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Dinner With Cupid

Coin toss

Will a shy guy and a girly girl flip over each other?

Dan Rollo and Val Nesterovskaya.


Vice president of a limousine company

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HIS INTERESTS I am a big Boston sports fan. I like brainless sitcoms [and] can listen to just about any music.

WHAT DROVE HIS EXES CRAZY I’m not around enough.


Speech therapist

HER INTERESTS I love to have intelligent conversation. I watch very silly shows on Bravo.

WHAT DROVE HER EXES CRAZY My compulsive organizing



DAN I really didn’t do much to prepare. I worked earlier in the day, so I took a quick shower and shaved, ironed a shirt, tried to look my best.

VAL I showered, picked out my outfit, did my hair and makeup, and ordered a cab.

DAN I was a little nervous once I got close to the place.

VAL I was calm and optimistic [and] also very curious to meet this person!


DAN She was actually waiting when I arrived. I was a couple of minutes late due to the lack of easy parking in Cambridge.

VAL I was standing by the entrance, trying not to look awkward. He came in and approached the hostess. I kind of figured it was him, so I [went] up and introduced myself.

DAN I thought she was very pretty . . . and dressed nicely. She wasn’t much shorter than me, which is a good thing.

VAL He struck me as just an average-looking guy.


DAN Before ordering drinks we talked about what [we both] like to drink and [the] types of food we like.

VAL I found out that he owns a limo company in Saugus. I also learned a little about his family and background.

DAN I discovered that she was originally from New York before going to BU and obtaining her master’s.

VAL He told me that he would let me “take the reins” on ordering. Usually I like a guy to take control, but in this case I didn’t mind ordering because it seemed like he didn’t really have a good grasp of the menu.

DAN I like sushi, but rather than having her not like something I ordered, I let her choose what she likes best.


VAL I felt pretty comfortable [with Dan]. I grew a little uncomfortable toward the end, though, because I had to think about how I would politely let him know that I was not interested.

DAN I felt a little awkward. I’m a little shy when I first meet people, and I felt I was pressing to keep the awkward silence to a minimum, asking a lot of questions. She either wasn’t interested in what I had to say or she was nervous.

VAL We had very little in common except that I grew up in Queens and he kind of grew up in Queens.

DAN We’re quite opposite.





VAL Definitely not.

DAN She didn’t seem interested, so I didn’t even bother asking her for her number. — Compiled by Peter Cocchia




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