25 / EDUCATOR
WHAT DROVE HIS EXES NUTS?
I can be a little indecisive.
WHAT HE WOULD NEED ON A DESERTED ISLAND
Music, books, alcohol
24 / RISK ADVISER
WHO WOULD PLAY HER IN A MOVIE?
WHEN SHE IS HAPPIEST
When I finish up a great workout and I get to spend my day with friends
8 P.M. TOSCANO, HARVARD SQUARE
DREW Definitely downed a brewski before the date. I am walking into a blind date. . . . I was at least going to have a buzz while this all went down.
STEFANIE I had a glass of wine while I got ready.
DREW My state of mind before the date was pretty cynical. I basically was preparing myself not to be disappointed and setting my expectations low.
STEFANIE I was optimistic — I knew I was going to have a good meal and hopefully meet a good guy, too.
> THE KICKOFF
DREW The host brought her to the table. I was sort of relieved. I thought she was quite cute. Dressed nicely, seemed like a classy girl.
STEFANIE I could tell even when he was sitting down that he was taller than me. He was well dressed and had darker hair, which I like.
DREW She seemed pretty calm. I didn’t see her hands shaking or anything. She was willing to talk right away. No awkwardness at all.
STEFANIE We shared an awkward half-hug and laughed about it right away. He seemed like he was confident in himself. He was very upbeat, asked a lot of questions right off the bat, and seemed very engaged in the conversation.
DREW I discovered she has a great sense of humor and can be sarcastic like myself. I also discovered she is a big football fan. Talked and argued about sports. I tried giving her advice on her Fantasy Football league.
STEFANIE He told me he was a huge Ohio State fan. I went to University of Michigan for my freshman year of college, so we had a little rivalry there to joke about.
DREW I am glad she wasn’t mortified at some of my jokes and comments. I can be sarcastic and dry a lot and borderline inappropriate. She seemed to be able to take those in stride.
STEFANIE The conversation was really easy the entire night. We had a lot of the same general interests, so it was easy to talk to him.
DREW She is a big Eagles fan and I’m a Browns fan. We joked and commiserated about how bad our teams suck this year.
STEFANIE After we ate, we got one more drink at the restaurant. It was a mutual decision. I was having a good time.
DREW The date ended with us leaving the restaurant and me walking back with her.
STEFANIE He asked me for my number. After I gave it to him, he flagged me down a cab. We hugged and said bye.
> SECOND DATE?
DREW I would definitely be up for it.
STEFANIE I’d go out with him again.
— Compiled by Vanessa Fernandes
GO ON A BLIND DATE. WE’LL PICK UP THE TAB. Fill out an application at boston.com/cupid.