I’m bad at dating

I can confirm, by the way, that updates posted on Wednesday's addict letter are legit. I think she posted them at the end of the day.


Please help me get back in the dating game. I have little experience being single and have primarily always been in relationships. As a result, many women who may have been attracted to me had I been single have now grouped me into the "friend zone."

Fast forward to present day. I'm single (under 25), work long hours, and have little time to meet new people. When I do, I focus too much on my own flaws. I feel I have little to offer them and sometimes don't initiate anything further.

My main issue is confidence. I am told I dress well, I'm no model obviously but I'm not a bad looking guy, but I feel I can't compete with the rest of the single guys who are accustomed and know the ins and outs of the dating world. Being single and meeting new people is scary for me, and I've spent the last year feeling as if I'm never going to meet anyone. I feel as if I can't compete with Mr. X who has supremely high confidence, and more experience. Women I deem attractive intimidate me, and I often won't pursue them because I feel as if they won't give me the time of day.

As a result, I tend to settle for girls I feel are more "on my level" even when the women I really would like to get to know (see: more attractive in terms of what I seek, more accomplished career-wise) may be more along the lines of what I am looking for.

My question: How do I resolve my confidence issues (counseling, therapy, going on a few dates?) and is there a more efficient way to meet new people than online dating or the bar scene? Am I setting the bar too low?

Any help, from you, the readers, I assure you is greatly appreciated.

– Looking For Love In All The Wrong Places, Boston

This letter reminds me of a letter from January. It was from a guy having a meltdown about something that makes everyone feel meltdown-ish. There's really no way to be a dating pro. No one knows exactly what they're doing. We all worry about being stuffed in the friend zone. We're all equal in this.
I do want you to think about what it means to look for a partner. I receive a lot of letters about standards and "setting the bar too low." My question to you is: Why is there a bar? You shouldn't be categorizing people based on whether you think they're too good for you. You shouldn't be labeling other men as peers or possible threats. Dating isn't about finding someone who meets a set of standards. It's about finding someone you like to be around who wants to be around you too.

So that's my advice. Find a group of people, men and women, who are good company. (You can join teams, alumni groups, etc.) Then think about whether you like any of the women more than the others (enough to kiss them). Don't think about their on-paper statistics. Don't think about what you offer them. Just think about how you get along. That's what matters here.

You're welcome to go to a therapist and talk about your confidence, but your problem is really about how you perceive the dating world. It's not a competition. It's just about finding someone you like.

Readers? We do get a lot of letters about dating and standards. Is that the right way to look at the dating experience? Can you give this guy a reality check? Help.

– Meredith