Dinner with Cupid

Rock-solid romance

Will this jeweler and his date sparkle together?

Ali Adler and Josh Freedman
October 24, 2010

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Ali Adler, 22, Operations associate

Stranded on an island, she’d want: A friend, some great books, and a stocked kitchen

She’s happiest when: With friends and family, and after a delicious meal

Josh Freedman, 24, Chief marketing officer/jeweler

Playing him in the movie version of his life: Paul Rudd

Says he’s a catch because: he’s genuine, a gentleman, a good dresser, and great with parents.

7 p.m. Spice & Rice, Cambridge

A Shore Boy?

Ali: I didn’t really do anything unusual to prepare for the date.

Josh: GTL, duh. No, not really, but I did take a shower.

Ali: I was calm. I’ve been on blind dates before, so I sort of knew what to expect.

Josh: I was pretty relaxed. There was going to be plenty to talk about, since we had never met.

Howdy, Neighbor

Ali: I walked in and he was sitting at the bar near the entrance. I had a feeling it was him, so I introduced myself. I probably would have gone for the handshake, but he greeted me with a hug.

Josh: I think that was the appropriate move; handshakes are too businesslike.

Ali: He was cute. I was glad he was taller than me and dressed nicely. I liked his hair. He seemed mostly calm.

Josh: I went in with low expectations, and I was pleasantly surprised. She was pretty cute. She has really nice eyes.

Ali: I liked that he wanted to share the dishes we ordered. Eating is more enjoyable when it’s a social experience.

Josh: I thought it was really cool that Ali spent the year before college studying in Israel. I’ve been there a couple of times but would love to go back. I mentioned I studied abroad in Barcelona and speak Spanish proficiently, and Ali mentioned she just bought Rosetta Stone for Spanish. I gave her an education about my family’s jewelry business and told her I’d get her a three-carat diamond ring if she plays her cards right.

Ali: We both enjoy traveling, cooking, and food and are interested in politics. We’re also both Jewish, share a love of dogs, and like to exercise. We also have geography in common: We live and work within a mile radius of each other.

Josh: Ali was really friendly and easy to talk to. I thought personality-wise she was a really fun, outgoing person.

Ali: He was an interesting person, and even though there were some awkward pauses, he did a good job keeping the conversation going.


Josh: After dinner, we went to Bukowski’s, down the street.

Ali: After we finished our beers, we left the bar and started walking toward my apartment. He asked for my number, and I gave it to him.

Josh: We had hung out for three hours, which I think is a good amount for a first date. We hugged good night and briefly discussed hanging out again.


Josh says: B+

Ali says: B+

A second Date?

Ali: Josh is a really nice guy and I had a good time with him. I might go out with him again if he asks, but I probably won’t put in the effort to make it happen.

Josh: I’d go out with Ali again. I felt more of a friend vibe, but I don’t believe one date is enough to tell how you feel about someone.

– Compiled by Sarah Mupo

Cupid needs men of all ages: Go on a blind date. We’ll pick up the tab. Apply at

  • October 24, 2010 cover
  • Your Home: Do-it-yourself