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Dinner with Cupid

Blind date: ‘My initial reaction was, “I’m going out with a hippie” ’

This inquisitive pair was determined to figure out why they were matched.

Brennah Gladwill and Sky Segal-Wright.
Brennah Gladwill and Sky Segal-Wright.

SKY SEGAL-WRIGHT: 23 / after-school teacher

His interests: Volleyball, biking, soccer

When he is happiest: With friends, writing, or in the woods

BRENNAH GLADWILL: 23 / marketing coordinator

When she is happiest: At the beach with friends playing volleyball

Her perfect date: A picnic



Brennah Only knowing that this guy’s name was Sky, my initial reaction was, “I’m going out with a hippie.”

Sky My aunts told me about it. We agreed it would be a fun experiment.

Brennah We were both on time, which I appreciated. When I first saw him walk in, I thought, Oh thank God, he’s taller than me. Being 6 feet tall myself, it doesn’t always happen.


Sky They led me to the table where Brennah was waiting. I thought she was very pretty and a few years older than me. Her shirt, hair, and earrings made her appear very put together.


Brennah Once we started talking, we never really stopped. Our first topic of conversation was simply trying to figure out why we were a match. So we asked rapid-fire questions back and forth trying to figure it out.

Sky We both like and play sports, read books, enjoy traveling, and think astrology is a waste of time.

Brennah We are both adventurous when it comes to life, food, and trying new things. We share a love of music, and both played volleyball.

Sky Brennah is from Sacramento, and works in marketing. The Kings will be her basketball team ‘til she dies, but for baseball was raised a Red Sox fan.

Brennah We talked about what we would do for a living if money wasn’t an option. I’d be a window display decorator and he would be a writer, so I discovered we both had a creative trait.

Sky We got sushi to start, hot sake, then a spicy hot pot with beef, veggies, and rice noodles. The sushi was my favorite, we should have gotten more.


Brennah We got a hot pot since we saw the people next to us eating one and it looked like quite the experience.

Sky I was having a good time. We seemed to be on the same page when dinner was winding down about moving on to a bar.


Brennah He asked if I’d like to grab a drink after and I said yes. I wasn’t done getting to know him/figuring out why we were a match. We both kept asking each other questions to try to get to know each other better. I felt like I was speed dating.

Sky I got a pretty good picture of who she was. Although, I was surprised by pictures she showed me of her woodworking. I thought it was really cool.

Brennah We ended up walking around Boston Common and had a drink at Beantown Pub.

Sky We exchanged numbers and hugged. It’s what felt appropriate.


Brennah Only time will tell.

Sky I’d go out again, sometimes chemistry takes time to develop.


Brennah / B+

Sky / 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.