets lost or stolen, you can easily prove who you are to the State Department and expedite the issuing of a new one.

Splurging. Why is it important to save your pennies while traveling? So you can treat yourself to something luxurious at the end of your trip, of course! Stay one night in a great hotel or eat at least one meal somewhere insanely expensive and drink at the bar afterward—you could meet a very rich man, so think of it as an investment in the future (one that’s a hell of a lot more fun than your Roth IRA). During college, my friend Sandra went to the south of France alone for three weeks and stayed in youth hostels. But the night before she was due to fly back home to Boston, she checked into a fabulous spa and resort. It was there, in the massage prep room, that she met a businessman with a house in Bordeaux. Needless to say, Sandra missed her flight home. She stayed in France for another month and she didn’t swipe her credit card once.


An all-expenses-paid trip to the south of France is a great way to learn about many topics: good food, romance, Edith Piaf, and above all, wine. Alas, not all of us are so lucky.

Let’s play a word association game. If I say “salt,” you think shaker. If I say “shopping,” you think bag. If I say “wine,” you think . . . if the word cooler popped into your head, you’ve got a lot of work to do.

Cultured men are impressed by a woman who knows how to order wine. When he asks you what you’d like to drink at dinner, an answer like “Oh whatever—something white” is fine, but it’s not exactly going to knock his socks off. Remember that from the moment you meet him, your man is sizing you up to see if you’re marriage material—the same thing you’re doing to him. Not that anyone ever got the three-carat Harry Winston just because she knew her Bordeaux from her Burgundy, but every little bit helps.

The first thing to do is find a wine shop in your area. Get to know the people who work there, and ask them for advice and lots of samples (hey, it’s for research). Many shops have weekly tastings, where you can try new wines and learn about their origins. Some even offer classes, which can be informative, since the best way to understand wine is simply to drink it. Not to mention, the caliber of man who attends these events is pretty darn high. Once you know what you like, you can often get it at a reduced price if you buy by the case. And some places will sell you mixed cases if you ask nicely.

Perhaps you prefer to learn about wine by drinking copious amounts of it at home. May I suggest This Web site is a valuable tool for learning about and buying wine, with detailed descriptions of wines from around the world, information on joining wine clubs, and the best sales and specials I’ve ever seen. Also, their staff is incredible. E-mail them any question, and they’ll get back to you right away.

If you already know a thing or two about wine and want to learn more, the University of California at Davis offers a distance course. Check out their Web site at www.wineserver But if you’re not planning to become a sommelier anytime soon and just want a cheat sheet, here are the most common wines, broken up into bubblies, reds, and whites.


Hopefully your union with a smart, financially secure man will lead to fewer nights sipping seltzer on the couch, and more nights on the town drinking a far superior bubbly beverage: Champagne. The only true Champagnes are those made in the Champagne region of Northern France from a blend of Chardonnay, Pinot Noir, and Pinot Meunier grapes. Champagnes labeled Brut Absolut, Brut, and Extra-Dry will have a dry, refreshing taste, while those labeled Sec, Demi-Sec, and Doux are sweeter. Champagne is not like beauty products—here, the price tag matters. The more expensive, the better it will taste, and cheap Champagnes are pretty ghastly.

For bubbly on a budget, try a sparkling wine instead (these are basically the same, but cannot be called Champagne because they weren’t grown in that region). The best of them use the same laborious method that is used to create Champagne. One particularly good (and cheap) sparkling wine is Cava, a fruity, delicious version grown in Spain.

Serving bubbly. When serving bubbly at home, make sure that it is well chilled (it should sit in the fridge overnight, if possible). Unlike other wines, once you open it, bubbly can’t be recorked, so you won’t be able to put it back in the fridge between rounds. Keep an ice bucket on hand, and store your bubbly there to keep it cool all night (or for the half hour it takes you to down the bottle).

Red Wines

•  Cabernet Sauvignon. The primary flavors of Cabernet are heavy, dark fruits like black currant and blackberry. Interesting versions, like interesting men, hail from all over the world—Italy, Spain, Australia, Chile, Argentina, and California. The best Cabernets are medium- to full-bodied and very dark in color. Often blended with other wines to detract from its heaviness, straight-up Cabernet isn’t meant for sipping on its own—definitely serve with a hearty food that can keep up.

•  Chianti. Chianti hails from the region of the same name in Tuscany. (If you like the wine, why not invest in a country home? It will save on shipping.) It is made from a blend of grapes: the most pronounced is Sangiovese, but it may also contain Cabernet Sauvignon and others. The best Chiantis have a slight floral taste, and should be served with (what else?) pastas and Italian dishes with red sauce, such as chicken Parmesan.

•  Merlot. Merlots are generally full-bodied and dark in color, but they are less heavy than Cabernets. Because of this, they can be sipped on their own and still hold up when served with food (best with warm, home-cooked suburban sort of meals like roast beef or chicken—also great with takeout pizza). Merlot is full of fruity flavors—particularly cherry and plum. It gets blended with Cabernet Sauvignon to make almost all Bordeaux reds. Some cheap wines can be delicious, but Merlot ain’t one of them. If you’re in the mood for it, splurge. Some of the best Merlots are made in California. Other good versions come from Oregon, France, Italy, and New Zealand.

•  Pinot Noir. You may remember me from Sideways. Pinot Noir is like the ultimate dating fantasy (the one we’re not indulging anymore). Winemakers who produce it like a challenge. They take the most difficult, fickle grapes, and painstakingly tend to them in the hopes that the perfect wine will be the outcome (tell me you never tried this on one of your difficult, fickle exes). In some cases (particularly in Oregon, California, and France), it actually works, and the resulting wine is absolute heaven—soft, perfumed, fruity deliciousness (older Pinots tend to be more earthy). But Pinot Noir is one of the easiest wines to mess up, and rather yucky versions exist everywhere. As with Merlot, you’ll have to shell out some cash to get the best. Serve with fish or dark, rich poultry, like duck.

