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    Dinner With Cupid

    Blind date between two dedicated workers

    Will they find the time for love?


    History teacher

    HIS INTERESTS > My students bring so much happiness and freshness into my life.

    ANY PETS? > Sadly, I don’t have the time.


    HIS PERFECT DATE? > A good conversation trumps anything else.


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    Senior tax analyst

    WHY SHE’S A CATCH > I’m a young, confident, pretty woman with a good job.

    WHO PLAYS HER IN A MOVIE? > Kate Winslet

    WHAT HER EXES HATED > I get really caught up and forget to check my phone for hours.




    BROOKE I had some time after work and before the date, so I got a quick manicure.

    ALEX I spent a half-hour or so wandering the shelves at Brookline Booksmith, my favorite bookstore.

    BROOKE I was pretty calm earlier in the day. As it got closer, friends and family started telling me horror stories about blind dates.

    ALEX I wasn’t really feeling nervous until just before, 6:56, when I suddenly considered the possibility that she might not show up.



    BROOKE Alex had a very warm, friendly smile. He was more attractive than I expected – didn’t want to get my hopes up beforehand.

    ALEX Brooke had long brown hair, and she was dressed very nicely. She’s definitely a pretty girl.

    BROOKE Alex didn’t seem nervous, and he was pretty talkative, which was nice because I can be a little shy. Truthfully, I was just happy that we were having a conversation and that it wasn’t awkward.

    ALEX We talked a little bit about her work and the unseasonably warm weather. We’re both from the Boston area, so we connected a little bit over that.


    ALEX I tend to be pretty extroverted, so I was comfortable more or less right away.

    BROOKE I learned that Alex works in Brookline at a charter school as a teacher. He got an offer to go to Alaska and act, so he was there for six months. He also told me he was on Jeopardy, which I’m a huge fan of, and now he’s back in Brookline teaching.

    ALEX The conversation was really pleasant, and it was interesting to hear her describe her line of work, which is very different from mine. We talked about how much we love living and working in Boston, though both of us had expected to live elsewhere coming out of college.


    BROOKE We both work a lot. [For part of the year,] I work 80 hours a week and on weekends, and Alex works around the clock teaching and coaching his students. He seems really passionate about his job but doesn’t seem to have time for anything else.

    ALEX She was very polite, but she seemed so neutral about the whole thing. I think I knew within the first few minutes that there was nothing between us.

    BROOKE Alex said he needed to get back to his place to grade papers, so we ended dinner around 9. It was kind of disappointing and a sign that he didn’t really have free time.

    ALEX She seemed like she wanted to get the whole thing over with.



    ALEX C


    BROOKE I think it would be hard to find the time to date again.

    ALEX I don’t think we’d be interested.

    – Compiled by Erica ThompsonGO ON A BLIND DATE. We’ll pick up the tab. To apply for Dinner With Cupid, fill out an application at