13 12 / 2010

ask emmy. part five.

Dear Emily,

Today is my 27th birthday, and I am getting tired of being single. I’m decent-looking (according to friends), kind, a good cook, I own my own company and am a generally very well-rounded, highly intelligent man. That said, in the past 10 years, I have been in only one relationship and for less than one year.

The pattern is that I form very close friendships with smart, attractive woman and fall madly in love with them, but they see me as a “friend” and only in a platonic light. They laugh and say something like, “But you’re like my brother,” and in many cases we then grow distant. Or they ask my advice about men they are interested in — what can be more depressing than that? Especially when they tell me they like me better than they like him.

So what am I to do? I want to learn what I was supposed to have learned in high school — let alone the sexual experimentation that I should have done in college.

I dress in style, am clean shaven, hold doors open for women, bring flowers when I meet them at the airport, so what more do I do? And how to get women to be both friends and lovers?

Perplexed

—-

Nice guys finish last. I’ve heard these complaints my whole life from many of my male friends. I’m actually kind of excited to respond to this in a forum where you can’t talk back to me. The problem with these “nice guys” is that they always have an excuse. There’s always a reason they can’t take the advice they get. I get SO frustrated because there is no pleasing these men. Nine times out of ten, they are pursuing women who aren’t interested in them and ignoring or rejecting women who are. If this is the case for you, Mr. Perplexed, I hope you continue to be sad and single. That might sound harsh, but, seriously, if you’re treating women the same way you’re being treated, you can’t complain.

If that’s NOT the case, I only really have one piece of advice for you. You say the pattern is that you form close friendships with women and then you fall in love with them. Most experts will tell you that you need to be friends before you should be in a relationship with someone. I agree but you have to go about things differently. Express your interest immediately so the woman knows you’re not interested in a just-friends relationship. Ask her on a date as soon as you know you’re romantically interested. Don’t be shy. Don’t be coy. Be straight-forward, aggressive, confident. The friendship can continue to develop, but you don’t get put in the friend zone because the woman knows you want more. She can decide from there if she wants to date you.

I’m tempted to ignore your comment about sexual experimentation in college that you didn’t do… but I gotta just say one thing. I assume that means you want many different experiences with different women. If that’s not what you mean - if you want to experiment within a relationship - disregard this. If you’re trying to experiment sexually, why are you trying to be in a relationship? Pick one.

And stop feeling sorry for yourself. Lots of people your age are single and it’s not that big a deal. Don’t try so hard. Let things happen naturally.