•  Syrah/Shiraz. Syrah is a spicy, show-stopping wine that has long been a central player in the Rhône region of France. More recently, it’s become enormously popular in Australia (where it is called Shiraz, and often blended with Cabernet Sauvignon). Some of the best comes out of Australia, and it’s easy to find a really good bottle for next to nothing. I always have a steady supply of Yellow Tail Shiraz (about seven dollars a bottle) on hand. It’s best with spicy stews or just on its own. Syrah is made in various styles and can range from soft- and medium-bodied with berry flavors to deeply colored, bold, and peppery. It has a distinct chocolate-y undertone that makes it the perfect after-dinner wine.

Serving reds. Most people think that red wine should be drunk at room temperature. In fact, the best temperature at which to enjoy its various flavors is at about sixty-five degrees Fahrenheit. Store red wine in a cool, dark place until ten minutes before serving. Then pop the whole bottle in the fridge to slightly lower its temperature. The resulting flavor will be more robust and full.

White Wines

•  Chardonnay. Chardonnay is well known among wine connoisseurs for being the grape used to make France’s beloved white Burgundies and Champagne. But here’s what the average wine drinker needs to know: Chardonnay is the Cabernet of whites. The most-often drunk white wine, Chardonnay can be rich and delicious, with hints of apple, honey, fig, and nuts. Some versions tend to be overly oak-y, because Chardonnay is stored in oak barrels (which help bring out its flavor if used correctly). Look for a label that says the wine is lightly oaked or unoaked, from California, Australia, or the south of France. Serve Chardonnay with creamy pastas or fish. Like Cabernet, it’s not very good on its own.

•  Pinot Gris/Grigio. If ever you go for drinks with a bunch of female magazine editors, and you are the first to order, ask for a glass of Pinot. I guarantee the entire table will follow your lead. Pinot Gris is a dark white wine that tends to be dry, crisp, and subtle—not unlike the Chanel suits worn by all those magazine editors. It’s originally from northeast Italy (where it is called Pinot Grigio), but has more recently been produced with lots of success in Oregon. Since it isn’t aged in oak, Pinot doesn’t have that wood-y taste that Chardonnay often gets. Instead, it has hints of peaches and nuts. Serve with a light food like grilled chicken or Caesar salad.

•  Riesling. Rieslings are very light and fruity, often tasting of apples, and sometimes extremely sweet. The best ones hail from Germany and Alsace, and make a great accompaniment to dessert, or to a light dish like white fish or sushi.

•  Sauvignon Blanc. One of the lightest and most affordable whites out there, Sauvignon Blanc can taste grassy (Bordeaux versions) or fruity, with hints of melon, berries, and asparagus (New Zealand). It ages well (you can keep it around forever—though if you’re anything like me, wine and cookies never make it anywhere near their expiration dates in your kitchen) and can be served on its own or with vegetable-based starters, like a tomato and mozzarella platter.

Serving whites. Like ice cream cake or revenge, white wines are best served cold—but not too cold. Refrigerate until twenty minutes before you plan to serve, and then remove the bottle from the fridge to allow a bit of the chill to drop off. This helps flavors peak and makes for a refreshing glass of wine.

Pairing Wine with Food

There are no hard and fast rules for pairing food and wine. In general, the color principle holds true (white with light foods, red with dark), but only because the lighter the food (in terms of richness, not color) the more it brings out the complementary flavors in a light wine. That said, as in love, opposites attract—a soft red can hold up against a hearty fish like salmon, and a full-bodied white can nicely balance out a heavy roast. Feel free to experiment with different varieties. White wine usually goes best with chicken, fish, entrée salads, creamy pastas, Indian curries, sushi, and Japanese or Thai cuisine. Red tends to go best with red meat, heavy stews, pastas with tomato sauce, and cheese.

A Recipe for Love

Knowing how to pair food and wine is a good skill to have while dining out, but it’s even more imperative when you’re eating at home. And guess what?—the next step in getting prepared to meet the man of your dreams is hitting the kitchen.

While I was doing research for this book, a close group of five female friends whom I know socially all got engaged to wealthy businessmen within a month of each other. Of course I had to ask them their secret. All of them are independent career women with varied interests and a lot to offer. But after a decade of fruitless dating in Manhattan, they had decided to take a traditional approach to courtship. No more paying on dates, no more refusing to let men hail them cabs or walk them home. They were going to find gentlemen in New York if it killed them. The funny thing was, as soon as they made this decision, all of them found guys who were more than willing to oblige.

A lot of men want to be gentlemanly, but they are petrified of making us feel disempowered. As one guy I interviewed put it, “I’m more than happy to pay on dates. But some girls are offended if you pay the check. Others just expect that you will. How am I supposed to tell the difference?”

Well, in the case of these five women, the difference was clear. They never opened their wallets, or even a door, while out on a date with their would-be husbands.

But, I asked them, didn’t they feel guilty? After years of going dutch and showing men that they were self-sufficient, didn’t it feel awkward to suddenly act like the little woman all the time?

No, they said. Because there was still equality, just not of the “you pay the check tonight, and I’ll get it next time” variety. Instead, the men always paid, and the women brought something else to the equation: domestic perfection. They’d invite their men over for home-cooked meals and take care of every detail. The table was set, the food perfectly timed, the wine chilled, the candles lit.

“When he walked in the door, I wanted him to feel instantly relaxed,” one of them told me. “And on those nights, he never had to do a thing. I wouldn’t let him wash so much as a dish, and I didn’t ever act flustered. Everything was taken care of—the food, the wine, the dessert. It’s not enough to serve filet mignon with a package of Twinkies afterward. It has to be a perfectly orchestrated event. And your apartment shouldn’t be a mess. No dishes in the sink, even if you have to wash them as you go while you’re cooking. Whenever my boyfriend came to dinner, it looked like I did that sort of thing every night. Which is a huge lie, of course. But he didn’t have to know that yet.”

All of these women have hectic careers, and refrigerators that contain more film and Veuve Clicquot than actual food. According to them, however, creating a night of domestic perfection is easy if you use the same skill set that you activate to get the job done at work: multitasking, emphasis on timing, and practice. Each of them worked hard to master three or four recipes, complete with side dishes and desserts. They then chose the perfect musical accompaniments, lighting, and table settings.

