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Dinner with Cupid

Blind date: ‘I showed up early with a vase of flowers’

Do we have a budding romance on our hands?

Jenn Raymond and Kyle Crosby.

KYLE CROSBY: 32 / tech registrar

On a desert island, he’d bring: Whiskey, guitar, and a great companion

When he is happiest: Helping others who have less

JENN RAYMOND: 32 / hairstylist and colorist

Who plays her in the movie: Leslie Mann

Her ideal mate: Tall guys that have technology smarts



Kyle I spent a lot of time planning post-date ideas (a HarborWalk to the North End, etc.). However, in the end I decided to focus more on just trying to help my date have an enjoyable evening.

Jenn I made myself a cocktail and tossed it back.


Kyle I showed up early with a vase of flowers and asked the hostess to put them on our table. I went to the bar to have a pre-drink. I noticed a tall girl with beautiful wavy hair. When I saw her turn around, I have to admit I was excited. I’m a sucker for a woman who takes the time to dress up for an evening out.

Jenn Ooh, he’s tall. Nice! was my first thought. His face lit up a little when he saw me.


Kyle We immediately hit it off, so we skipped the typical first-date questions and started chatting.

Jenn He’s multilingual and he’s lived in a lot of places and seen a lot of the world, which I thought was very interesting.

Kyle We ordered burrata with prosciutto for the appetizer. It was her first time having burrata and she loved it. For her main course she ordered pappardelle alla bolognese. Since I lived in Italy for five years, she asked me to help her with the pronunciation; she actually did a great job!

Jenn He ordered in Italian and then I think he switched to Portuguese [for] our waitress. Which was pretty impressive.


Kyle I think the most romantic moment was just as we were about to leave. I asked if she wanted to take the flowers home with her. Up until then, she had thought that the flowers were just part of the restaurant decor.

Jenn I kind of looked confused and said, “I don’t know if they’d like that” and then he said, “No, I brought it for you!” And then I really looked, and it was a hyacinth plant in a special vase to keep the roots and the bulb separate. It was beautiful.

Kyle She was clearly taken aback, but touched.

Jenn He was so sweet to have gotten something plantable and renewable, and he even knew the background of why the plant is named hyacinth (Greek gods; he majored in philosophy).


Kyle I had planned on us walking to the North End to find dessert. It turned out to be too cold, though, and she had to get up early, so I scrapped the idea.

Jenn I would have gone for a drink if I didn’t have to work the next day.

Kyle We called separate Ubers, and while we waited, she leaned her head against my shoulder. I don’t think we said much at that point. We kind of just enjoyed the moment. We hugged goodbye; she kissed me on the cheek.

Jenn That was as romantic as it got.


Kyle We’re already planning a follow-up later this week.

Jenn Sure, why not!?


Kyle / Definitely an A+, and not just because I grade high


Jenn/ A, all the way

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