Dinner with Cupid

A tall tale

Above average in height, will they see eye to eye?

February 28, 2010

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Kevin Rivera, 25, Comparison-shopping strategist

Says he’s a catch because: He’s creative and loves to explore new things.

Comedian he most relates to: Sarah Silverman, but a little less crude

Phil Pitt, 24, Nonprofit programming manager

His perfect date: Meandering around the city, ending up at a Mexican restaurant

Comedian he most relates to: Sarah Silverman, but not as crude

7:30 p.m. Pops, South end

Looking Up Kevin: I was a little nervous, but kept telling myself: “You get a free meal. What’s the worst that could happen?”

Phil: I’ve had blind dates, but I’ve always known something about the person. This was truly a blind date. But I made myself go in with an open mind.

Kevin: The host introduced us -- it’s a small space, so I heard Phil say my name when he came in.

Phil: I thought he was quite handsome, well dressed, and even taller than I am, which never happens. A big plus.

Kevin: I thought he was very cute. He’s tall like me and has a great smile.

Missing Bob Barker Phil: When we were being led to our table I was thinking he could be a bit shy, but right away that changed.

Kevin: After a few minutes I think we were both feeling pretty comfortable.

Phil: Right away we bonded over the fact that we’re both quite tall, and prefer men who are also tall. We also discussed how we had come across Dinner With Cupid. I had applied on a whim, and he was convinced to apply by his female co-workers.

Kevin: We talked about the fact that we might be the first gay setup in Cupid.

Phil: The staff was really nice and knew about the blind date. I could tell they were looking to see how it was going.

Kevin: The food was fantastic and the service was absolutely perfect.

Phil: We discussed family life, our jobs, college, relationships with friends.

Kevin: We talked about how we both came out of the closet.

Phil: I learned Kevin is half Puerto Rican and works in advertising. I also learned his apartment burned down last year, so he had to move. We discussed the importance of renter’s insurance, which pretty much covered everything for him.

Kevin: We agreed The Price Is Right is just not the same without Bob Barker.

Phil: We bonded over the fact that we’re both always hungry. I love to eat, and he likes to cook.

Kevin: It wasn’t until later in the night that I noticed his cute dimples.

Phil: I really like the name Kevin. I can’t say it without thinking of the mom in Home Alone screaming “KEVIN” on the plane, realizing they’ve left him at home.

Double Hug Kevin: After dinner we just stayed and finished our drinks and chatted a bit.

Phil: All in all we were at the restaurant for well over two hours.

Kevin: He walked me to my car, which I thought was a nice gesture. We exchanged numbers and hugged. Twice.

Post-Mortem Kevin says: A

Phil says: A

A second date? Already in the works.

ATTENTION GAY AND LESBIAN SINGLES: CUPID NEEDS YOU. Go on a blind date. We’ll pick up the tab. Fill out an application at

  • February 28, 2010 cover
  • february 28 globe magazine cover
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