63 / ACCOUNTANT
STRANDED ON A DESERT ISLAND, HE COULDN’T LIVE WITHOUT
A female companion, a grill, and a book on astronomy
WHO WOULD PLAY HIM IN A MOVIE?
52 / ENGLISH TEACHER
WHY SHE’S A CATCH
I am a strong woman [and] also a romantic.
THE LAST THING SHE READ
8 P.M. VINOTECA DI MONICA, NORTH END
JIM I am a creature of habit, so doing this was a stretch.
ANNE I changed my outfit three times.
JIM I was a nervous wreck. I decided to walk to the [restaurant].
ANNE I got there early, so I walked around a little.
JIM I got there about 10 minutes early.
ANNE He was already sitting at a table.
JIM I just wanted to meet Anne and get the date started.
> THE PLAYERS
ANNE He looked nice.
JIM I was stunned at how beautiful she was.
ANNE He seemed a little nervous. I don’t think [we] knew where to start the conversation.
JIM We were through the awkward beginning in no time. We discussed our families and careers and what brought us on the date.
ANNE He talked for several minutes before he realized he was monopolizing the conversation.
JIM Anne is a devoted mother and passionate about her work. She is also a follower of [the show] Survivor. I wish I had said I would never vote her off the island.
ANNE I had linguine in tomato basil sauce.
JIM I ordered pasta with calamari. We shared everything.
ANNE I can’t resist homemade pasta.
JIM Both were quite good and the service was even better.
ANNE We had a lot in common.
JIM We were English majors in college.
ANNE We both had been married for at least 20 years.
JIM We are committed to our children and concerned about our health.
ANNE I felt like [Jim] was a bit more interested in me than I was in him.
JIM I thought, Anne would be a catch.
ANNE James was really easy to talk to, but I never saw him as a romantic partner.
> TRIBAL COUNCIL
JIM I asked if she wanted to go out again.
ANNE He invited me for a walk and to have coffee and dessert, but I turned him down.
JIM Anne said she had to get home so she would be ready for work in the morning.
ANNE I took his number, thanked him, and left while he stayed to pay. . . . I think my guard may have been up from the start.
JIM We said goodbye in the restaurant, no hug, no kiss.
ANNE He was a perfect gentleman and will make some woman happy someday.
JIM I would, but it’s up to Anne.
ANNE I don’t see a future for us, but I wish him the best of luck in life and love.
— Compiled by Steph Hiltz
GO ON A BLIND DATE. WE’LL PICK UP THE TAB. Fill out an application at boston.com/cupid.