If this is making you want to retch, I understand. I’m certainly not advocating that you try to convince your new man that you’re something you’re not. And you clearly don’t have the time or inclination to be standing in the kitchen in an apron, ready to hand him his martini when he returns home from a busy day at the office. But what’s the harm in playing the perfect housewife every now and then? Yeah, it’s a throwback. But it works. And it will help to assuage some of your guilt when you let him pay the check each and every time you go out together.

Here are three easy sample dinners (all of them my mom’s creations, and all of them fantastic). Your man will appreciate the effort, even if he knows that you’re only pretending to be a happy homemaker. If you haven’t met him yet, practice on your friends. The best way to master the timing of a meal is to make it again and again, so by the time he shows up, you’ll be an old pro.

Italian Night

This is one of my mom’s most show-stopping dinners. An ex called me three weeks after I broke up with him to say, “I’m doing okay. But I miss your chicken, broccoli, and ziti.” It’s an over-the-top, calorie-laden meal that’s perfect for cold winter nights, and it’s delicious. But beware: do not serve to one of those body-conscious guys who weighs himself every morning unless you want to have him crying on your shoulder twelve hours after dinner is served.

Chicken Broccoli and Ziti

1 head broccoli

3 tablespoons of olive oil, plus 1 teaspoon for the boiling water

Dash of salt

2 or 3 boneless chicken breasts

1/2 cup (one stick) butter

5 ounces shredded Pecorino Romano cheese

5 ounces shredded Parmesan cheese

1 pint light cream

1 pound ziti

Chop broccoli. Set aside.

Place a large saucepan of water on high heat to boil (add the teaspoon of olive oil and a few dashes of salt).

Sautée the chicken breasts in the olive oil in a frying pan. Once it’s cooked, remove chicken from the pan. Set aside.

Melt the butter in a saucepan on very low heat, and gradually add the Romano cheese, the Parmesan cheese, and the light cream. Stir frequently and keep the heat as low as possible to avoid burning the sauce.

Once the water is boiling, drop the broccoli in and remove it as soon as it slides off a fork when speared (usually just a couple of minutes or so later). Add ziti to the same pot of boiling water, and cook as directed.

While the pasta cooks, cut the chicken into 1-inch chunks. Drain pasta, and place in a large serving bowl. Add chicken and broccoli, and pour the cream sauce over the top. Use serving spoons to toss.

Serve with: Garlic bread and a garden salad. For dessert, a fruit-based tart (you don’t have to make it from scratch, but hide the bakery box if you buy it) or vanilla gelato with mixed berries on top.

The wine: A light and fruity white will offset the heaviness of this dish. Try a Riesling, Pinot Grigio, or Chardonnay.

The music: An album that’s romantic, traditional, and mellow, like Dean Martin’s Italian Love Songs, or Frank Sinatra’s A Fine Romance.

Mexican Night

When my mom makes enchiladas or burritos, the food tastes so good and so authentic that we almost forget we are the whitest family on earth. This spicy, yummy meal works best on a Friday night in summertime. Serve on your front porch, if you have one (or, in the case of New Yorkers, on your fire escape).

Burritos with Chicken or Beef

Olive oil

2 onions

2 red peppers

2 green peppers

Boneless chicken breast or ground hamburger meat

Old El Paso seasoning mix

12-inch tortillas

1 can refried beans

2 tomatoes

8 ounces Monterey Jack cheese, shredded

Pour some olive oil into a frying pan, and heat it for a minute or two on medium heat. Add the onions and peppers (chopped), and once they’re browned, throw in the meat and cook on medium-high heat until no longer pink.

If you’re kitchen-savvy, there are many homemade spice combinations you can whip up, but if not, Old El Paso pre-made seasoning mixes do the trick, too. Add them as directed.

Place the buttered tortillas in a stack on top of the meat. Cover pan, and remove from heat. The steam from the cooked food will warm up the tortillas.

Once ready to serve, add refried beans, tomatoes, and cheese.

Serve with: Homemade or store-bought guacamole and tortilla chips. Guacamole is pretty easy to make, if you so desire: Combine 4 ripe avocados (cut into quarters, peeled, and pitted), 1 small red onion (diced), 1 clove of minced garlic, 1 tablespoon of lemon juice, 2 teaspoons of lime juice, and 1 jalapeño chile (optional) if you want to make it hot. Once ingredients are combined, cut up the avocado into small chunks, and add 1 medium tomato (chopped and seeded), before tossing and sprinkling on a dash of salt and pepper. For dessert, scoop up some raspberry sorbet, and make (or buy) a flourless chocolate cake. For a lighter option, you can whip up some Mexican hot chocolate—get Ibarra authentic Mexican chocolate (available in most specialty grocery stores). Heat whole milk in a saucepan over very low heat. Add two wedges of the chocolate for each cup of milk, and blend. Serve hot.

The wine: Forget straight-up red or white. For this meal, you need to make a pitcher of sangria. It’s easy to make in advance and store in your fridge, and it’s almost impossible to mess up. Combine 1 bottle of chilled red wine (Rioja, Cabernet, or Shiraz work best), 1/4 cup of brandy, 1/4 cup of triple sec, 2 tablespoons of sugar, 1 tablespoon of lime juice, a lemon and an orange, sliced thin. Refrigerate. Just before serving, add 1 cup of chilled seltzer and ice cubes.

The music: The Buena Vista Social Club soundtrack is perfect. Or anything by Silvio Rodriguez.

Roast Night

After some deliberation, my mom decided to allow me to print her gravy recipe. No matter what else you might learn from this book, her gravy recipe alone is worth the price of admission. Cooking a roast for a man might conjure up memories of Sunday-night dinners from his childhood—and plant the seed of a future with you.

Roast Beef with Vegetables

1 pound fresh green beans

1 (4-pound) sirloin steak roast

3 to 5 tablespoons self-rising flour

Salt and pepper, to taste

1 onion, peeled

1 jar onion juice

1/4 cup beef stock (optional)

1 can Dawn Fresh mushroom steak sauce

A sirloin steak roast is best—it’s very fatty, so it’s the most flavorful, and shrinks down a lot while cooking. Also, it’s harder to mess up than tenderloin or other lean cuts of beef.

Preheat the oven to 400 degrees Fahrenheit.

