What’s up with that?

Sunday’s Dinner With Cupid column was a classic case of wishful thinking — by the editors, it turns out.

We matched Jaclyn, a teacher who comes across as mellow and fun (she loves yoga and wine, she says in her application, and she’s spontaneous), with Jon, an analyst who includes intelligent conversation and making out on his list of things he would do on the perfect date. The 29-year-olds were definitely different, but seemed from their answers to our questionnaire like they might meet exactly in the middle.

Then, on their blind date, theywere clearly comfortable with one another — he even tried her food.

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But afterwards Jon told us he just didn’t feel a connection. What went wrong?


Grade school teacher

INTERESTS Traveling, yoga, reading, cooking, wine

WHY SHE’S A CATCH I am genuine and kind, fun and spontaneous.

ON A DESERT ISLAND, SHE’D NEED Music, a book, a sundress


Telecom analyst

WHEN HE’S HAPPIEST When I am upside down in the middle of a back flip

HIS PERFECT DATE Funky cocktails, jazz music, sweet views, intelligent conversation, and making out



JON I had a casual Friday at work, so I put on a decent outfit.

JACLYN I had such a busy week that I was distracted up until 20 minutes before the date, when I became somewhat nervous.

JON I was mostly calm and pretty excited about the whole thing. I’d never been on a blind date before, and I was definitely looking forward to it. . . . I drove, so I had a terrible time parking.

JACLYN I was five minutes late — oops.

JON I was waiting for maybe about a minute before she showed up.


JACLYN I thought he was very cute, nice eyes, and nicely dressed. [He seemed] both nervous and calm, just like me.

JON She was tall, and she was very well dressed. We were both working through initial meet-up jitters and whatnot. I learned that she is an elementary school teacher and that she just finished grad school last year. The food was delicious, the waiter was perfect. I tried a bit of Jaclyn’s dish.

JACLYN I think what we had in common was that we both are adventurous and enjoy trying and experiencing new [things].

JON We’re both 29, young professionals living in the Boston area. It didn’t seem like we had a whole lot in common. She’s a teacher, I’m an analyst. I’m an adrenaline junkie. I brought up a couple things, like I’m a motorcycle rider and I like to do crazy stuff — she didn’t bite on that.

JACLYN We talked about how we ended up on a Cupid date, what we had done the last couple of weekends, where he lived . . .

JON We didn’t seem like we had much chemistry going on.


JACLYN I just got the feeling we might have been looking for different things.

JON She was good company for the evening and we had a very nice time, [but] I knew pretty quickly, within the first few minutes of meeting, that we didn’t have any sort of chemistry. It seemed clear neither one of us was looking to extend the evening.

JACLYN We said our goodbyes, it was nice meeting each other, gave each other a hug, and we went our separate ways.





JON Because I didn’t feel any particular connection with Jaclyn, I knew early on that we probably were not going to go on a second date.

JACLYN We didn’t make plans.  — Compiled by Jessica Teich

GO ON A BLIND DATE. WE’LL PICK UP THE TAB. Fill out an application at boston.com/cupid.