JOSEPH CAPUTO > 26
WHEN HE’S HAPPIEST On a warm night in the city with a drink and a good friend
WHAT MAKES HIM A GOOD CATCH I find people inherently interesting. I like asking a million questions, finding out what is meaningful to someone.
WILL DOWD > 26
WHAT HIS EXES LOVED I am a gentleman.
COMEDIAN WHOSE HUMOR HE SHARES David Sedaris
WHEN HE’S HAPPIEST When I’m with family, no ifs, ands, or buts about it
7:30 P.M. FINZ, SALEM
> BEFORE THE DATE
WILL I went with a casually dressed jeans-and-scruffy look. I look older when I don’t shave.
JOSEPH I made sure to straighten my hair so I didn’t look like I just woke up from the ’80s.
WILL I entered this experience with the mentality of “A stranger is just a friend I haven’t met yet,” which helped calm me down.
> A SECOND CHANCE
JOSEPH The second I saw it was the Will I knew, I put my head in my hands and laughed. We didn’t exactly leave off on the best of terms last time we saw each other. I had even blocked him on Facebook.
WILL When I got to the date, I had an inkling that it might be Joseph. And turns out I wasn’t wrong. I went over and gave him a big ol’ hug.
JOSEPH Will looked a little bit like a frat boy. I have found [him] strangely attractive since we met.
JOSEPH I was really impressed with Finz. I didn’t once feel uncomfortable because it was a “gay” date. There were even rainbow flags on the wall. Will and I shared some oysters, which were amazing. I would go back.
WILL We talked about the serendipity of the situation.
JOSEPH I was definitely a bit on the defensive, but Will was very respectful of my feelings so I eased up.
WILL I think the conversation could best be described as a tennis match, volleying back and forth without either of us dominating the conversation, which I really think is hard to come by these days. We talked about recent US Supreme Court decisions, supernovas, regional politics. . . . I think Snooki was in there somewhere.
> LIKE OLD FRIENDS
WILL As the night went on, he did seem more attractive, intellectually.
JOSEPH The time just went by. I think we left when neither of us could stay and eat any more.
WILL I could tell he was listening to me when I spoke.
JOSEPH The whole night seemed like something out of a one-act play.
JOSEPH A. This could have been a fiasco, but it was a surprisingly great evening.
> ANOTHER DATE?
JOSEPH I would, but we’d have to take it slow.
WILL I don’t think the next time we hang out we’ll go on a “date.”
— Compiled by Andrew Doerfler.GO ON A BLIND DATE. WE’LL PICK UP THE TAB. Fill out an application at boston.com/cupid.