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    Dinner with Cupid

    I said to myself, ‘Please let this be my date’

    She made a good first impression. Will he have the same effect on her?

    Tino Capobianco and Alison O’Connor.

    TINO CAPOBIANCO: 28 / community relations

    First thing people notice in his home: His signed memorabilia collection

    What makes him a catch: Passionate about public service and helping people


    ALISON O’CONNOR: 27 / educational coordinator

    Her interests: Volunteering as a hospital baby rocker, working with young children

    What makes her a catch: She is funny and kind.



    Tino I went for a run after work to clear my head.


    Alison I worked all day, came home and got refreshed, and then caught an Uber.

    Tino When I walked into the restaurant, I saw a girl standing at the hostess table. I said to myself, “Please let this be my date.”

    Alison I heard the door open behind me and saw a guy my age alone with a beautiful bouquet of flowers.

    Tino First thing I noticed was her smile.

    Alison He was very tall.



    Tino We broke the ice by discussing why we both decided to go on Dinner With Cupid. We shared some of our worst first-date experiences and decided that it was time to try something new.

    Alison He was very comfortable and dove right into conversation. We talked about our jobs and why we signed up for this dating experience.

    Tino She is a former teacher and now works at a local university. I was impressed with how successful and accomplished she is for a woman her age.

    Alison He is very proud of his hometown and dedicated to his community. It was nice to see the pride he has with all he does. He really loves his job and his family, and it was nice to hear.

    Tino We started off with the burrata and both ordered the seafood risotto. The service was excellent.

    Alison We thoroughly enjoyed it — absolutely delicious. The service was also amazing, and I would return.

    Tino I knew I was enjoying myself and was planning on asking her out for a second date. She had a great sense of humor and she was full of energy. I liked her from the moment I saw her waiting. I definitely felt a spark.

    Alison He was a very friendly and easygoing guy. The conversation flowed easily. We are both only children, are close to our families, and love our jobs.

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    Tino We spent over two hours together.

    Alison We finished the wine and our conversation. He offered to walk around the North End, but it was raining. I was ready to call it a night. He was super kind, but no chemistry. He offered to walk me to the train, but I called an Uber.

    Tino I walked her to her Uber and made plans for a second date. Goodnight hug with a kiss on the cheek. She texted me when she made it home safely.

    Alison There was a brief hug.


    Tino Yes.

    Alison No. He is a nice person, but I didn’t feel a connection.


    Tino / A+

    Alison / B  

    GO ON A BLIND DATE. We’ll pick up the tab. Fill out an application at Follow us on Twitter @dinnerwithcupid.