Dinner With Cupid

A valiant attempt

Will his romantic advances pay off?

May 15, 2011

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Andrew Sherman, 23, financial data analyst

The last thing he read and enjoyed: Harry Markopolos’s book about Madoff [No One Would Listen]

Who would play him in the movie of his life: Pierce Brosnan

Molly Somers, 22, graphic design grad student

First thing people notice in her home: the cozy atmosphere – fireplace and bookshelves

Recently read Falconer by John Cheever

7 p.m. Vlora Restaurant, Back Bay

Appetite for risk

Molly: I was calm. There is no reason to be nervous if you have nothing to lose.

Andrew: I was pretty calm, more so than usual.

Molly: I was in the city for the day, so I didn’t really do anything to prepare. I ironed my shirt in the morning.

Andrew: I was there first; waited on the couches. There was hardly anyone there, so I knew it was her when she came in. She was attractive – tall, brunette, thin.

Molly: He is handsome and tall, well dressed, not exactly my type physically.

Going for broke

Andrew: We talked about jobs, aspirations, family, European travel experiences, friends’ relationships and stories about those, a little of her own personal relationships, and artsy things that I had no idea about previously.

Molly: Andrew likes to travel and often reads, and his favorite band is Dave Matthews.

Andrew: I think within the first few minutes I had the sense that she would be cool to hang out with. I haven’t met too many girls like her – artsy, sort of sophisticated but not pretentious, outgoing but still a little reserved.

Molly: We have nothing in common. We have both been to Italy. . . .

Andrew: The fact that we were both there indicates similar personalities, because we were willing to go meet some random person with nothing to lose but something to gain.

Molly: Andrew is not my type, and though I am open-minded, the conversation did not reveal anything desirable about his personality. He was very nice and smart, but I don’t know enough about him to like or dislike him. I think we were both cautious about the conversation.

Andrew: I attempted to kiss her in the hallway near the bathrooms, a “valiant attempt,” as described by her.

Molly: A valiant attempt, though unwarranted. It is awkward to deny someone and then continue a normal conversation.

Cutting your losses

Andrew: We didn’t do anything after the meal, although that would have been a good idea.

Molly: We finished our dessert and had the waitress take our picture. I gave him my number but did not expect a call.

Andrew: We hopped on the Green Line together; I got off first.

Molly: We had an awkward side hug on the T. We went our separate ways.


Andrew: A

Molly: B

A second date?

Andrew: It’s certainly possible, for all the reasons I said above.

Molly: Andrew is a really nice guy and I would spend more time with him as a social acquaintance, but nothing more. I would love to set him up with one of my friends.

– Compiled by Maria Oliver

Go on a blind date. We’ll pick up the tab. Fill out an application at

  • May 15, 2011 cover
  • May 15, 2011 cover
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