Set water to boil in a medium saucepan, and once boiling, add green beans. Cook 10 minutes. Meanwhile, remove all cellophane and paper from the roast (make sure you get that piece of cardboard or Styrofoam that’s affixed to the bottom). Place the meat in a metal roasting pan.

Put 1 tablespoon of the flour in the pan, and sprinkle another on top of the roast. Season with salt and pepper. Place the onion in the pan. Pop it in the oven and cook, 20 minutes to the pound. When the roast is cooked through, set it on a plate.

For the gravy: Remove excess grease from the roasting pan, loosen the thickened juices with a fork, throw in the remaining flour (just a tablespoon or 2), and a little bit of the green-bean water to make a paste. As desired, add more liquid—use juice from vegetables, juice from a jar of onions, beef stock, Dawn Fresh mushroom steak sauce (my mom’s secret ingredient). The key to flavorful gravy is to never use plain water, which dilutes the flavor rather than strengthens it.

Serve with: Mashed or roasted red potatoes and dinner rolls. For dessert, an apple, blueberry, or strawberry rhubarb pie with vanilla ice cream.

The wine: A rich Cabernet or Pinot Noir will complement the warm tones of this meal.

The music: Whatever most echoes your version of classic—be it Mozart, Ella Fitzgerald, or the Beatles.


That flawless dinner you cooked last night went off without a hitch. But now your man wants to take you out—to a museum, a play, a ballet, or an opera. Only trouble is, you don’t know your baroque from your Baryshnikov. These next two sections will help you navigate the art of appreciating the arts.


When I first took my little sister Caroline to Manhattan’s finest art museums—the Met, MoMA, the Frick—she had only one question: how did all those volunteer curators (mostly middle-aged women in silk pashminas and understated makeup) support themselves? I told her what I have always believed to be true: those curators don’t have to support themselves. They are the wives of extremely rich men.

A general knowledge of art is a must if you want to impress a cultured man. It shows him that you are worldly and smart, that you have an appreciation for beauty, and that you’ll be able to hold your own around his family. In fact, when you express interest in, say, cubism, he is very likely to respond with, “How funny—my mother is a volunteer curator at the Guggenheim. You two should meet.”

But what if, like me, you slept through one too many art history classes in college? What if the Met is just a beautiful building you pass on your way to Barneys? Fear not. Most museums have free nights every week, and it’s perfectly acceptable to jump into any tour group while you’re there. Listen carefully to what the curator says and ask questions about topics she mentions that interest you—Monet’s use of light, say, or her son who works on Wall Street.

When visiting a museum with your man:

•  Skip the informational headset. Those headsets that provide more detail than you’d ever need to know about an artist—from his use of color to his astrological sign to his childhood bed-wetting habit—may be interesting when you hit the museum with your grandmother. But when you’re on a date they can detract from the point: getting to know each other. (They’re also hazardous to your hair.) Instead, opt for a guided tour or (even better) buy the self-guided booklet so you can talk as you go.

•  Be aware of your surroundings. Good manners are always a must, but in a museum they are even more crucial than usual. Keep your conversation at a low volume, remember to turn off your cell phone, don’t stand too close to the artwork, and stay mindful of the pace of everyone around you. It’s okay to linger over a painting that you love, just make sure you’re not holding other people up.

•   Bypass the gift shop. Nothing says “I never go to art museums” like a thirty-minute visit to an overpriced gift shop that ends with you asking your man to carry four of your eight new posters to dinner. If you really can’t live without a Monet stationery set, go back the next weekend by yourself.

•  Bone up on the basics. You don’t have to be an expert, but it’s good to have at least a general understanding of what you’re looking at. If you plan on viewing a particular exhibit, you can check out the artist’s work online ahead of time. If you’re making a more general visit, here are the most common artistic periods, and the right names to drop:

Renaissance (1300s): Leonardo da Vinci, Michelangelo, Raphael

Baroque (early 1600s): Caravaggio, Rembrandt, Peter Paul Rubens, Diego Velázquez, Vermeer, Gianlorenzo Bernini

Impressionism (1867): Claude Monet, Pierre-Auguste Renoir, Camille Pissarro, Edgar Degas, Paul Cézanne, Edouard Manet, Mary Cassatt

Fauvism (1905): Henri Matisse, Albert Marquet, André Derain, Maurice de Vlaminck

Cubism (1907): Pablo Picasso, Marcel Duchamp, Georges Braque, Fernand Léger

Abstract Expressionism (1940s-1960s): Jackson Pollock, Mark Rothko, Franz Kline

Postmodernism (1960-present): Stephen McKenna, Carlo Maria Mariani, Peter Blake, David Hockney

Opera, Theater, and Ballet

Perhaps these are three words that you’ve never associated with the practice of dating straight men. But in the course of interviewing wealthy guys for this book, I ran into quite a few who said that a woman’s behavior at the opera, theater, or ballet speaks volumes about her breeding and manners. Here are the essentials for how to act.

Dress up. Modern etiquette does not dictate that you have to, but dress up anyway. If you are attending a matinee, wear a casual cotton skirt or dress. If you’re going to an evening performance, aim for something a bit more formal. Nowadays, depending on where you live, anything goes when you’re at a show. In London, lots of people wear jeans to the theater on Saturday night. But throwing on a skirt and heels shows that you care enough to make an effort.

Be punctual. There are always a few stragglers at any performance—those people lurking guiltily in the shadows until the end of Act I. Don’t be one of them. Make sure that you are at the theater, with tickets in hand, at least twenty minutes before the show starts. This means that if you are picking up tickets at the box office, you should be half an hour early. If by some chance you do arrive late, it’s up to the usher to decide when to allow you in. You might get to sneak to your seats after the overture, but you may have to wait even longer. Be polite and don’t argue with him. And next time, get there early.

Shut up. Once the lights go down in a theater, even the most refined adults sometimes start to act like kids at a boring school assembly. They shift in their seats, they unwrap cough drops, they flip through their programs, they whisper to their husbands, “Wasn’t he on CSI: Miami last week? No, no. Not him. The one playing Orlando.” It’s essential to be silent while watching a play, ballet, or opera. Make sure your phone is turned off, keep your hands in your lap, don’t get up to go to the bathroom, and don’t open your mouth until intermission. And when you see musicals, don’t ever sing along. I don’t care if Oklahoma! is your all-time favorite show and you know every word to “Surrey with the Fringe on Top.” You’re at the theater, not a Kelly Clarkson concert, so behave.

