For our first one-on-one date, Improv Boy suggested dinner in the city. That was perfect for me! I texted him to inquire if I should wear jeans or a skirt, and he responded: jeans. I typically date guys who wear more suits than casual clothes (and who would always want to see me in a skirt) so this was new for me. But, I reminded myself that dress doesn’t really matter and just put on a cute pair of jeans.

When Improv Boy picked me up at my place, he asked if I would like to take a cab or walk to Georgetown. I chose, as I often do, to walk. While walking, he reached over to hold my hand. That was sweet, and I tried to give him a chance. But, as I looked at him, I wasn’t sure if I was attracted to him physically and personality-wise. He was really white. (And, yes, I know that I’m white.) But, I don’t tend to date white guys.

Improv Boy and I walked up 31st Street. He stopped in front of a restaurant, Paper Moon, and said:

I love Italian food.

Me: Me too.

Improv Boy: I was torn between this place, Papa Razzi and Piccolo, but I thought that Piccolo would be best.

Me: Great!

Me [what I thought to myself]: Paper Moon – the place where I used to go salsa dancing as a college intern? And, Papa Razzi, where I went once in 1998 and my Armani pants got stuck to the table because there was a wad of gum underneath? [Yes, that really happened.]

Piccolo was definitely the best choice out of the three, but none of the restaurants were truly Italian. I tried not to be a food snob, though, or knock a gift horse in the mouth. After all, Improv Boy wanted to take me out on a date. “Buckeyes” Boy lived with me for three months and only bought me breadsticks.

The maitre d’ showed us to our table on the balcony. The restaurant has only three tables for two on the balcony so it’s quite romantic. The weather was also perfect for dining al fresco, as is often the case in late April.

As Improv Boy and I talked about life, work and past relationships, I realized how little we had in common beyond sports and the arts. I wasn’t bored, but I didn’t sense much of a connection. I felt more of a friendly vibe with him, rather than a romantic spark.

We got into a conversation about being friends with exes since that’s important to both of us. We both make an effort to try to be friends with our former significant others. However, Improv Boy has a lot of back-story: an ex-wife; a girlfriend that he lived with; and an ex-fiancée.

Improv Boy: Were you ever married before?

Me: No.

Improv Boy: Any kids?

Me: No, but I’ve started looking into the process to adopt a school-aged little girl.

I spoke for a couple of minutes about my plan. Normally, I wouldn’t bring this up with a guy so early on out of fear of scaring him off. But, I really didn’t see this date going anywhere. Improv Boy made a kind comment that I would be a natural as a Mom. He then told me that he did in fact have an older child.

Improv Boy: I’m sorry that I lied to you on our walk home from Clyde’s, but I wasn’t prepared to talk about it then.

He then briefly explained that he was estranged from his 18-year-old daughter. I could tell that the topic brought him much pain. I didn’t want to judge his situation since I didn’t know many details, and yet, I couldn’t help wondering why his teenage daughter didn’t want him in her life.

Improv Boy was a total gentleman during dinner, sharing his food with me, making sure I had everything I needed and paying for the check. He was a very nice date. As we walked home, though, I wondered: how nice was too nice? Could I really be attracted to a guy like Improv Boy? Were our backgrounds, goals and interests too different?

Once we arrived at my door, that should have been the end of the date. It didn’t seem as though we were a match. And, yet, the date was far from over.

To be continued…
xoxo