Dinner With Cupid

Facebook fated

Will these online 'friends' connect in real life?

June 19, 2011

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Rebecca Winik, 35, event marketer

What makes her a catch? Her long, sexy legs

When is she happiest? When she meets someone and feels like she’s known them forever

Mitch Pomerance, 38, financial adviser

What makes him a catch? Beautiful soul and mind

When is he happiest? When he hears his mom laugh

7:30 p.m. Nebo, North End

Signing on

Rebecca: I squeezed in a mani/pedi after work, then ran home to freshen up.

Mitch: I didn’t prepare much. I did call my sister to ask if I should tuck my shirt in or leave it out. She told me leave it out.

Rebecca: I waited a lot longer for a cab than I planned, so I called the restaurant and asked them to let Mitch know.

Mitch: I arrived a few minutes early. The hostess seated me near the window so I could see her come in. When she got out of the cab, my jaw dropped.

Rebecca: I recognized him right away. We are actually friends on Facebook even though we had never officially met.

But will they click?

Mitch: I find Rebecca really attractive. She had a nice smile, long brown hair, brown eyes, and cool earrings.

Rebecca: I thought that Mitch was attractive, and I liked that he was tall. He let me know that he had friended me because he had seen my picture and thought I was attractive, which was very flattering. I liked that he was honest.

Mitch: It was good that a blind date got us together. I [might] never have gone out with Rebecca had her cab not pulled in front of the restaurant.

Rebecca: Mitch grew up in the South and moved back to Boston over a year ago. He works in the financial industry and is writing a book for people to better plan for the CFA exam, which I thought was really impressive.

Mitch: We talked about typical first-date stuff: favorite foods, activities, friends, recent movies. We both have a fear of heights and the invention of the ski lift is why neither of us will go skiing.

Rebecca: We agreed that if there were a rope tow for a black-diamond trail, we’d be great skiers.

Status update

Mitch: I definitely got more comfortable as the night wore on and I had a couple glasses of wine. First dates are hard!

Rebecca: I was worried that he was really nervous. I tried to make him at ease. At one point I went to the restroom, and when I got back, he told me I should give him a second chance, given how awkward the situation was. I thought it took guts to say that, and I agreed to see him again.

Mitch:She told me she would go out with me again as long as I didn’t take her to an audience-participation comedy show.

Rebecca: After, Mitch seemed to become a lot more at ease. He made me laugh out loud several times. He joked that I should change my status on Facebook to “In a Relationship” with Mitch. After dinner we decided to share a cab, since he lived on my way home.

Mitch: I got her number. We hugged in the cab and I jumped out.


Rebecca: B+


A second date?

Rebecca: We talked about getting together again in a week or so. At the very least, I see us becoming friends.

Mitch: Yes, I think that would be fun.

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

  • June 19, 2011 cover
  • June 19, 2011 cover
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