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Blind date: ‘I asked him his age and he said 23, and I gasped and started laughing’

Will a typo in a Cupid application lead to a match despite an unexpected age gap?

This week's daters: Caroline and ShayanHandout images

CAROLINE R.: 34 / senior manager, investor relations

WHEN SHE IS HAPPIEST: Skiing, biking

WHAT MAKES HER A CATCH? She’s thoughtful, kind, and generous.

SHAYAN O.: 23 / associate scientist

WHAT MAKES HIM A CATCH? He’s empathetic, a good listener, and an overall positive person.

HIS HOBBIES: From soccer and squash to rock climbing and marathon running



Caroline I didn’t really prepare for the date. I had been working until an hour before, so I just changed my clothes and refreshed my makeup.

Shayan I came from work. I was a little nervous, but I’m a pretty outgoing person. She was already there. I said hi, and gave her a hug.


Caroline I was sitting at the bar and he came up next to me. I thought he was cute.

Shayan I thought she was cute. We both ordered a glass of wine — I got malbec and she got pinot noir. We got to talking right away.


Caroline I discovered pretty quickly that he was significantly younger than me. My first clue was how he described his job. He described it in very general terms as “I do research at a biotech company,” and moved on. And I thought that was odd as I usually give a little more detail.

Shayan I mentioned how I had just graduated and was considering grad school in the next few years, which prompted her to ask how old I was.

Caroline I was surprised that someone in his 30s would be applying to medical school. I told him it was great that he was going to do that at this time in his life and he told me that it was a pretty normal time to apply to medical school. This is when I realized that we were probably not the same age.


Shayan We quickly learned that there was a mix-up and that Caroline is 11 years older than me.

Caroline I asked him his age and he said 23, and I gasped and started laughing. Thank God I had my wine at that point! He even showed me his license displaying he was born in 1999 (when I was in fifth grade)! [After I stopped laughing,] I was able to tell him that I am 34, and we agreed that it was no longer a date. We decided to stay and have a nice meal as friends.

Shayan We talked about how we both grew up skiing, and I was impressed that Caroline tries to go skiing every weekend. She’s also run a few half-marathons.

Caroline I ordered the Bolognese pasta. It was very good.

Shayan I ordered farfalle al limoncello. Both the service and the food were great.


Caroline Shayan was cute and would be a great match for someone his age.

Shayan She was nice enough to let me pick her brain about working at a biotech investment firm, since it’s something I am potentially interested in.

Caroline Shayan was pleasant to talk to and we were able to have a nice time. I walked home and called several friends to relay the evening.

Shayan We walked out together, said bye, laughed about the mix-up, and walked in separate directions.


Caroline Lol, no second date!

Shayan There won’t be another date. I hope she’s able to do another Cupid date with someone else!



Caroline / We agreed on a rating: B

Shayan / B

Go on an in-person or virtual blind date. We’ll pick up the tab. Fill out an application at bostonglobe.com/cupid. Follow us on Twitter or Instagram @dinnerwithcupid.