Dinner with Cupid

Never assume

Is she really thinking what he thinks she’s thinking?

November 8, 2009

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Alison Ring, 28, Communications coordinator

Her perfect Saturday: Early yoga class, a few hours at the beach, cocktails at sunset

Stranded on an island, she’d want: Supply of chocolate, a good book, solar-powered BlackBerry

Matt Avery, 32, Network engineer

Likes: Golf, running, cooking, seeing shows, good beer, being active and amusing

Last book he read: Half Asleep in Frog Pajamas, Tom Robbins

7:30 p.m. Houston’s, Faneuil Hall

Welcome, I’m Matt Alison: I thought Matt was a Houston’s employee because he was dressed very nicely and standing next to the hostess like he was greeting guests.

Matt: She was very cute, nicely put together; class, class, class.

Alison: I like to wear heels, so I thought, “Oh, he’s kind of short.” Sort of disappointing, but not a deal breaker.

Will the Real Alison . . . Alison: The hostess left our order sheet on the table, and they’d misspelled my name. Matt said he was concerned I wasn’t really the girl he was supposed to meet from “the Globe thing.”

Matt: It was definitely awkward. I was really wanting a drink to take the edge off. I felt like she was totally unimpressed. I tried jokes, but she wasn’t having any of it.

Alison: He seemed very nervous.

Matt: At first she was standoffish, but after some wine, she started to open up.

Alison: He recently became a vegetarian to try to reduce his carbon footprint, which I thought was pretty cool.

Matt: I tried to impress her with my quest-to-save-humanity spiel, but I’m pretty sure she saw right through it.

Alison: Our conversation never stalled, and I felt like we had a lot to talk about. But it seemed like Matt never really relaxed. He was very funny, though, but I don’t know if the jokes were a defense mechanism of some sort.

Matt: She’s headed off to grad school. Also, she went to college in LA, and she thinks Jessica Biel’s career is going to turn around any time now. I remember her saying something about JT being on the market again, which is great news.

Alison: Matt said he doesn’t think one person really has the ability to make a difference. I’m a realist, but I do believe that one person, with the right support, can make a positive change.

Matt: I kinda felt like I was fighting an uphill battle the whole night. At first, I was like “out of my league,” but I hung in there -- I’m such a fighter.

Alison: I love Houston’s, so I really enjoyed the meal, and Matt’s great sense of humor kept me laughing.

Compliment or Kiss-Off? Matt: When we left, she gave me the kiss of death: “You’re a really funny guy.” I’m becoming quite the expert in knowing when women aren’t interested.

Alison: He wished me “Good luck in life,” and we waved goodbye. No hug or kiss.

Matt: I kept looking for an in to get her number, but I didn’t want to get rejected, so I was “Umm, OK. Well, so you’re just going home?” I finally let her go on her way after pleading with her not to bash me too bad in the article.

Post-Mortem Matt says: B+

Alison says: B-

A second date? No contact info exchanged.

GO ON A BLIND DATE. WE’LL PICK UP THE TAB. To apply for Dinner With Cupid, fill out an application at

  • November 8, 2009 cover
  • november 8 globe magazine cover
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