Dinner with Cupid

Oh, very young

Seeking fun? Let the millennial generation show you how it’s done.

Davy Fields and Jessica Bilbo. Davy Fields and Jessica Bilbo.
September 20, 2009

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Davy Fields, 23, Product manager

Stranded on an island, he’d want: music, iced coffee, and Google

His perfect Saturday: Drinking beer and watching the Red Sox with friends

Jessica Bilbo, 21, Nursing assistant

She’s a catch because: She can usually make people laugh -- and she can cook.

Her perfect date: Trying out sky-diving, followed by drinks and sushi

7:30 p.m. Cafeteria, Back Bay

Mystery Date Jessica: I was pretty anxious about who was going to show up as my date.

Davy: I didn’t know how it would go down. I’d read a lot of the Cupid columns and knew anything could happen.

Jessica: I arrived a little early because I was trying to avoid game traffic.

Davy: I got there at 7:30 and they told me she wasn’t there yet, so I stood around for about 10 minutes. The hostess asked if my date could be there already, and I said, “Well, yes, I don’t know what she looks like,” which threw the hostess for a loop.

Jessica: I was relieved that he was not the two or three potential Davys that had been milling around the entrance.

Davy: She had pretty eyes and I thought she was cute.

Funny Girl Jessica: He seemed pretty calm, but I think he was about as anxious as I was.

Davy: She seemed very at ease, cool about the whole thing.

Jessica: We had both heard good things about the white sangria, so we ordered that, and it was delicious.

Davy: We talked about the uniqueness of the whole thing, and how it was funny that we had no mutual friends because it was a truly “blind” date.

Jessica: I learned a bit about his job and that he gets to travel a lot, which I envy.

Davy: We talked about where we each went to college and activities we liked to do around the area. The conversation came easily -- no awkward pauses.

Jessica: I think we shared a similar sense of humor. I laughed a lot on the date.

Davy: We had a lot of common experiences to talk about, being two college-aged people in the best college town in the world.

Jessica: He was easy to talk to and laughed at my jokes. I may have gotten more comfortable with each drink.

Davy: I really like a girl who’s funny, and Jess is funny.

The After Party Davy: We went to Boston Beer Works after and continued the night there. That was when I knew we were having a really nice evening for ourselves.

Jessica: After Beer Works, we decided to go to a going-away party for a friend of his. I was excited to see how he interacted with his friends or in a group.

Davy: We spent a long time together afterward, more time than at dinner. After we went to the last bar, it was about 1 a.m.

Jessica: He walked me back to my car.

Davy: There was a good night kiss outside of her car on Newbury Street. We had spent a long time together and had a great time, so I went for it.

Post-Mortem Davy says: A

Jess says: B+

Second date? Already planned, says Davy.

GO ON A BLIND DATE. WE’LL PICK UP THE TAB. To apply for Dinner With Cupid, fill out an application at

  • September 20, 2009 cover
  • september 20 globe magazine cover
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