As I headed over to Clyde’s for Happy Hour, I found myself rather apathetic about meeting Improv Boy. My apathy stemmed less from true disinterest than it did from my expectations of the evening. I hoped to enjoy the evening with my friends and get to know Improv Boy better. But, I didn’t see the night as the first step toward anything serious with him.

Quite a few of my friends were at Clyde’s when I got there. Within the next half an hour, a few more trickled into the bar. I was talking with Autumn, when Improv Boy arrived.

I stood up from my bar stool to greet him. I then introduced him to my friends, all of whom I had met through Twitter.

When he sat down next to me, he commented:

I figured that all of your friends would be lawyers.

Me [chuckling]: No. I only have a few friends who are attorneys. [I decided to spare him the reasons behind that, but I sensed that he had that impression that I was one of those people who chose the law for money, power or to follow in my father’s footsteps. None of those reasons were the case!]

As Improv Boy and I talked, it was clear that we had very different backgrounds. He seemed to have a lot of wanderlust and indicated that he might want to quit his job and go back to school or settle in a new city. He had also served in the military for over a decade with two tours in the Gulf.

That’s not normally the type of guy that I’m drawn to, but I decided to throw out my usual playbook. Nothing he said about his past or his uncertain future were negatives. I reminded myself that I could just get to know him and don’t have to over-think the situation.

I also didn’t let his appearance faze me. I definitely have a superficial side and like my men to fit a certain mold. Improv Boy is white and not conventionally attractive. His appearance and expressions are great for comedy, but as Autumn recognized:

He has a very big head and oddly shaped facial features.

I didn’t disagree with her, but as I continued to talk to Improv Boy, I realized something:

He’s not visually attractive, but he has a great personality and that makes him attractive!

We stayed at the bar during the entire Washington Capitals playoff game. Improv Boy was comfortable letting me socialize with my friends, but when I came over to him, he made it clear that I was his primary focus. He interacted well with the group and was interesting to talk to one-on-one. He insisted on paying, even though I didn’t view Happy Hour with my friends as a date. And, as one would hope since he’s a comedian, he had a great sense of humor. All of these things won points with me.

One Twitter friend, Adam, discussed the dating scene in DC with Improv Boy and me:

You just need to eliminate dating 30-35 year old women unless you want to get married or have kids. That’s all that they’re thinking about in this city.

Me: Really?!? That hasn’t been my experience. So, what is a better demographic?

Adam: 20-something girls are too young, unless you’re just looking for fun. After 35 is perfect since they already realize that they’re done. It’s too late for them to have kids so they’re just happy dating.

Me [laughing loudly]: Seriously?!? I totally disagree! But, it’s good to know that you’ve put me out to pasture. [Look at Improv Boy.] Apparently, you have nothing to worry about. I’m lucky to even go out on a date at such an old age. [The three of us laugh.]

The Capitals lost, and Improv Boy offered to put me in a cab. I told him that I prefer to walk home and he offered to accompany me.

Me: I’m really glad that you came tonight.

Improv Boy: Me too. I had a great time meeting your friends, but I hope that you’ll let me take you out on a proper date next week.

Me [smiling]: I’d like that.

As we were walking home, Improv Boy mentioned that he would be spending the weekend with his family.

Me: That should be nice! Do you have any kids?

Improv Boy: No.

Me: Oh…I thought that Abigail [my friend who does improv with Improv Boy] had told me that you had an older child.

Improv Boy: No, I don’t.

Me: Oh…sorry. It doesn’t matter to me either way. I was just wondering.

We changed topics for the rest of the walk home. Improv Boy asked if there was a place en route for him to use the restroom. I knew of one bar, and as we walked inside, I saw UConn Boy‘s best friend. (I keep telling you all that DC is small!)

He and I chatted for a few minutes while Improv Boy was in the bathroom.

Me: Oh, not to shock you, but I’m out with a white guy tonight. [We laugh, and I introduce him to Improv Boy.]

Ten minutes later, Improv Boy and I reached my building. He took my face in his hands and gave me a sweet, soft kiss. Picture open mouth and no tongue. It was just enough to make me want more, but not too much that it was inappropriate.

Improv Boy: Would you be free to go out this coming week or next weekend?

Me: This week! Sooner is better! [Smiling like a kid in a candy store.]

Improv Boy wasn’t my type, and I had a feeling that I wasn’t his. But, after dating quite a few guys who weren’t nice, I was finally ready for a guy who was.