Dinner with Cupid

Pass or fail

How will two high school teachers grade their own date?

(Photograph from Chris Anderson)
October 18, 2009

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Chris Anderson, 26, Video editor/instructor

Says he’s a catch because: He’s easygoing, smart, trustworthy, and likes to make others happy.

Who plays him in the movie of his life?: “Michael Cera, though I’m not that whiny.”

Holly O’Donohue, 24, Teacher

Her perfect Saturday starts with: Taking her dog for a walk through a nearby marsh

Says she’s a catch because: She’s an athlete and “a pretty big nerd.”

7:30 p.m. Angela’s Coal Fired Pizza, Revere

Go North, Young Man Chris: The restaurant was kind of far away, so I left early to beat the traffic.

Holly: Walking into the restaurant, the manager picked me out almost immediately. “You look nervous as hell!” he said. “I know what you’re here for.” And then he sat me at the table, where Chris already had a beer.

Chris: I was mostly nervous that I wouldn’t be attracted to her and have an awkward dinner. When I saw her,

I was relieved she was attractive and

as nervous as I was.

Holly: I’m incredibly unobservant by

nature but at least noticed that he wears glasses.

Food to Soothe Nerves Chris: She seemed a little nervous at first, but the conversation flowed pretty easily.

Holly: We split a pizza and some wings. Both food and service were very good.

Chris: I wish the restaurant was closer so I could go more often.

Holly: Conversation stayed pretty basic. “What do you do for work/fun?” sort of questions mostly -- although we did share a few laughs about the oddities of our profession and about working with young people.

Chris: Her uncle used to be the chief of police in the town I work in and I’ve seen him many times at meetings. She plays ice hockey.

Holly: Aside from both being teachers, we had little to nothing in common.

Chris: We both work teaching high school. We both have September birthdays. We both have dogs.

Holly: I was more comfortable as the meal went on, but part of that could have been the sangria. I stuck with the “one drink” rule my friends imposed.

Chris: We had no trouble keeping up conversation.

Holly: Chris had a lot of interests that don’t appeal to me. I wouldn’t be shocked if he felt the same about mine. Early in the date when we talked about our interests and almost nothing lined up, I knew it was not going to work out.

Chris: We seemed to get along well. I don’t think anything we said was a deal breaker, except maybe how far away we live from each other.

Doggie Bags Chris: She had to be up early the next day, so we didn’t do anything after dinner. We had our leftover pizza wrapped up, and I walked her to her car. I gave her my number and we hugged goodnight.

Holly: We chatted for a moment in the parking lot before going our separate ways.

Post-Mortem Chris says: A-

Holly says: C+

A Second Date? Chris: I would be interested, but the distance might make it difficult.

Holly: No

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

  • October 18, 2009 cover
  • october 18 globe magazine cover
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