Dinner With Cupid

But seriously, folks

Will this lighthearted pair wind up funny valentines?

Jon Brenner and Jennifer Twitchell.


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.

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Administrative assistant

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.




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.





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