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The Boston Globe

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Dinner with Cupid

Blind date: Love me do

Will these two musical types find out they’re in tune?

From left, Derrick Flanagin and Sasha Pedro.

From left, Derrick Flanagin and Sasha Pedro.

DERRICK FLANAGIN

28 / Musician and Chef

HIS PERFECT DATE

One that involves very little planning

FIRST THING VISITORS TO HIS HOME NOTICE

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The insane urban garden we have in our front lawn

SASHA PEDRO

25 / Guitar Teacher

HER PERFECT DATE

Hikes, roller coaster rides, Mexican food, and dancing

WHEN SHE’S HAPPIEST

When life is simple, usually outside

7:30 Bella Luna, Jamaica Plain

> TUNING UP

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DERRICK One of my co-workers told me he’d been on “less than 100” blind dates via Tinder and OkCupid, and he assured me it was going to be a great time.

SASHA I was expecting to be nervous, but hey, turns out I wasn’t.

DERRICK Before the date I had to bike 6 miles from the Seaport to my house, then it was another 5-mile ride to the restaurant.

SASHA I spent most of the day preparing for a trip the next day, not much time to prepare for the date. 

DERRICK I’m pretty sure I got there at 7:30 on the dot, but she was already there.

SASHA Our table was outside, not a bad place to wait.

> STRUMMING ALONG

DERRICK I was glad she wasn’t basic.

SASHA I saw the host walking with a guy wearing jean cutoffs who had clearly just ridden his bike to the restaurant. One of those “and I just knew he was my date” moments. 

DERRICK The host . . . pointed me to the right table. It was much more painless than I had anticipated.

SASHA I smoothly opened with “So, uh, how was your day?” and he had a pretty interesting day, so conversation flowed from there. . . . We had broad things in common — music, travels, etc. We both had friends whose Dinner With Cupid dates had bombed.

DERRICK It seemed like we were pretty similar: We’re both musicians, we both like traveling. We basically spent the dinner talking about those things.

SASHA I mentioned a little about my upcoming trip and found out he has been all over the place. We talked about our favorite travels.

DERRICK The food pretty much fell by the wayside because we were having a pretty good conversation, and the beer seemed more of a priority.

SASHA He used “oligarchy” in a sentence. Swoon.

DERRICK There may have been some sparks.

> UNPLUGGED

SASHA There was an open mic comedy night going on inside. We overheard it and eventually went in to see it.

DERRICK I was pretty excited about it.

SASHA I got worked into a comedian’s joke. That was fun. . . . We were there till 11. Crazy. [Eventually] I walked with him to his bike, he walked with me to my car. I gave him my number.

DERRICK We shared a hug.

SASHA We hugged and I thanked him for a nice time. He bid me a safe trip.

> SECOND DATE?

DERRICK Yeah. I texted her just now and told her I was having trouble with this question, so we sorted it out.

SASHA I’d be game. 

> POST MORTEM

DERRICK B+

SASHA A

GO ON A BLIND DATE. WE’LL PICK UP THE TAB. Fill out an application at bostonglobe.com/cupid.

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