The 5 people every man/woman should date

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5 women every guy's gotta date
By Jonathan Small

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.

With 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 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, Claire from Six Feet Under. 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.

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

5 guys every girl’s gotta date
By Maura Kelly

Wondering which fella to flirt with next? Make a point of getting to know these men—they can teach you wonderful things about life and love…

So you’re out on the town, looking for a cute guy you’ll click with…who’ll be the next lucky dude? Who’s your usual type? Before you answer, wait a second, and let us urge you not to date your usual type. You’ll benefit big-time by dating various types of guys. Here’s why: Each will stretch the boundaries of what you think makes a suitable mate and teach you a unique set of skills that will come in handy when you do meet The One.

Type #1: The Older Man
There comes a point in every guy’s life when he’s no longer interested in keg parties, Sony PlayStations, and phrases like “getting laid.” In short, a man becomes a man, and that’s exactly why you should see what an older guy is all about. No, it’s not because he could be a sugardaddy who’ll shower you with fancy meals and great gifts (although that could be nice).

The real perk of dating an older guy is his worldliness and wisdom, which is bound to rub off on you, says Steve Nakamoto, author of Men Are Like Fish: What Every Woman Needs to Know About Catching a Man. “Because he’s had more life experience and has been through more than younger guys, he can play something of a teacher role,” he explains, adding that he once dated a woman 14 years younger than him. “She still calls me today to thank me for the things I taught her,” he says. “She’s always been very appreciative of advice I gave her, even little things like buying a CD, after I explained that I meant certificate of deposit, and not a music album!”

Type #2: The Starving Artist
Okay, sure: These dudes are not going to take you to fancy restaurants or even pay for your half of the dinner bill. Money, nice meals, and material goods don’t mean squat to this guy—and that’s exactly why you’ll have an incredible time once he opens your eyes to life’s simpler pleasures. Erika Meitner of Charlottesville, VA, now sees the world differently after a summer spent with a struggling musician, Jesse. “We went on the best dates, because they all involved great conversation and the most unexpected adventures,” she says. “He knew all the best cheap beer bars, where the jukeboxes rocked, and colorful people always wanted to tell Jesse their stories.” Not only will the world seem infinitely fascinating, but you may feel more fascinating, too, as you become inspired by his creativity and perhaps play the role of his muse.

Type #3: The Metrosexual
OK, so he may be better dressed and more recently manicured than you. Get over it—because not only will you reap the obvious benefits of dating a guy like this (like being able to borrow his expensive shampoos), you’ll get a chance to live a happenin’ life! These guys will take you to all the hottest clubs and coolest clothing stores, and let’s not forget just how fabulous you’ll feel walking hand-in-hand with a man who looks like he just stepped out of an issue of GQ. The benefits don’t end there: His style may well rub off on you. “That’s significant,” says Nakamoto, “because it makes her feel better about herself, as well as making her a stronger player on the social and professional fields.”

Type #4: The Bad Boy
This rebel might have a motorcycle or not, but one thing’s for sure: He lives on his own terms and is not about to apologize for them. Hang with him for a while, and you’ll learn why being bad can feel so good—and how to stop worrying about what everyone else thinks. Talk about liberating! “In general, women tend to be pleasers, much more so than men,” Nakamoto says. “A bad boy can show them what it’s like to quit trying to make everyone else happy, and just do what you want.” New Yorker Diana Petroff has first-hand experience with these bad-boy benefits, having once dated one of these rebels. “He knew there was more to the world,” Petroff explains. “And from being with him, I learned to look deep inside myself for what's truly important—rather than just accepting what my parents or friends thought was the proper path for me.”

Type #5: The Nice Guy
He never makes you feel insecure or uncertain, never plays hard to get, never makes you doubt how he feels about you. It’s a shame that we need to explain this one, and yet we know how hard it can be to date a true sweetheart, at least at first. “A woman won’t be used to the frequency and consistency of affection nice guys give, since most other guys who are playing the dating game don’t do that,” Nakamoto explains. Even so, he advises that women get used to the nice guys, and quick. Why? Because once you’ve had the good stuff (a guy who calls when he says he will; a guy who wants to see you more often as he gets to know you), you won’t stand for anything less. At the same time, that doesn’t necessarily mean you should start sending out the wedding invites after a few months. “Just because he’s nice doesn’t necessarily mean he’s the right guy,” Nakamoto warns. “He might rate low in terms of romantic chemistry, because he lacks the edge that creates the kind of surprise, passion, and excitement that all people want in their lives.”

Of course, the key is finding the man who has everything you want—until then, however, go ahead and try everything and don’t worry so much about whether you’ve found Mr. Right. Trust us, he’s out there. In the meantime, have fun!

Maura Kelly is a freelance writer living in Washington, D.C. who’s written for Glamour and other publications. While she’s dated all of these types, she most highly recommends The Nice Guy.