Tonight, as I was out for drinks for my friend A’s birthday, I confronted one of my obstacles for the whole 100 emails/20 dates thing: I have several concurrent unrequited crushes right now.

There are two issues with all these crushes:

• I have trouble connecting with strangers. That’s why my more successful relationships have started off as friendships.
• I have trouble believing that my guy friends will like me. That’s why I am unable to transition friendships with potential into romantic relationships.

Stalemate.

D. brings up both of those issues. As soon as I met him, I immediately liked him; he’s smart, funny, a smart-ass, good-looking, has an interesting point of view, and a great voice. He meets the criteria. But I rarely have a decent conversation with him, partly because I know I have a crush on him and perhaps partly because people just don’t know what to make of me when they first get to know me. I’m a Gemini. I’m hard to pin down.

He joined up with us tonight at Dada, and for the first time in ages, we were actually conversing. I even achieved one of my goals, to not be so physically reserved. OK, so I punched him (jokingly), but it was physical contact, right? Progress!

But then he left to hang out with a girl who:

• Is skinny and cute
• Does not appear to be very bright (admittedly, I have only had limited interactions with her)
• Recently broke up with her boyfriend, with whom she was living
• Is significantly years younger than him

And therein lies the problem for women my age. Guys who meet all the criteria for a good boyfriend for girls like me are not looking for good girlfriends like me.

So really? I have to do Match? These friend crushes aren’t going to pan out? I am resisting this like Daniel Baldwin is resisting Celebrity Rehab.

I’m going to dip my toe into the waters on Craigslist first. I think I need to work up to Match.