Applause. As they say before TV cop shows, viewer discretion is advised. There’s no need for you to be the loudest clapper in the auditorium—or the first. In general, applause occurs at the end of every act, and sometimes at the end of a major dance number, scene, or aria. During a classical music concert, it’s important not to clap until the piece is over. Clapping between movements is not allowed or expected. If you’re not sure whether to clap at any given moment, wait to see what everyone else does. Clapping is polite, and standing ovations at the show’s end (though far too commonly done these days) are fine. But never, ever scream or whistle to signify your enjoyment unless you are at a football game. If the spirit moves you at the opera, you can yell out “Bravo!” (for a male performer), “Brava!” (for a female), or “Bravi!” (for two or more performers).

Making an exit. Unless the theater is on fire, there is no excuse for leaving your seat until the house lights come up. That’s all there is to say about that.

Dude Movies for a Million, Alex

Wealth aside for a moment, here’s an important lesson to learn: contrary to what many women believe, men don’t find it endearing that you’ve never seen their favorite movies. One way to separate yourself from the pack is to start up a conversation about which of the Rocky flicks was the best or how you just can’t get enough of watching Kevin Costner play baseball. This worked well for a friend of mine when we went with a group of four English (and, incidentally, quite wealthy) guys to see Kill Bill. As we were walking out of the theater, I gave my standard “too much blood, too many women in spandex” comment. My friend, however, busted out a full review of all the Japanese directors Tarantino paid homage to, and the next day, I kid you not, three of those guys called to ask her out. The only one who didn’t was my boyfriend, and he probably would have done the same if he hadn’t been on a Meryl Streep-a-thon lockdown in our apartment. Hey, they should experience our movies, too.

So if you think Full Metal Jacket is just a strangely uncomfortable fashion choice, or you don’t know your Swingers from your Swing Kids, I’d suggest stocking up on the popcorn. Here’s a list of the dude movies you must see (feel free to alternate viewings with Meg Ryan flicks as necessary).

The Alien franchise

Anchorman and Old School

Apocalypse Now

The Big Lebowski and Fargo



Cool Hand Luke

Die Hard I-III


Donnie Darko

The Exorcist

Full Metal Jacket


Godfather I and II
(The third one is awful. He will appreciate your powers of discernment.)


The Great Escape


Major League

Monty Python and the Holy Grail
(or any Monty Python movie, for that matter)

Natural Born Killers

The Natural


Pulp Fiction

Raging Bull

Rebel Without a Cause

Rocky I-V


Saving Private Ryan



The Shawshank Redemption

The Shining



This Is Spinal Tap

Taxi Driver

Terminator I and II

Top Gun


The Usual Suspects

Take Me Out to the Ball Game

In much the same way that men—regardless of how wealthy they are—like it when you’ve seen their favorite films, they also appreciate a woman who knows at least a little bit about sports. When I interviewed guys on this topic, almost all of them said that they like going to games on dates, but can’t stand it when a woman asks tons of obvious questions about what the players are doing. Even worse are the women who go, but just act bored out of their minds the entire time. One lawyer friend of mine told me that he brought a girl from his office to a Mets game on their second date. “For the first few innings, she just talked to a friend on the phone,” he said. “Then she finally hung up, and I was relieved for about five seconds—until she pulled a little bottle from out of her purse and started painting her nails.”


Remember that sporting events, in addition to being a hobby and a pleasure for some men, are also the backdrop for a lot of business meetings (both yours and his). You don’t want your man picturing you giving yourself a manicure in his boss’s luxury box. If he does, you can consider the game over.

I don’t want to stereotype here, because I know plenty of women who love sports. But I, for one, do not. I didn’t even like Sporty Spice. I used to be the girl who went to the basketball game, cheered loudly, and then on the drive home asked, “So, who won?” Over the years, I have learned how to feign interest while watching sports (and sometimes I am actually interested . . .). Here’s the cheat sheet for those of you who are similarly clueless. But don’t worry if you can’t bring yourself to memorize (or even read) it. Just be enthusiastic, and try to have fun. (Remember: where there’s a sporting event, there is pizza and beer. Or at least cuddling on the couch while you watch ESPN.)

Basketball: The Basics

The National Basketball Association (NBA) is divided into two conferences, Eastern and Western. Each team has twelve players who rotate throughout the game—five players on the court at a time. Basketball season lasts from October through June, at which point the winning team in each conference competes in the NBA Finals. Just like your sorority scavenger hunts in college, the team with the most points wins. Teams face off for twelve-minute quarters (no, you won’t be out of the arena in less time than it takes to watch an episode of The Sopranos—because of time-outs, the average game lasts for about two and a half hours). Baskets (or field goals) are worth either two or three points, depending on whether they’re shot from behind or in front of the painted arcs at either end of the court (called the three-point line). Penalty free throws are worth one point each. Players must dribble (bounce the ball with one hand) while running, and—unlike in your sorority scavenger hunt—they are not allowed to hold, trip, hit, or push. If the game ends in a tie, overtime periods of five minutes each are played until one team scores the most points.

Basketball: The Guy

While other sports fans are known to worship their sport of choice with a clicker and a bag of Cheetos, the basketball fan tends to actually play as well as watch. Thus, he is your best bet if you’re looking for someone fit.

Pro basketball teams play several times a week, but they get a lot less television airtime than football or baseball games. Translation: you can feign interest in his favorite team without devoting several Saturdays a year to it.

Baseball: The Game

Major League Baseball teams are divided into two groups: the National League and the American League. At the end of every season (April through October) the pennant winners of each league compete in the World Series. Baseball is known as the great American pastime for good reason—you can pass some serious time watching a game, since there’s no limit to the length (though most are over in about two and a half hours). A game consists of nine innings (like basketball, if the game is tied at the end they keep playing), each one split into the top, when the visiting team is at bat and the home team is in the field, and the bottom, when they switch positions. Each batter gets three strikes before he’s out. The object of the game is to score as many runs (a run is a completion of all the bases) as possible. Batters hit either a single (running to first base), a double (running to second), a triple (running to third), or a home run (making it around all the bases and back to home plate). The opposing team mans the field and tries to tag the base runners out before they make it to home plate.

