On their Dinner With Cupid blind date, two humor lovers meet, laugh, and leave. But seriously, will they wind up together?
JON BRENNER > 22
Associate account manager
HIS “PERFECT DATE” INCLUDES Outdoor activities or going out for food and drinks
HE IS HAPPIEST WHEN I’m never not happy; life is too awesome.
JENNIFER TWITCHELL > 24
HER “PERFECT DATE” INCLUDES A restaurant that neither one of us has ever gone to
SHE IS HAPPIEST WHEN I’m with a few good friends . . . enjoying a beer or two.
7:30 P.M. BENEVENTO’S, NORTH END
JON I wasn’t nervous [before the date]. I was only curious as to what this would be like, as I had never been on a blind date.
JENNIFER [I was] very calm — I knew, if anything, this was just going to be a great way to meet someone new and have a good time.
JON I was mostly wondering if we would shake hands, hug, or what.
JENNIFER He was there before I was. He was sitting right by the door. I wasn’t sure if he was really my date. He was dressed pretty casually . . . like he was going to meet up with friends for a drink. That threw me off a little bit right off the bat.
JON She came in and immediately gave me a very professional handshake. It was off-putting at first, but we laughed about it later.
JENNIFER He had already ordered a beer before I got there, so we made some small talk and joked about how I went to the wrong restaurant first.
JON I thought she was attractive.
JON [Over dinner], we talked a lot about our own lives and things we had in common.
JENNIFER We both enjoy a few of the same TV shows, and [we] talked about the music we both enjoy.
JON We discovered we both work in real estate [and] we seem to have a similar sense of humor (I thought she was funny, and she laughed at most of my attempts at jokes).
JENNIFER [I felt] very comfortable. We both admitted that this was kind of a joke for us mid-date, so that definitely relieved any tension that may have been there.
JON Neither of us was looking for a relationship because we were both recently out of long ones.
JENNIFER Initially, I knew it wasn’t what I was looking for just based on the fact that he was wearing a hat at the dinner table, but . . . the age difference is what [really] got me.
JON We got along well [and] went to another bar afterward and had fun.
JENNIFER I hoped that we could still be friends and figured that going out with a big group after dinner wouldn’t send any mixed signals.
> SECOND DATE?
JON I want to, even though it’s not going anywhere; I just had fun with her.
JENNIFER No. We both realized that this wasn’t going to work out and that we weren’t really looking for anything. — Compiled by Peter Cocchia
GO ON A BLIND DATE. WE’LL PICK UP THE TAB. Fill out an application at boston.com/cupid.