Dinner With Cupid

Dinner With Cupid: Crash course

His buddies showed up unannounced. Can these daters still find romance?


Senior account executive


WHO PLAYS HER IN A MOVIE Ideally, a brunette Taylor Swift. More realistically, Mila Kunis.

HER PERFECT DATE A fun spot that’s not crazy-loud so we can carry on a conversation followed by drinks

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Physician recruiter

WHAT HE’D BRING TO A DESERT ISLAND House music, Mountain Dew, and a nice lady to enjoy the island sunset with me


WHAT MAKES HIM A GOOD CATCH What doesn’t make me a good catch?



DAVE I wasn’t really nervous. I like to meet new people, so I was pretty intrigued.

SKYE I woke up in New York [that morning], jumped on an Amtrak train, ran home as quickly as I could, changed, and hopped in a cab to Somerville. I felt pretty calm.

DAVE I was 10 minutes early. I was sitting outside, and when she got out of the cab and walked to the restaurant alone, I could kind of tell.

SKYE I thought he was cute. He had a really nice smile and was easy to talk to. He seemed energetic and outgoing, which I like, and obviously [this] makes dates a lot easier.

DAVE She was good-looking. As far as blind dates go, she was very, very comfortable. We talked about work a good amount [because] we’re both career-motivated. I found out she lives with two people she didn’t grow up with, which is different from me. I live with two of my best friends I’ve known my whole life.


SKYE We have very similar personalities, and our groups of friends are both really funny — something funny happened during the date with his friends, actually.

DAVE We both shared a laugh when one of my roommates came and did a loop through the bar. Come to find out, both of my roommates were there.

SKYE His friends were planning to go out at a bar, and they wanted to check in on how the date was going. That was hilarious and really lightened the mood.


SKYE I wanted to meet his roommates, because I could already tell they’re similar to my guy friends.

DAVE It was funny. Because she’s in a different living situation, I think she was intrigued. I told her I was going out later with my roommates, and she was more than willing [to] come along.

SKYE We had a beer at a bar after. It was close to 10:30, and his roommates were going to go to a different bar with him, but I had been in New York all week and was exhausted. He walked me to the T stop, we hugged. He asked for my number and said, “Talk to you soon.”





DAVE I can see us hanging out again.

SKYE It was a really great date; we had a lot of fun. I think there’s definitely potential.  — Compiled by Jessica Teich

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

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