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    Dinner With Cupid

    Gone fishin’

    Will these blind daters take the bait?



    Corporate financier


    HE’S HAPPIEST When I’m traveling aimlessly in a foreign country and I have no idea where I am

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    HIS FILM STAR MATE Mila Kunis, as a social entrepreneur

    JENN COLBY > 28

    Marketer and writer

    SHE’S HAPPIEST When I’m with my family or friends


    HER FILM-STAR MATE Ryan Reynolds, as a construction worker


    > HOOK . . . 

    RISHI I didn’t have that much time to get ready because of work.

    JENN I got all dolled up, as usual, after work. In the past two years I’ve been on a bunch of first dates, so I really wasn’t that nervous.

    RISHI I went into it with no expectations. I was just interested in meeting someone.

    > LINE . . . 

    RISHI I couldn’t find the damn restaurant. My GPS was driving me in circles.


    JENN I waited for him at the bar, drinking a glass of wine. After like 10 minutes, I started to get a little nervous.

    RISHI I’d had a glass of wine with friends before I left, so I was glad she was at the bar when I got there. My first impression was that she was attractive [but] not necessarily my type.

    JENN He was dressed really nicely, I thought. And he was handsome. We started chatting as soon as he sat down. He apologized for being late.

    RISHI We talked a lot about traveling, and then work. Coincidentally she works on content production at her job, which I actually need done for my start-up. So she gave me some tips. She seemed like she really wanted to help out.

    JENN I thought it was interesting that he works at GE. Also, he lived in India and he’s traveled all over the world.

    RISHI At one point we were talking about New York City, and we both agreed it was really great. But she was like, “I can see myself living in New York,” and when I asked her if she went there often, she said that she’d only been two or three times. Well, I thought, that’s kind of a big jump.

    JENN We talked mostly about work and traveling. But I remember asking him what he did for fun, and he didn’t really have anything to say — that stuck out in my head. He said he worked on weekends.

    > SINKER?

    RISHI I gave her my card toward the end of the night. I said, “Hey, well, let me know if you ever want to get together in Boston.” And she said she’d check the website, keep tabs.

    JENN He seemed a little buttoned up, reserved. And I’m really outgoing and bubbly. I felt like I was too loosey-goosey for him.


    RISHI B+

    JENN B


    RISHI I didn’t get the feeling she was interested. But I’m OK with that. She lives pretty far away — like 40 minutes from the city.

    JENN Except for a business or marketing thing, I don’t think we’ll be in touch.  — Compiled by Peter Cocchia

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