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2nd Prd 17:51

Dinner With Cupid

Working the date

They’re both business-minded. But can these two suits make a deal?

JAKE DUFFY > 30

Fund operations manager

Continue reading below

HIS EXES WOULD COMPLAIN I work too much or too late.

WHO PLAYS HIM IN A MOVIE A less-tall Vince Vaughn

WHAT VISITORS TO HIS HOME FIRST NOTICE Its cleanliness.

KARYN WATTS > 30

Corporate recruiter

HER EXES WOULD COMPLAIN I tend to overanalyze things.

WHO PLAYS HER IN A MOVIE Jennifer Aniston — she’s funny and goofy and not afraid to laugh at herself

7:30 P.M. TRATTORIA SAN PIETRO, NORWELL

> OPENING TALKS

KARYN I was actually a few minutes late, only because there was construction going on outside the restaurant. I tried to take a pic of it so he would know it wasn’t my fault, but I got nervous when a cop saw me using my phone. I ended up with a pic of my dashboard instead.

JAKE I went straight from work. Before she arrived, I went to the bar for a beer.

KARYN I mentioned the reservation when I walked in. The waitress was a girl who went to my high school, which made things a little easier. She directed me to the table, where he had already sat down.

> LET’S NEGOTIATE

JAKE I thought she was very pretty and had a great smile.

KARYN I thought he was cute. He looked my age and like a business professional, but not too corporate-stuffy.

JAKE She was pretty calm; we had no problem jumping into a conversation.

KARYN The waitress had to come back a couple of times to ask what we wanted to order, we were so busy chatting.

JAKE We grew up in neighboring towns, but we tried not to play the name game too much.

KARYN We talked about our histories. We seem to be in kind of the same boat at this stage of life, in terms of what’s going on with our circles of friends.

JAKE There was never any shortage of conversation. We have a lot of similarities: Our parents had similar professions, we both love boating, and we have both spent a lot of time at a beach called “The Spit.”

KARYN Both of us work in the corporate world and are career-oriented. But it seems like we both enjoy going out with friends and having a good time, too.

 > SHAKE ON IT

JAKE This was kind of random: A large party seated behind us was leaving, and the mother turned on her way out to comment on how great we looked together. It was one of the many things we found a reason to toast to during dinner.

KARYN Clearly she didn’t realize this was a blind date! We kind of awkwardly laughed — but it was kind of cool at the same time.

 > POST-MORTEM

JAKE A-

KARYN A

> SECOND DATE?

JAKE I think we will. We were both surprised at how well we got along.

KARYN I think so. We have already been texting about setting something up. — Compiled by Peter Cocchia

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

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