Laughing all the way

His perfect Saturday: Making breakfast, doing something outdoors, dinner and drinks

Notable qualities: He’s adventurous, honest, active, and loves to travel.

Judy Fleming, 40, Special education teacher

Stranded on an island, she’d want: Chocolate, her two kids, The Office

In a date, she’s looking for: An easygoing demeanor, sense of humor, and love of sports

7:15 p.m. Chiara Bistro, Westwood

Early Advantage

Jeff: I was looking forward to the date and more curious than nervous. What’s the worst that could happen? Gulp!

Judy: I got to the restaurant early. In the waiting area I met two lovely women and when I told them why I was there, we launched into conversation and immediate friendship. We happily scrutinized all the men who came in.

Jeff: I noticed Judy right away, as she was the only person that wasn’t with someone else.

Judy: Laughing with relief, I hugged him. I may have shocked him, but he was a good-looking man with a particularly nice smile, and I was thankful.

Applause, Applause

Jeff: I thought Judy was attractive. She seemed a bit nervous at first, but the conversation flowed pretty well, so that helped. I’m a pretty laid-back guy, so I think that helped, too.

Judy: Very soon we were comfortable and chatting away.

Jeff: We were talking so much that the waitress finally said to flag her down when we were ready to order.

Judy: We covered politics, religion, health, nutrition, music, movies, books.

Jeff: Judy is deep and likes to meditate, so I enjoyed learning more about that. She also worked for a sports radio station, and I am a big sports fan.

Judy: We have almost nothing in common but a good sense of humor; we were able to laugh about the differences.

Jeff: We talked about a variety of topics and mostly discussed current events. She’s smart, and I like that.

Judy: I think we both had our concerns -- he has never been married, which made me wonder aloud about his desire to commit, and I think he worried a bit that I have a pet pig that sleeps in my bed! Differences aside, we shared many smiles and toasted to a wonderful evening.

Jeff: Although we have some different interests, I felt more comfortable as the date went on.

Judy: The food and service was superb. The waitress brought us to the kitchen, where there was more light, for a picture. The staff clapped for us!

Further Adventures of J & J

Jeff: I recommended a nightcap at a new place nearby, and I was glad she was up for it. Extra points for spontaneity!

Judy: We went to a bar, where we enjoyed the end of a Celtics game (I guess we do have something in common) and shared one more drink. He walked me to my car, we hugged, and he snagged a kiss on the cheek.

Post-Mortem

Judy says: He was definitely an A!

Jeff says: A-

A Second Date?

“I’d like to see Judy again,” says Jeff. “She was easy to talk to, cute, and someone I’d like to get to know better.”

GO ON A BLIND DATE. WE’LL PICK UP THE TAB. To apply for Dinner With Cupid, fill out an application at boston.com/cupid.