Baseball: The Guy

Baseball is often referred to as the thinking man’s sport, but all those extra IQ points might be wasted on an encyclopedic knowledge of statistics and scores. Each team in the Major Leagues plays an average of six games a week, so if he’s truly devoted, you may be spending a lot of nights on the couch—or getting him a TiVo for his birthday.

Football: The Game

Pro football can be a little intimidating if you didn’t grow up watching it every Sunday (ahem, thanks, Dad). The National Football League (NFL) is broken into two conferences: the American Football Conference and the National Football Conference. Football season begins in September and lasts until the beginning of the following year, at which point the winning teams from each conference compete in the Superbowl. A football game is broken into fifteen-minute quarters—but, as I learned as a little kid while fighting for the remote, it lasts a lot longer than an hour because of time-outs. Think three times as long.

There are two teams in a football game: offense and defense. The offense’s goal is to carry the football across the other team’s goal line (and into the end zone). The offense gets four downs (or chances) to advance the ball ten yards. If they don’t succeed, it’s the other team’s turn. The defensive team tries to stop this from happening by catching the ball mid-pass (called an interception) or by causing the offense to drop the ball (called a fumble). The team with the most points wins. If a game is tied at the end of the fourth quarter, teams play one fifteen-minute overtime (called “sudden death”). If it’s still tied after that, don’t worry: the game ends in a tie and you can start watching reruns of The Golden Girls.

Football: The Guy

The good news is that each team in pro football plays only one game a week. The bad news is that this gives the football guy six days to get pumped and talk endlessly about strategy (you will become intimately familiar with the term “Monday morning quarterback”). A real football fan is relentlessly faithful to his team, his friends, and (bonus!) the woman in his life.

Football, basketball, and baseball are the sports most often watched by the masses—both on TV and in person. But certain athletic activities hold even more appeal for wealthy, cultured men (namely the sports that they might have played in prep school, and at which fans are more likely to be covered in Polo than in body paint). You might want to consider brushing up on one or more of the following, because you may be called on to watch—or even play—them over the course of your relationship.

•  Golf

•  Tennis

•  Sailing

•  Skiing

•  Soccer

•  Squash

•  Lacrosse

SECRET WEAPON: Fantasy Sports

The following is a lesson in adaptation. And (sort of) in sportiness.

Recently I was out with several guys who were complaining that the women in their lives cannot begin to understand the importance of fantasy sports. When I mentioned that I am on an all-girls fantasy baseball team and that I fully understood when my boyfriend canceled dinner one Saturday night because his fantasy football draft had been going on for twelve hours and was nowhere near done, these guys looked at me like I was Angelina Jolie in a string bikini.

But, as I went on to explain to them, a year ago I would have thought fantasy sports were immature, stupid, and a waste of time. My good friend Caitlin (who is actually sporty) decided to start an all-girls fantasy baseball league, and I got dragged into it. For those of you who don’t know what fantasy sports are all about, here’s the rundown: You and a bunch of other people form a league and you draft the best players from different teams, forming a sort of superteam. You input all your players into a form on Yahoo! (go to http://fantasysports and the Internet does the rest. Each time one of your players scores in a real-life game, the results of his singular actions are tallied and put toward your team’s total results. If you’ve been living under a rock or in a cloistered convent for the last few years, here’s a piece of advice: men are insane about fantasy sports.

I am the consummate girly girl. I practically have the color pink radiating off of me. So when Caitlin announced that she was forming a fantasy league, I pretty much planned to phone it in and just pick a team of guys who all had the last name Smith. But then I was fully introduced to the wonderful world of fantasy sports online. You can view every player’s photo, stats, and ranking (incidentally, if you want to date a professional athlete, this is also a great place to check men out). I was hooked. Never in my life have I experienced something so close to my favorite childhood occupation—playing Barbies. When I was a kid, I had over a hundred Barbie dolls. When all the girls in the neighborhood would come over to play (there were about ten of us in all), we’d lay the Barbies out in rows, and take turns picking the ones we wanted. I was the master of this. Not only did I always get the best dolls, I devised ways of convincing the other girls that they wanted the crappier ones (mostly by talking them up, even though I myself had no interest in them). This was the exact strategy I used during my fantasy draft, and it worked.

In fantasy baseball, there are three categories that matter: speed, power, and average. If you’ve got Johnny Damon and Jose Reyes to cover you on speed, and then, say, Giambi and Piazza to score runs, you’re golden. For average, you need someone who has the total package, plus some extra, wild-card sort of qualities. In Barbies, there are likewise three categories: hot Barbies like Skipper and Malibu Barbie (speed), Barbies who actually do things, like lawyer or veterinarian Barbie (power), and Barbies who have extras, such as Heart Family Barbie, who’s otherwise quite lame, but comes with a four-door sedan and two babies (average). To get the perfect mix in a game of Barbies, you need some of each. Likewise with the fantasy baseball.

My fantasy team ranked in the top three all season long, even though I know nothing about sports. In part because of my Barbie-inspired drafting style, but in part because of my obsession with my players. I’ve realized that while women everywhere are killing time at work by e-mailing men and then obsessing about why it’s taking them more than thirty-seven minutes to reply, men are killing time by checking their stats on Yahoo! Apparently, the average guy does this ten to twenty times a day. And now, so do I. It’s just as addictive as overanalyzing relationships, and you can actually make money at it.

Most women look at fantasy sports as some alien occupation that only men or super-sporty chicks can get into. But in fact, they appeal to even the girliest of girls. Why am I going on about this? Because sometimes when we talk to men, it seems like we’re whispering at each other in two different languages from opposite sides of the Grand Canyon: You’re thirty years old, and you’re actually pouting over the results of a football game? You’ve got to be kidding me. But maybe we’re not so different. Maybe we just need a translator. If fantasy baseball is like playing Barbies and gossiping (which it totally is), then I’m a fan.

