7:30 P.M. | RISTORANTE LA PERLA | WEST END
Ray: I dressed maybe 10 percent nicer than normal. I got to the restaurant 5 to 10 minutes before Anne and sat at the bar. A bottle of Frangelico was calling my name: Ray, you love hazelnut. Yes, I do, bottle. So I had a Frangelico and coffee.
Anne: I had a crazy day, so I went straight from work. He was already there. He's cute, but he's got a little pudge. That wasn't a make or break, but it was a bummer.
Ray: She bears a striking resemblance to Kate Walsh from "Grey's Anatomy," or a mix between her and Cynthia Nixon. Definitely attractive and in good shape.
Anne: We made our way to the table and started talking. He's a goofball, sort of a Jim Carrey caricature. It's funny -- but not in an endearing way.
Ray: I was a radio disc jockey for eight years, so I randomly break off into strange voices that I don't even know I'm doing half the time.
Anne: We talked quite a bit. I told him about my global travels. He'd lived in a lot of different American cities, so that was interesting. After the first 30 minutes, my impression of him started to get better. He's clearly highly intelligent and really nice.
Ray: We shared a bit of each other's meals. One funny thing: She had a tote bag that had pink elephants on it. I said, "Wow, they have a drinking club, like you drink so much you see a pink elephant?" She laughed. I had no idea that she was a Young Republican.
Anne: He wasn't listening. I'm not part of any Republican women's group. I just saw it on the RNC Web site, and I thought it was a really cute bag for the summer.
Ray: There was [chemistry]. It was very easy to talk to her. And she made sure we did these German-style toasts -- you look somebody dead in the eye and toast -- whenever a new beverage [arrived]. It was charming.
Anne: There was some chemistry; I think the beer helped. We were having fun. He was like, Do you want to get a drink afterward? We ended up going to Brickskeller.
Ray: Once there, she told me a story about her aunt getting into an elevator in Atlantic City with two large, black men. One said, "Hit the floor!" So the aunt [drops], thinking she's being robbed. [But he just meant, hit the elevator button.] Later, she finds out the men were Michael Jordan and Magic Johnson. Midway through Anne's story, I was like, I've heard this before; it's an urban legend. But you don't want to say, "Your aunt's a liar." So I said nothing. Around midnight, we headed out. Since she lived close to me, I dropped her off. We hugged goodbye.
Anne: Oh, my God, I can't believe my aunt told me this -- though she said it was her friend -- and I repeated it! It's nice that Ray didn't say anything. I'd rate the date a solid 3, possibly a 3.5, out of 5. I had a really fun time, but the first impression really influenced me. That and the listening thing.
Ray: It was a 5, easy. We got each other's number. I'm definitely going to e-mail.
Interviews by Christina Breda Antoniades
Update: When Ray e-mailed for a second date, Anne politely replied, "I just don't think we're quite the right fit."
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