Dinner With Cupid

Candid camera

Will this photographer click with his fashion plate date?

July 17, 2011

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Ryan Richardson, 25, wedding photographer

What he’d need on a desert island: his camera, a radio, and a book on how to train the perfect monkey butler

His ideal mate: would teach art history by day and by night would foil art heists at museums

Emily Cash, 26, Nordstrom stylist

What she’d need on a desert island: ravioli, a corkscrew, and a fierce pair of shoes

Her ideal mate: funny guys who aren’t afraid to be themselves but also have a sense of style

7:30 p.m. Hungry Mother, Cambridge

Picture perfect

Ryan: I probably went through three or four different ensembles, trying to figure out the subtext of each. I downed an iced coffee on the drive up, which maybe wasn’t the best idea.

Emily: I was on time, and he was a half-hour late. To be fair, I live three blocks away and he was commuting at rush hour on a miserably rainy day.

Ryan: I blame the rain and my poor sense of direction. I had to keep circling the block for parking. I was a little bit wet when I stepped in. I suppose I had that little lost deer look.

Emily: He wasn’t really my type. I’m a tall girl who likes to wear tall shoes, so I definitely prefer someone with height.

Ryan: She was pretty. Her outfit was well put together (though it was too dark to go into deep red-carpet analysis).

Emily: I could tell that he felt bad for being late. He apologized several times.

Ryan: I know when I’m waiting for someone that long I can get tense. That’s the great thing about technology, though – even when you’re waiting, you can still be in touch. Or at least play Angry Birds.

Say cheese

Emily: Ryan is trying to break into wedding photography. We both thoroughly enjoy wedding programming on the WE network – like My Fair Wedding, with David Tutera, and Bridezillas.

Ryan: We talked about work, family, and our secret pact to say nice things about each other in the article. We both had shameful interests in reality TV. We also discussed our irrational biases: her suspicion of Connecticut and my distrust of Rhode Island.

Emily: We’re both chatty and could always find something to talk about.

Ryan: I got relaxed as the evening went on. A lot of it was Emily’s influence. She was at ease, and I enjoyed that about her.

Examining the negatives

Emily: He kept making self-deprecating jokes. My life isn’t perfect. I’ve struggled, but he kept [telling] me everything he seemed to be embarrassed with. It made me feel sad and uncomfortable.

Ryan: I wasn’t on top of my game. In the blind date sphere, you’ve got to give them the old razzle-dazzle. I [wasn’t] up to that challenge that evening.

Emily: We did have interesting conversations. It’s not like he threw up or fell off a bar stool (true stories from other dates).

Ryan: She was meeting friends for drinks, and I had to get back to the sad suburbs. I did get to check her out [while] standing, though, which was very nice. I mean that in the least lecherous way.

Emily: We went our separate ways.

Ryan: Unless I get a very strong vibe, I try not to start any kissing. There’s nothing worse than puckering up to someone with a confused look on their face.


Emily: B

Ryan: B+

A second date?

Emily: Nope. There wasn’t any chemistry.

Ryan: Probably not. After a lackluster romantic career like mine, you get pretty good at telling when there’s a mutual connection.

GO ON A BLIND DATE. We’ll pick up the tab. Fill out an application at

  • July 17, 2011 cover
  • July 17, 2011 cover
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