It’s important to stretch your boundaries and give him a little credit. If some guy had introduced me to fantasy baseball, you can bet I would have laughed it off as a stupid, puerile activity. But because it was my friend Caitlin, I actually gave it a chance, and fell in love. Keep an open mind about his interests. And in the meantime, get some girlfriends together and start a fantasy league. In addition to being fun, it will send any man you meet into an absolute tizzy. Here’s how to do it:

Pick a sport. The most popular fantasy sports are the most popular pro sports, and since they’re played based on actual games, the fantasy season coincides directly with the real season. Throughout the year, you can create leagues for football, baseball, basketball, and hockey, as well as more random sports like cricket and NASCAR. If you search hard enough, you can probably even throw together a fantasy mini-golf league. Extra points for knowing the circumference of the clown’s mouth and the relative speed of the windmill.

Generate interest. Your female friends might not be immediately sold on the idea, so do what Caitlin did to us—incorporate league rules that have nothing whatsoever to do with sports. In our league, every team had a theme song (or, in my case, every player had his own Frank Sinatra song), a general theme (like hot guys, fat guys, guys with facial hair . . .), and a hilarious name (wish I’d been the one to think up Sandy Cohen’s Eyebrows—and would love to see that printed on a jersey). Caitlin also threw a fabulous draft party, complete with a bucket full of pink cosmos.

Create the league and get everyone else to join. Go to Click on “Start a League,” and follow the directions for setting up teams and drafting players. Once you’ve drafted players in person, someone will have to enter everyone’s lineups online—or each individual can enter her own team to save time.

Do your research. There are many tools at your disposal. First and foremost: men. Ask the guys at work, in your social circle, and at bars and parties to help you out (even if you already know which players you want). I am the queen of striking up conversations with men, and I can tell you that this is the most successful method of doing so that I have ever used. Talking about fantasy sports puts men at ease, and separates you out from the dozens of other women asking, “So, where are you from? What do you do?” Yahoo! has a list of all available fantasy players, ranked in relation to the entire league and by position. And there are actually fantasy sports periodicals available at your local newsstand, or from the lending library of your latest crush.

Shamelessly use your newfound knowledge to meet men. When Caitlin started our fantasy league, she had no intention of using it as a tool for meeting men. However, she recognized even before I did that I would exploit it for that purpose faster than you can say “home run.” From the time you draft until after the Series, you have one fabulous pick-up line at your disposal. Last spring, my girlfriends rolled their eyes each time we went into a bar, and I propped myself next to the cutest guy with his eyes on the TV screen. “How’s Santana doing?” I’d ask. And when he smiled at me, I’d say, “He’s on my fantasy team.” Oh, who cares if it’s a little manipulative? It works.


If you can pull yourself away from your fantasy team for a few spare hours a week, here’s a suggestion that will benefit others and improve your chances of meeting Mr. Right simultaneously. Start volunteering. A lot of quality rich men were raised by mothers who did charity work. They also probably had to put in service hours in prep school. A lot of them never broke the habit. One of my best friends wanted a dog, but her fabulous rent-controlled building didn’t allow pets. She decided to walk shelter dogs instead and got a volunteer position through the ASPCA. On her second day of training, she met her now fiancé, a real estate attorney whose mother had been telling him for years about the organization’s great volunteer program (she’s on the board, naturally).

Need I say more?

Go to to find out what kind of volunteer work suits you best.

Required Reading

Once you meet that great guy on your weekly Habitat for Humanity shift, he’ll probably want to introduce you to his friends. A quality man’s partner needs to be able to discuss major works of literature as comfortably as she can discuss the most recent episode of The Office. Here’s a list of books that the educated class likes to refer to in casual conversation. In no way is this a comprehensive list (read Harold Bloom’s Canon if you want that). These titles range from obscure (and therefore important and impressive) to so damn obvious that PBS has made at least three miniseries out of them. Perhaps your Norton anthologies from college are still gathering dust under your bed in your parents’ house. Or perhaps you’ve spent more time with Cosmo than with Camus recently. Don’t worry. Here’s what to say if one of these classics comes up and you haven’t read it (or don’t remember it—hey, it’s been a while since freshman lit). In case of emergency, excuse yourself from the conversation, run into the other room, and check out

You’ll thank me later.

•  The Decameron by Giovanni Boccaccio. Like Dante’s Divine Comedy. But funny.

•  The Canterbury Tales by Geoffrey Chaucer. Farting jokes, cuckolded husbands, and bawdy women on horseback. Basically the Old School of the Middle Ages.

•  Paradise Lost by John Milton. In keeping with its Garden of Eden theme, the text commits a sin of its own by causing indescribable waves of boredom to wash over the reader.

•  Anything by Shakespeare. There’s a lot of ground to cover here, so I suggest familiarizing yourself with one comedy, one tragedy, and a couple of sonnets. That way when someone wants to discuss a Shakespearean play that you don’t know, you can just say “I vastly prefer [insert whichever one you know here].”

•  Anything by Jane Austen. Why? Because every cultured man loves a woman who knows her Northanger Abbey from her Sense and Sensibility. Plus, Austen pokes fun at women who try to snag rich men at all costs, and rewards those who look for both money and love. Which is why, back in the Smith College English department, we had a motto: WWJAD: What Would Jane Austen Do?

•  Bleak House by Charles Dickens. The first book to be sold in serialized form. HBO learned everything they know from Dickens.

•  Moby-Dick by Herman Melville. Just mention Ishmael setting sail from Nantucket, and hope that sends him into a diatribe about how Martha’s Vineyard is the far superior of the two islands.

•  The Scarlet Letter by Nathaniel Hawthorne. Resist the urge to make a Demi Moore reference.

•  Heart of Darkness by Joseph Conrad. By all means, make an Apocalypse Now reference.

•  Les Miserables by Victor Hugo. If you know all the words to “Castle on a Cloud,” you’re money.

•  The Mill on the Floss by George Eliot. Just shake your head, laugh, and say “Truly, the most befuddling ending in all of literature.”

•  Pale Fire by Vladimir Nabokov. Say “You have to admire the use of an unreliable narrator.”

•  The Catcher in the Rye by J. D. Salinger. You probably won’t have to say anything. Just nod knowingly as he compares the book to his freshman year at Choate.

•  The Stranger by Albert Camus. Let him know that the Cure’s “Killing an Arab” was inspired by this book.

