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5 Women Every Guy’s Gotta Date


Before settling down, these are the gals every man should date. Why? For the connection you two feel, of course, but also for the relationship lessons each one will teach you.

By Jonathan Small

ith so many amazing women out there, how do you know which one is right for you? The honest truth is, you don’t really—that is, unless you get out there and date. “Men should experience dating many different types of women before they settle down,” says Gilda Carle, Ph.D., a New York-based relationship expert. “The more relationship skills you learn and the more experiences you have, the more prepared you’ll be when true love finally comes.” So, allow us to present five women you really should date before you say, “I do.” Of course, no one is saying you should go through life with a little checklist titled “Women to Date,” but spending time getting to know and appreciate these women can be a wonderful thing. Here, a look at who they are and why you should go out with them.

Type #1: The Older Woman
If you haven’t tried dating up the age chain, you don’t know what you’ve been missing. Mature women have been places, seen things, and have a sophistication and wisdom that you, my young friend, can—and should—soak up like a sponge. “Older women know who they are and what they want,” explains Dr. Gilda. Spend time with one and you’ll gain a terrific perspective on life, and realize that being a desirable woman doesn’t mean being a woman younger than you are. Says Patrick Hayden of Seattle, WA, “I definitely recommend dating an older woman. I dated one when I was 19 and she was 30, and what she taught me carries over to this day.” While a knowledge of wine, travel and the human condition are usually par for the course, so is something else: a tutorial on how to please a woman in bed. “The older woman I dated was like a sex mentor to me. She taught me absolutely everything I know,” recalls Patrick.

Type #2: The Guy’s Girl
Every guy needs to experience that rare breed of gal who looks and talks like a woman, but loves sports, beer, and action flicks—in short, who acts
Dating a guy’s girl will make you realize that there’s no reason to walk on eggshells around women.
like a guy. Evan Silver is dating this type right now and couldn’t be happier about it: “She’s a hot woman who plays rugby and encourages me to hang out with my guy friends,” he says. The guy’s girl is often so similar to you that you forget to censor yourself around her—a good thing, according to Dr. Gilda, because it causes you to be more comfortable around women in general. “You’ll let your guard down more, just as you would around your guy friends,” she says. “You’ll learn that women can offer you friendship that you don’t have to reserve for your own gender.” We’re not saying you’ll be staging belching contests with all your future loves, but you will realize that there’s no reason to walk on eggshells around the person you’re dating. You can just be yourself—which is all women want anyway.

Type #3: The Free Spirit
This girl always stops to smell the roses. Think Drew Barrymore, Goldie Hawn or Kate Hudson. She’s totally creative, spiritual, spontaneous — maybe a tad ditzy — and she relies more on instinct and inspiration than reason and good planning. Why is this good for you? Because let’s face it: Guys are goal-oriented. We like game plans and spreadsheets; road maps and instruction manuals. That’s why sometimes we need a free spirit to fly into our lives and shake us free of our rigid ways. “A woman like this can tap a man’s creativity in ways no one else has,” says Dr. Gilda. “She shows him that not everything has to be perfect or planned.” Michael Pagliughi of Ocean City, NJ, concurs. He considers himself a tad uptight—and says that his art-student girlfriend taught him to chill. “She took me to some underground art galleries, had me stay up to the wee hours even when I had to work the next day,” he recalls. The spontaneity she taught him has carried over into other relationships. “She really helped me discover a more romantic, creative side of myself,” he says. “Now I’m much more likely to meet a date somewhere unexpected or surprise her with flowers.”

Type #4: The Brainy Chick
In the dating game, looks often trump intelligence—guys go for hotties rather than girls who can stand their ground in a heated debate. This is really a shame, since not only can the sharp ones keep your mind from turning to putty, they can help you appreciate all facets of a woman and even handle those times in your life when you don’t know it all. “Men are so often intimidated by smart women—they have vulnerable egos and never want to feel as if any woman is showing them up,” says Dr. Gilda. Sure, dating a woman who can beat you at chess or argue circles around you about Middle East politics might be a bit of a blow to your ego at first, but ultimately you’ll grow from it. Michael of Austin, TX, recalls his brainy ex-girlfriend this way: “She taught me how to debate with the best of them. I had to bring something to the table or she’d get bored. She challenged me in a way I wasn’t used to and that felt great.”

Type #5: The Seductress
Every man fantasizes about dating a girl who has an, um, healthy libido and is extremely creative in bed. The good news: These girls actually exist—and if you date one, you’ll be a much better man for it. But it’s not for the reason you might think. Says Dr. Gilda, “Every guy needs to get this type of girl out of his system. Because he’ll quickly realize that sex alone cannot sustain a relationship.” Evan can relate; he dated a girl who lived and breathed sex. “It was cool at first,” he recalls. But soon he began to want something more. “There was nothing else there, no romance and not much conversation,” he says. “I realized the only connection we had was sexual.” Evan has since moved on from the seductress, but he learned a ton. Sure, hot sex still ranks high on his wish list, but now he also wants a girl he can also really relate to and bond with. And that’s a very valuable lesson.

Want to hear the other side of the story? Check out 5 Guys Every Woman’s Gotta Date


Jonathan Small is a freelance journalist based in Los Angeles. He has dated each of the above women—and vouches for them all.
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