Dinner with Cupid

Blind Date: ‘We had both binged “Stranger Things 2”’

Her vibe is “a cross between Reese Witherspoon and Barack Obama.” He likes the writing of Isaac Asimov. Winning matchup?

Matt Cassie and Lauren Milione.

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MATT CASSIE: 26 / telecommunications analyst

On a desert island, he’d bring: Golf clubs, Isaac Asimov novels, music collection

What makes him a catch: Being able to make people laugh


LAUREN MILIONE: 25 / special events manager

Who plays her in the movie: A cross between Reese Witherspoon and Barack Obama

First thing people notice in her home: Dead plants



Matt Tinder sucks. The prospect of being set up with someone who seems like a good match for me was compelling.


Lauren My friend who reads the column regularly encouraged me to apply.

Matt I made a mental list of topics for discussion, things that usually lead to good conversation. In my experience: travel, family, and education. I knew the two of us would have a lot in common or we wouldn’t have been matched.

Lauren I had a glass of wine with my roommate. We were jokingly Googling tips for blind dates to kill time.

Matt I got there early to nurse a glass of red wine and watch the Celtics game.

Lauren I showed up right at 8 p.m. and was told my party was already at the bar.


Matt She looked lovely — soft blond hair, pretty eyes, great smile. Cupid is a great wingman. We barely had time to introduce ourselves before the waitress came to take our drink orders.

Lauren He was tallish and casually dressed. He had ordered a glass of red wine. Classy!


Matt I was pleased to learn we share a love of music. We both went to college in upstate New York. We both have experience working for nonprofits. Had we spent more time talking, I’ll bet there were even more common themes.

Lauren We had both binged Stranger Things 2, so that was an easy topic of conversation.

Matt We ordered guacamole to start.

Lauren I ordered enchiladas. He had the filet.

Matt Despite our common interests, we didn’t quite reach the point where polite conversation turns into genuine interest . . .  where you step out of your comfort zone and ask the questions that you’re too embarrassed to bring up when meeting for the first time.

Lauren Even with common experiences, I felt like we weren’t able to get very deep.


Matt If she wanted to stay and talk, I would have. But the bill came in just under $100 so we figured that was a good place to stop. We wished each other well, and to be kind in our exit questionnaires. A rather unceremonious end.

Lauren We hugged goodbye and went our separate ways.

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Matt We didn’t exchange contact info, so it’s unlikely.

Lauren Probably not . But, Boston’s small. It would be funny to run into him.


Matt / B+

Lauren / B


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