•  Of Mice and Men by John Steinbeck. Giving new meaning to the phrase “I didn’t know my own strength,” Lennie accidentally kills a puppy and his boss’s wife. Proving once again that size does matter.

•  Atlas Shrugged by Ayn Rand. Describe it as “heavy.” You’ll mean that the damn thing weighs seven pounds. He’ll think you’re referring to the plot.

•  The Sound and the Fury by William Faulkner. If he’s from the South, change the subject. If not, just say “And I thought my family was dysfunctional . . .”

•  A Farewell to Arms by Ernest Hemingway. A tragic love story set against the backdrop of war. So engrossing, so captivating, and yet—when Henry proposes and his girlfriend Catherine says, “How could we be more married?”—clearly, a work of fiction (written by a man).

•  The Bonfire of the Vanities by Tom Wolfe. A satire of status-crazy New York in the 1980s from the ultimate social commentator/novelist since F. Scott Fitzgerlad.

•  A Heartbreaking Work of Staggering Genius by Dave Eggers. Or as a British friend of mine calls it, a heartbreaking work of staggering pomposity. Eggers, the founder of the hip and offbeat literary journal McSweeney’s, shows that he is no different from most young men—he can talk about himself for hours. And hours. And hours.

While we’re on the topic of reading, an easy and inexpensive way to stay updated on current events and culture is to subscribe to at least one Sunday paper. The New York Times is your best bet, and can safely be called a girl’s (second) best friend. I know women who’ve landed great husbands after they whispered over espresso that they love nothing more than to spend their Sundays curled up with the Times and a cup of coffee, even if they do start with the Style section.

I’d also suggest getting at least one additional (and educational) magazine subscription, on any topic that you want to learn more about. And by any topic, I don’t mean makeup or celebrity gossip. I mean a topic that will impress the sort of guy you want to marry. Think about it this way: if you read it, he will come.

•  Food and wine: Wine Spectator, Gourmet, Bon Appetit

•  Politics: The Economist

•  Sports: Sports Illustrated

•  Travel: Condé Nast Traveler, National Geographic

•  Art: Art Forum

•  Culture, current events, and literature: Harper’s, The Atlantic Monthly, The New Yorker

•  General trivia and facts: Mental Floss

Man-Proofing Your Apartment

You’re almost ready. You know what to wear, what to say, and what to cook for dinner. But before you meet Mr. Wonderful and invite him over for a romantic evening, you’re gonna need to man-proof your home. My Aunt Nancy told me that the first thing she did when she started getting serious with her then-boyfriend (now-husband) was upgrade her cable package so that she’d have access to all the major sports networks. I recently asked my uncle what he saw in her in those early months and without skipping a beat, he said, “We used to have so much fun sitting around at her apartment, watching TV and talking. It was just so comfortable.” Yup, and the ESPN 2 didn’t hurt either.

A man’s home may be his castle, but putting him at ease in your home might just be the key to cohabitation. Some other things to bear in mind:

Keep a six-pack of beer in your fridge. All men like beer. Men of a certain social status are rather discerning (read: snobby) about the brands they prefer. You’ll impress with any of the following: For foreign beers, go with Heineken, Stella Artois, or Hoegaarden. For domestics, go with Sierra Nevada, Magic Hat, or Sam Adams. The men I asked about this surprised me when they said (unanimously) that they’d find it odd if a woman had tons of obscure varieties of beer hanging around. So don’t worry about trying too hard. Basically, as one of them put it, “If she has something for me to drink that isn’t Smirnoff Ice or Mike’s Hard Whatever, then I’ll be happy.”

Invest in video games. I am in no way above improving my apartment just for the sake of a man. However, when my sister gave me the old-school Nintendo NES last Christmas, impressing dudes with it was the last thing on my mind. I came this close to quitting my job, just so I’d have more free time to play Super Mario 3. But a fabulous side effect of owning Nintendo is that every male who enters my apartment is instantly tempted to take up permanent residence on the couch. If you have any desire whatsoever to have video games (or men by the droves) at your place, buy an Xbox, PlayStation, or Game Cube immediately.

Hide the stuffed animals. Though you may still find all eight of your original Cabbage Patch dolls just as lovable as ever, they could cause the man in your life to get an acute case of the creepy-crawlies. Some women tend to accumulate toys and dolls and teddy bears over the years. I would never tell you to get rid of any of these things, especially if they have sentimental value. Just find a new place for them. Like in the back of your closet or under the bed.

Make the place comfortable. Though many of us conjure up images of the typical man’s apartment as dirty and under-decorated and the typical woman’s apartment as pristine and pink, I have never seen these distinctions play out in real life. Modern women are busy with work and friends, and those of us who live in urban shoeboxes don’t tend to entertain all that much anyway. But when you invite a man over (especially early on in the relationship), prepare in the same way that you would if you were having out-of-town guests. Make sure you have enough of the essentials—toilet paper, milk, fresh water, clean bath towels. Don’t leave the sink full of dishes, or the garbage overflowing. And don’t assume that just because he’s a guy, he won’t notice if your place is a mess. Even if it’s subconscious, he will be assessing what it would be like to live with you in the future by how you live now.

Clean your bathroom. I interviewed a dozen or so guys for a magazine piece about what happens when couples move in together. As one of them put it, “The bathroom is just one big hairball. I never knew my girlfriend had that much hair, and frankly, it scares me.” Be considerate and clean up after yourself in the bathroom when he’s coming over (and that goes double for when you use his bathroom).

Knowing It All

This chapter was meant to provide you with information and cheat sheets on a lot of important topics—important in general, but even more so when it comes to dating. It’s great for you to know a little bit (or a lot) about sports, wine, art, movies, and the like. But just remember: nobody can know it all. Sometimes it seems that we are programmed to always have an answer to every question. But if you haven’t read the book he’s talking about, or been to his favorite new restaurant, it’s okay to admit it. Part of the fun of meeting someone new who is your intellectual and economic equal is that you will have a chance to learn from one another.

Excerpted from Dating Up , by J. Courtney Sullivan . Copyright (c) 2007 by J. Courtney Sullivan . Reprinted by permission of Little, Brown and Company, New York, NY. All rights reserved.

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