ANNA WEBSTER > 23
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WHY SHE’S A CATCH > I like going out on adventures, camping, but also like to class it up and go out for drinks.
WHEN SHE’S HAPPIEST > When I can dig my toes in the sand.
MIKE IANNOTTI > 27
ON A DESERT ISLAND, HE’D WANT > My iPod, a boogie board, and a lighter.
WHEN HE’S HAPPIEST > Driving into the sun on an empty road with the windows down, blasting Dave Matthews.
7:30 P.M. L’OSTERIA > NORTH END
>STEADY AS WE GO
ANNA [Before the date], I read some previous Dinner With Cupids, which made me more nervous.
MIKE I was excited, but I ended up having a really busy day at work, so I didn’t have much time to think about it. I left the office a little late, so I thought I was going to be behind schedule.
ANNA Mike was a few minutes late, which gave me just enough time to text my friend the play-by-play.
>LOOKING AT YOU
ANNA I walked in and saw a guy sitting alone at one of the tables, so I walked up and introduced myself. Then he told me I had the wrong person and he worked for the restaurant.
MIKE I saw a girl sitting by herself along the back wall and figured it was probably Anna. I was just about to walk over, but the hostess showed up and asked if I was Mike. Was it that obvious? She stood up from the table to meet me, which I thought was classy.
ANNA To my relief, he seemed calm and outgoing.
MIKE She was cute and looked good in black.
>GOOD GOOD TIME
ANNA We have a lot in common – we both are older siblings with family who attended BU, we both are pretty intense Dave Matthews Band fans, and we even ordered the same dish.
MIKE Turns out she went to the same school and has part of the same major as my sister. I thought Cupid was supposed to match someone up with me!
ANNA [Both of] our moms had convinced us to sign up for the date.
MIKE We’re both big Dave Matthews fans, so we talked about shows we went to and favorite songs.
ANNA I felt comfortable because I could tell he was being himself. The conversation was easy; Mike has a good sense of humor.
>THE LAST STOP
MIKE It was 9-ish, we had finished dessert, and the restaurant was emptying out. I suggested we check out the bars by Faneuil Hall and pick one for a drink.
ANNA I was up for it, which is a good sign, because I usually don’t stay out late on weeknights.
MIKE We were both taking the Green Line back, so we rode together.
ANNA As we approached Mike’s stop, we realized we hadn’t exchanged numbers. He stayed on to grab my number and then got off at the next stop.
MIKE We only had time for a quick hug. My stop came up sooner than I thought.
MIKE I’ve never been on a blind date before, so it’s hard to say. B+? A-?
ANNA Sure, we have enough in common and seemed to click well.
MIKE I think so. If there were a Dave Matthews Band concert coming up, I think it’d be a pretty safe bet.
– Compiled by Marian DaniellsGO ON A BLIND DATE. We’ll pick up the tab. To apply for Dinner With Cupid, fill out an application at boston.com/cupid.