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Dinner with Cupid

Blind date: ‘He had a fun shirt on and an impeccable side part’

His friends read Cupid every week and pick teams on Facebook. Will they stand by him as he braves a date himself?

Mike Saccone and Kyle Hemingway.
Mike Saccone and Kyle Hemingway.

MIKE SACCONE: 26 / news writer

His interests: Exercise, yoga, cycling

When he is happiest: Enjoying life with friends

KYLE HEMINGWAY: 30 / creative director

On a desert island, he’d bring: Great music, great company, and an unlimited supply of good gin

Who plays him in the movie: Rosalind Russell



Mike A dear friend who reads Cupid encouraged me to sign up.

Kyle A group of us read it and pick our teams in a super lively Facebook thread (they all better be #TeamKyle this week!).

Mike I went for a run and had a drink on my friend’s roof deck.


Kyle I was nervous. I asked my favorite bartender at Tremont 647 to make me something to take the edge off. She gave me a sassy pep talk, an Aperol spritz, and sent me on my way.

Mike I arrived early and he was already sitting at the bar.

Kyle Pro tip: The bar has a mirror behind it, so you can keep your eye on the front door without looking straight at it.

Mike He had a fun shirt on and an impeccable side part.

Kyle I thought he was handsome and a little nerdy (in a great way). Our waiter welcomed us with a delicious glass of rose bubbles. Mike said he isn’t a wine person, and I joked that he’d get an F for that.


Mike We got the basics out of the way. We both went to Emerson and had mutual friends. He holds a monthly get-together for people to talk art.

Kyle He joked that as someone who investigates people professionally, he was surprised he couldn’t discover anything about me online.

Mike I forget the name of what we ordered, but basically it was a surprise three-course meal.


Kyle We got the chef’s tasting menu, and the kitchen sent out so many incredible dishes. Mike put an entire chunk of Parmesan into his mouth, thinking it was cauliflower. Shocked, he spit it into his napkin. Later, he unfurled his napkin and the cheese fell into his lap.

Mike We joked how he was going to give me an F because I was a hot mess.

Kyle About halfway through dinner, it became clear we’d wind up doing another drink elsewhere. I mentioned that I came over from Tremont 647, so we decided to head back over there.

Mike He was a really nice guy, but just not for me.

Kyle I definitely felt some chemistry. I’ve been on bad dates, and this definitely wasn’t one of them.


Mike We went from Tremont 647 to Eagle and had a drink there. Then we started walking to the train station.

Kyle We both needed to get to the Red Line. . . . Mike diverged from the path we were taking and vanished into the night.

Mike When we got to the train station, he went in and I got into an Uber.

Kyle “Goodbye” was me calling out and trying to figure out where he went.


Mike No.

Kyle I’d be down.


Mike / B

Kyle / Date an A. The goodbye had room for improvement.

GO ON A BLIND DATE. We’ll pick up the tab. Fill out an application at bostonglobe.com/cupid. Follow us on Twitter @dinnerwithcupid.