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Dinner with Cupid

Blind date: ‘I was sad to see her go’

Will their shared experience as educators bond these daters?

Leif Jacobson and Rosie Levenson.
Leif Jacobson and Rosie Levenson.

LEIF JACOBSON: 29 / teacher

His interests: Golf, travel, politics

His perfect mate: Alexandria Ocasio-Cortez, doing something about social justice

ROSIE LEVENSON: 26 / donor relations officer

Her perfect Saturday: Coffee in bed, hiking, brewery, jazz bar

Her perfect mate: Channing Tatum, leader of a charter school



Leif I didn’t have too much time to dwell on the evening. I did manage to fit in a quick run beforehand.

Rosie I went for a run earlier and had a pep talk with my driver on the way there.

Leif I couldn’t find parking and showed up five minutes late. Facepalm.


Rosie He was very apologetic when he arrived, which definitely helped his cause.

Leif I was immediately struck by her beauty. I noticed her confident and welcoming smile — that put me at ease.

Rosie The first thing I noticed was his big smile. Immediately I felt more comfortable around him.


Leif We started with the obvious topic of how we both ended up there, which allowed us to quickly identify common experiences. When we discovered that she had done City Year and I had done Teach For America, that opened the conversational floodgates.

Rosie We chatted about the similarities and differences in our experiences. We spent a lot of time talking about the importance of doing service-oriented work. Someone with an AmeriCorps background is usually a really good indicator [of] a genuinely good person who cares about the world.

Leif We were bonded by similar values, which felt nice. Our conversation ranged from more easygoing topics — comparing exercise routines, for example — to deeper conversations about challenges in how we’ve evolved over time. We found connection in how we organize our lives — finding meaning in the little things.

Rosie We ordered a dozen East Coast oysters, Alaskan king crab (to die for!), and lobster and corn bisque. The food exceeded all of my expectations.


Leif I so appreciated her willingness to “go for it.” We ended up ordering crab legs for two, which were delicious. Toward the end, we both sensed that we were attracted to one another, which was flirty and fun.

Rosie No problem sharing dishes and getting a little messy.


Leif We have different personality styles, but I didn’t find that was pushing me away. Initially, she had a certain intensity but I came to recognize it as irreverence.

Rosie I did feel more comfortable to crack witty jokes or bad puns as the night went on. We went to The Beehive after for more cocktails and to listen to jazz. Around 11:30 or so we both realized we were getting tired and headed out.

Leif We walked back to my car and shared a hug and kiss goodbye. I was sad to see her go.

Rosie I had a great time. We spent almost five hours together.


Leif Yes, I think that we should go out again.

Rosie For sure, we agreed. He lives near the Arboretum and I am a tour guide there, so lots of potential to see fall foliage together.


Leif / A-

Rosie / 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.