Mr. Unavailable #100: The Downtown Hipster

Vital Stats: 35, 5'7"ish. Slight build yet bearded and swarthy. Surfer. Landscape Architect. Income via freelance work and unemployment payments (Full Disclosure: We have the unemployment part in common--minus the freelance work part and payment part.)

First Date: We met via the OKCupid dating site, and, after a few weeks of delay, agreed to meet up at the Soho bar Sweet & Vicious at around 6 p.m. on a Wednesday.

First Impression: He was late to the bar and, when he arrived, he sauntered up, unmistakably coming across as the 2010 version of a hipster. It was the thoughtful combination of fingerless gloves, robber-knit cap and black skinny jeans that gave him away. He had a studied nonchalance in the way he curled over the bar or hunched toward me.

He was nice and kept me at the bar with questions about my friends, family, etc. I told him about some upcoming interviews and congratulated him on finagling a way to collect unemployment and money from freelance work at the same time. I think that's a hipster requirement: knowing how to work the system--or at least looking like you do. I was truly impressed.

I couldn't tell if he was interested, but he seemed disappointed when I suddenly announced I had to go. (Sometimes I'm not graceful about these things. I had some friends to meet later on, but never mentioned it, figuring he'd think it was an out. Although suddenly having to go was probably just as suspect of an exit.)

He was on his second pint when I made my announcement and said he was going to stay for a third. I left the bar and, walking down the street, called Shelagh, telling her I was feeling like it wasn't a match and like he was too much of a heavy drinker for me. She could relate. She was in the thick of a relationship with a heavy drinker. Still, I felt a little sad about it.

Signs of Hope: When the dating site originally matched us up, he contacted me quickly. It took about a month for me to write him back (He'd written at the end of November and, at the end of December, I saw his note and thought, "How'd I miss him?" The short answer: Between November and December, I'd become more open-minded.) After I messaged him, it took a lot of back and forth to set up our first date, but, giving him the benefit of the doubt, let's just say the holidays got in the way.

Red Flags: Call me prejudiced, but the whole hipster thing is a big red flag. If I ever see his apartment and it turns out he has vintage furniture or taxidermy, then I get to say a big, "I told you so."

Turning Point: He must have detected my lack of interest because a few hours after our date, I got an email from him that suggested we could be friends. "Don't be a stranger," he wrote. To tell you the truth, when I got the email, I actually thought it was pretty sweet and do, in fact, want to see him again, which surprises me.

Diagnosis: For him: He may be an emotionally unavailable hipster, but, right now, he's interested.
For me: Sometime between Thanksgiving and Christmas of 2009, I became just a little more emotionally available myself.