Dinner With Cupid

Blind date: ‘I appreciated that he was reading on his Kindle’

They share an alma mater, liberal politics, and an interest in law. But are they too much alike?

Sydelle Barreto and Kegan Smith.
Sydelle Barreto and Kegan Smith.

KEGAN SMITH: 27 / school operations administrator

What makes him a catch: He’s loyal, ambitious, and a good cook

His interests: Learning to sail, studying for the LSATs, leans politically to the left

SYDELLE BARRETO: 22 / public policy intern

Her interests: Cooking, writing poetry, politically leftist

Last thing she read: An Indigenous Peoples’ History of the United States



Kegan It was time for a new challenge.

Sydelle It seemed like a way to get out of my comfort zone.

Kegan I got there early to grab a drink and start on a new book. Sydelle was a bit late, but I didn’t stress over it.


Sydelle They brought me to where Kegan was waiting. I appreciated that he wasn’t scrolling through his phone but rather reading on his Kindle.

Kegan Sydelle was attractive, though not my usual type.

Sydelle He seemed really friendly and had a great smile.


Kegan We discovered we both went to Northeastern and studied political science and economics. We had similar views on politics.

Sydelle One of the first topics we broached was our university administration. There’s been a lot of outrage at Northeastern’s contract with [US Immigration and Customs Enforcement] and we discussed how disappointing it was to us as alumni.

Kegan She fenced in high school, a sport I was always interested in. We also discussed past travel; she’d studied abroad in Europe and had a transformative experience.

Sydelle We shared a love of reading. He seemed to have really good tastes. We also were both considering law school.

Kegan I ordered a lobster roll. The roll was good, but nothing spectacular for Boston.

Sydelle I got a sandwich with a green goddess sauce. The service was excellent and the patio was gorgeous with its fairy lights, but my sandwich was incredibly salty.


Kegan She seemed friendly and genuine. But I didn’t find myself more attracted to her. We shared interests, but it felt too comfortable and there was no excitement for me.

Sydelle He was one of those people who laugh easily and often, which put me at ease. We had things in common, but it felt like dinner with a friend.

Kegan She mentioned recently getting out of a relationship and had plans to leave Boston in the near future and neither of these things was ideal.

Sydelle We ran out of topics and it felt a bit awkward.


Kegan I had to be at work early the next day and was happy to end the date.

Sydelle We had a goodnight hug and ordered our separate Ubers home.


Kegan No. Sydelle wasn’t the woman for me.

Sydelle No. He was nice, but there was zero chemistry.


Kegan / B+

Sydelle / B-

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