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How To Wow An Older Woman


Hey, guys, are you younger than your new sweetie? You are not alone! Here are the rules of this new kind of romance.

By Jon Wilde

eck, if a man like Nick Cannon will pass up budding starlets for divorced diva Mariah Carey, there must be certain upsides to a woman of experience—and not just in her, ahem, bedside manner. “It’s a huge allure for young men because here’s a sophisticated, attractive woman in control of her own life,” explains Valerie Gibson, author of Cougar: A Guide For Older Women Dating Younger Men. “Often, she doesn’t want to get married and doesn’t want children. For a young man, she’s a sexy, exciting companion.”

If you’re dating a woman who’s older than you — or are open to the experience — you need to learn the rules of this kind of romance. To help you along, here’s advice on how to impress a woman of a certain age.

Do talk her talk
Your more experienced date may very well be able to party like a coed, but at some point she’s going to want to relax with a drink and — uh-oh —talk. “Above everything, an older woman would like to have a decent conversation,” advises Gibson. Problem is, with a
If you want to land an older woman, the only time you should be playing games is when you turn on your Xbox.
generation gap, you’ll have to work a bit harder, since gems like “What’s your major?” and “Did you see the new O.C.?” are suddenly moot. Ask her questions about her job, her hobbies, what type of music she likes. Just don’t be discouraged if you can’t find common ground. So what if she’s a wine enthusiast, but you’re a beer man? Ask her to pick out a glass of red she thinks you’d enjoy. Accept that this relationship, however serious, will be built less on common ground and more on exploring new territory.

Don’t play around
If you want to land an older woman, then the only time you should be playing games is when you turn on your Xbox. That means ditching those dating rules you developed in high school—like waiting days to call in order to make yourself look cool. “The wonderful thing about being older is that you just don’t have time for games,” explains Sarah Winter, coauthor of Older Women, Younger Men. “If a guy tries that three-day rule, I’m already thinking he’s too insecure to handle a relationship with me.” The solution’s simple: Just act like you feel, not how you think you should according to some Seinfeldian dating protocol. If you like her, say so. If you want to call her, do it. Since an older woman is more likely to be further along in her career than you are, she may insist on paying most of the time, but do be a gentleman and offer to buy dinner. And if she calls you, don’t wait until the fourth ring to pick up, Fonz. (If you don’t get that reference, feel free to ask her.)

Do stay cool
Burt Reynolds and a 19-years-older Dinah Shore made waves in the ‘70s when word broke that they were an item, and 30 years later the public still goes slack-jawed over Mariah Carey and Nick Cannon—proving that the older woman/younger man relationship may be the last taboo in dating. And the uncomprehending responses aren’t confined only to Hollywood love lives. You’ll have to deal with looks and remarks from friends, family, and even strangers. “Don’t date an older woman if you can’t handle that attention,” advises Gibson. But if you’re deft, you’ll not only cope, you’ll impress your lady with your maturity and charm. That stodgy couple one table over insists on gawking? Turn, smile, and smoothly say, “I don’t blame you for staring. She’s beautiful, isn’t she?”

Don’t mention the numbers
You don’t need to be a mind-reader to know that women, no matter how poised and confident, aren’t keen on being reminded of their age. In this case, that also means not
Fact is, if she wanted to date a man her age, she would.
constantly referencing the spread between your years and hers. A line like, “It’s so great that we get along despite the generation gap,” sounds good in your head, but comes across as, “I’m glad we get along even though you’re so old.” Besides, it’s your personalities, not your birthday candles, that are compatible—and that’s what you should concentrate on. So please, avoid asking questions like, “Did video games exist yet when you were a kid?”

Do act your age
Fact is, if she wanted to date a man her age, she would, so don’t pressure yourself to act more sophisticated than you are. “Younger men knock themselves out of the box psychologically because they think they have nothing to offer,” explains Winter. “But the reason that somebody like me is attracted to a younger guy is that their minds are more open. They offer spontaneity and fun.” When 24-year-old Beecher Smith-Stackhouse met a woman twice his age at a San Francisco bar, he didn’t think she would be interested in hitting a nearby house party that his friends were throwing later that night. “When I mentioned it offhand, she just lit up and said, ‘Let’s go!’” he remembers. “We ended up doing shots and making out in the hallway.” Here, exploring her “less mature” side can be a huge kick—for both of you!


Jon Wilde is an editor at Maxim.
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