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Dinner with Cupid

Blind date: ‘I honestly thought to myself, “Wow, this girl is way out of my league”’

Will things be looking up for this elevator company employee?

Sean Byrne and Jess Page.
Sean Byrne and Jess Page.

SEAN BYRNE: 27 / office worker

His perfect mate: She would own a brewery

Last thing he read: News stories from Reddit

JESS PAGE: 23 / tour consultant

Her perfect Saturday: Head to a tavern to watch the Red Sox and spend the afternoon outside sipping a beer

Her interests: Cooking, singing, Boston sports



Sean I like to talk a big game, but when it got down to it I was nervous for sure.

Jess Everyone at work knew what was going on. We went through worst-case scenarios and best-case scenarios. I got ready in my work bathroom. I know, weird.


Sean They sat me down at the end of the restaurant. Since I was in the way back, I knew my date was arriving when she just kept walking toward me. She was absolutely gorgeous and definitely my type. She had that type of smile that would light up a room.

Jess Dark hair and dark eyes. Good build, arms covered in tattoos.

Sean I was attracted to her from the moment I saw her. I honestly thought to myself, Wow, this girl is way out of my league.

Jess He seemed really nervous. We gave each other an awkward hug and sat down next to each other.


Sean She had a nice, easy-going personality. She was sarcastic and funny, which is something I look for in a girl. We talked about tattoos, drinks, what we like to do for fun. There was never a stoppage in conversation.

Jess We talked a little bit about how funny it was that we did this. I asked him why he decided to go on this blind date and he told me his friends made him apply.

Sean One of the things we had in common is that we are both huge Red Sox fans.

Jess We talked a lot about what he did for a living, working in a shop for an elevator company. He seems to be pretty close with his family. Then we began to exchange funny first date stories. He definitely had some brutal first dates. Overall, a lot of what we talked about was surface level.


Sean I ordered the rigatoni Bolognese. They usually say nothing can beat your mom’s cooking, but in this case they might be wrong because it was excellent.

Jess I ordered a glass of wine, he ordered a beer. We decided on calamari to split and I had risotto. Really yummy!

Sean For me there were no deal breakers. She seemed quite genuine.

Jess I felt like it was more of an interview rather than a date. I drove the conversation, asked a million questions, and he barely asked anything about me.


Sean We did not do anything after the meal.

Jess Pretty much after the first little bit of our conversation, I knew it wasn’t going to work. We just never really broke surface-level conversation and he didn’t make me laugh.

Sean After the date, I walked her to the train station.

Jess He wanted to get more drinks but I had to head home. We exchanged numbers and hugged good night.


Sean I would if she was interested.

Jess No. He was a really nice guy, we just didn’t connect.


Sean / A+

Jess / B-

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