Dear Wendy: “I’m Pretty, So Why Can’t I Get A Boyfriend?”

I’m a smart, attractive 20-something living in NYC and am miserably single. Thanks to my parents’ golden gene pool I have no problems attracting male attention, but somehow the men I date end up fading out after a few dates. While all my girlfriends are in love with their amazing boyfriends who adore them, I am constantly out man-hunting at the nearest hot spot only to end up with a stud for a two-week fling. I’m social and funny, and not a psycho or vain or self-involved. I have plenty of cool male friends who agree that I’m a great catch, so what gives? I always end up dating very attractive guys with dating ADD or less attractive guys who claim they’re too intimidated to be themselves around me (lame). To make matters worse, my past two boyfriends left me for women who are significantly less attractive than I am (plain, tom-boyish types) and are in healthy long-term relationships.


I’ve heard tons of theories from my girls who don’t understand why their “prettiest friend” is always single. The reality that I may be the problem has taken a toll on my self-esteem, and I’m realizing I’m slowly becoming one of those dreaded boring pretty wallflowers with nothing interesting to say (less I utter something wrong and offend a potential mate). Now it’s gotten to the point where my dating habits are becoming self-destructive. I have been drinking more and filling my weekends with one-night stands to make myself feel better, and if a guy does seem interested in more, I sit there and psychoanalyze him down to the jerk that I know he is somewhere deep down. I’ve even begun resenting my friends in relationships because of my seething jealousy. I hate this person I’ve become but know I deserve someone great. How can I get out of this rut and get back to being me again and use my assets to the best of their ability like the rest of sex-crazed America? — Pretty Insecure

Well, for starters, what makes you think you “deserve someone great”? I’m not trying to be snarky; I really want to know. So often, most of us think we “deserve” stuff — love, happiness, a great life — simply because we’re alive and breathing. Or because we aren’t, like, horrible, awful people. Or, because we had such crappy pasts, karma owes us something. Or … because we’re pretty. But is that really true? Can you imagine if we applied the same logic to something like a job or a promotion? Can you imagine sitting in an interview and saying, “I deserve this job because, well, for one thing, I’m alive. Also, my last job was really terrible so I’ve definitely earned something better. Plus, I’m not a terrible employee … and, well, just look at me!” You’d get laughed right out of the office!

Potential employers don’t want to hear that stuff. They want to hear what you have to offer them — how you plan to make their lives easier and better. And you know what? Potential love interests — at least, the high quality ones that you claim to want — aren’t that much different. They want to be with someone who has a lot going on … not someone who’s obsessed with her appearance, spends weekends drinking herself into oblivion, has nothing interesting to say, believes people to be “scum” without getting to know them, and is already jaded at the tender age of “20-something.” Would you want to date that person? What about that person signifies someone who is deserving of great love?

Look, I don’t know you. I’m just going by how you’ve described yourself and I can say if your description is right, it’s no wonder you can’t keep a guy around. Have you ever heard the expression “you have to be a friend to have a friend”? Well, the same idea applies to romance. You want to find a great person to date? Well, start with being a great person. That means working on yourself. Find better, more productive ways of filling your weekends than indulging in meaningless one-night stands that leave you feeling empty. Develop some interests, passions, and hobbies so when you go out and meet new people, you’ve got something to talk about and you aren’t that “dreaded boring pretty wallflower with nothing interesting to say.” Open your heart up and start seeing guys not as simply attractive but flawed people, or less attractive but intimidated characters, but as real live human beings with their own dreams and desires and weaknesses. And if you aren’t ready to get to know them as unique individuals — if you’re too jaded to let your guard down and quit psychoanalyzing the balls off them — take a break from dating until you are.

And here’s one more tip: When you decide you’re ready to get back out there and start your “man hunt” again, don’t go searching at the nearest “hot spot.” That’s not where the quality guys looking for long-term, committed relationships hang out. Instead, ask some of those “cool-ass male friends” of yours to introduce you to some of their friends. Hit a dog park. Go to the book store. Hang out in coffee shops. Take a cooking class. Join a singles group. Go to the gym. Quality men are everywhere. You just have to be open to really seeing them and reserve judgment until you get to know them.

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*If you have a relationship/dating question I can help answer, send me your letters at {encode=”dearwendy@thefrisky.com” title=”dearwendy@thefrisky.com”}.

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