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Dinner with Cupid

Blind date: ‘I asked about her dating history, and that filled most of our meal’

Will talk about their exes haunt this date?

David Gabriel and Max Dinerstein.
David Gabriel and Max Dinerstein.

DAVID GABRIEL: 28 / law student

Last thing he read: Bon Appetit magazine — he loves to cook

What makes him a catch: He is committed, intentional, and hardworking

MAX DINERSTEIN: 25 / floor leader for cosmetics retailer

Her interests: Cooking competition shows

What makes her a catch: She’s a good cook, super supportive, and loves to help people



David I got to the North End early. I had a cocktail, then got to the restaurant.

Max I did basically nothing to prepare because I believe in setting realistic expectations. The waiter brought me to David. He was not my type.


David I wasn’t attracted physically. She insisted on needing to read over the whole menu before we talked. I thought that was cute.

Max David mentioned that he was a bartender and I wanted to talk about that, but he interrupted me to ask what “my story” was. We figured out what to order and I dived into my whole life story.


David She told me what foods she liked and didn’t, and why Bostonians love lobster and beer so much.

Max We decided to split puttanesca because I wanted to see how $21 puttanesca compared to mine, which is approximately $6 for ingredients. Mine was better. I ordered a sauvignon blanc, because I know that wine pairs well with pasta (further proving how good I would be as a bartender).

David We had cannoli for dessert. Service was great.

Max The waiter visited a little more than was necessary, but he probably had nothing else to do.

David I asked about her dating history, and that filled most of our meal. We both had ex-partners that had ghosted us. Her philosophy on dating was definitely a red flag. She didn’t think about life or partners in a consequential way. Everything seemed to be about the here and now and not what it will mean in five years.


Max We literally spent the whole time talking about exes, not exactly sexy.

David I don’t know if any of my impressions are even true! She was a good person. Just a little too unmotivated for my taste.

Max As soon as we finished dessert, I opted to figure out a polite way to go.


David From my vantage point, she wasn’t any more interested in me than I her.

Max David headed to the bathroom, and I thought about just leaving but figured that was Not Nice, and also he had done nothing wrong besides spending the whole date talking about exes.

David She asked if I wanted to walk to the Haymarket station together.

Max We hugged after I awkwardly asked, “Should we hug?”


David Probably not.

Max Absolutely not.


David / C+

Max / C-

Readers: Check BostonGlobe.com on Valentine’s Day, when we’ll have a story about Dinner With Cupid’s 10th anniversary. To celebrate, we gathered some of the brave souls who trusted us to set them up on blind dates.

Go on a blind date. We’ll pick up the tab. Fill out an application at bostonglobe.com/cupid. Follow us on Twitter @dinnerwithcupid.