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Dinner with Cupid

Blind date: ‘I was getting nervous that I was getting stood up’

Will these two daters be able to smooth over a nerve-racking start to their dinner?

Phil Black and Caitlin Sherr.
Phil Black and Caitlin Sherr.

PHIL BLACK: 29 / financial analyst

What makes him a catch: He’s humble, easygoing, and empathetic

His perfect mate: A down-to-earth, athletic woman who is passionate about her profession

CAITLIN SHERR: 27 / retail marketing

First thing people notice in her home: Pictures on her wall that she has taken

When she is happiest: Sitting on the beach with the sun shining



Phil My sisters signed me up and I decided to play along.

Caitlin My parents are fans of the column and urged me to sign up.

Phil I got seated at a table by myself. After about 10 minutes, I was getting nervous that I was getting stood up but then someone informed me they had made a mistake and she was already there.


Caitlin I sat at one table at the back of the restaurant and he sat at a table at the front.

Phil It made it nerve-racking but ended up working out well as [it] helped break the ice and gave us something to laugh at.

Caitlin I thought he was really handsome, but what stood out to me was his smile and his laugh.

Phil She had pretty eyes and long blond hair, both pluses for me.

Caitlin As soon as we started talking I knew this was going to be a great night.


Phil She seemed to have a game plan; she was driving the first few questions, which I appreciated as I was just winging it. The waiter came back multiple times but we were entrenched in conversation.

Caitlin I was really impressed with his passion for running and giving back to the community, after learning more about a company he created with one of his sisters that offers online language resources to students.

Phil We talked about everything, from family to where we were from, different places we have lived, grad school, and music. It was a very free-flowing conversation.


Caitlin We are adventurous eaters and were willing to try any type of food. After discovering we both liked Brussels sprouts, I gave my date bonus points.

Phil We agreed it would be fun to order a bunch of tapas. We ordered Brussels sprouts, falafel, pork belly, shishito peppers, and calamari. Everything was delicious but the Brussels stood out.

Caitlin We both liked outdoor activities, from walking around the city to running. While he snowboards and I ski, we both agreed we didn’t love being cold. We found out that we both grew up skiing at the same mountain.

Phil We are both young professionals, enjoy being active, are close with our families, and love Labrador retrievers. I can definitely see why we were matched up. After talking for what felt like a short time — but in reality was a couple of hours — it seemed like we were connecting.

Caitlin It actually sort of felt like we had met before. I was secretly dreading the night ending.


Phil We did not do anything after [dinner] as it was getting late.

Caitlin After my date graciously offered to pay, we settled the check and headed out.

Phil The date ended by exchanging numbers and agreeing that we would have to get together again.

Caitlin We hugged goodbye.


Phil I think we will, I look forward to getting to know [her] better.


Caitlin I would be interested.


Phil / A-

Caitlin / A

Go on a blind date. We’ll pick up the tab. Fill out an application at bostonglobe.com/cupid. Follow us on Twitter @dinnerwithcupid.