Jesse Conklin, 23, Construction manager
Stranded on an island he’d want: The Internet, his bike, and WEEI
His perfect Saturday: Morning bike ride, afternoon Bruins game, nice dinner and barhopping
Sarah Merlin, 22, Web designer
Her perfect Saturday: A bike ride or a run, then relaxation before dinner and drinks with friends or a romantic date
Says she’s a catch because: She’s always looking for the next adventure.
7:30 p.m. Post 390, Back Bay
BRIGHT EYES Sarah: I got home from work early, so I took my time getting ready. I had picked out my outfit the night before.
Jesse: I had to work late, so I had just enough time to get ready.
Sarah: On the T to the restaurant, I did blast some pump-up tunes.
Jesse: I was a little nervous about who the date could be. I decided to take a seat at the table and look at the beer menu. I kept looking over to see who was coming up the stairs. She arrived a couple minutes later.
Sarah: I was relieved when I saw him. I thought he was pretty cute. The first thing I noticed was that he had really nice eyes.
Jesse: She came right in smiling and looking to have a good night.
GETTIN’ THE DIRT Sarah: We talked about the restaurant and how good the mixed drinks were. I’d been there a few weekends prior.
Jesse: We discussed our jobs and how tough the current job market is.
Sarah: We talked about one of his friends who works security at a big hotel downtown. I’m a sucker for celeb gossip, and he had some good stories about celebrities who came to Boston.
Jesse: We both enjoy riding bicycles. She participated in last year’s Pan-Massachusetts Challenge, so we talked about what it takes to ride it and how to train for it.
Sarah: He’s an engineer, and I went to an engineering school. We both love the Pats. We both enjoy what we do.
Jesse: She asked great questions that kept the conversation going. I can be shy sometimes, so this helped a lot.
Sarah: I realized we had a lot in common and a lot of fun and interesting stories to share with one another. Nothing felt forced -- it just seemed really natural and flowed well.
Jesse: That smile that first caught my eye kept looking better.
Sarah: He definitely got more attractive as the night went on. I figured when he wanted to order dessert, things were going as well as I thought.
CHIVALRY ISN’T DEAD Sarah: We went out on a Monday night, so we both had to wake up on the early side for work the next day. Even though he lived close to the restaurant, he walked me to the closest T stop, which I thought was really sweet.
Jesse: We exchanged numbers and discussed the possibility of another date.
Sarah: We hugged goodbye -- twice. A hug was very fitting for our date.
POST-MORTEM Sarah says: A. Best first date I’ve ever been on!
Jesse says: A-
A SECOND DATE? “I think we’ll go out for another date,” Sarah says. “We had great conversation and a lot in common. Plus he’s pretty cute!” Jesse agrees that they connected well.
GO ON A BLIND DATE. WE’LL PICK UP THE TAB. To apply for Dinner With Cupid, fill out an application at boston.com/cupid. ![]()



