Blue crush?

Her perfect Saturday includes: Surfing on the Cape, then hanging out at a local bar

She’d like to date a guy who’s: Charming, with a good dash of funny thrown in

Bill Condon, 33, Financial planner

His perfect Saturday includes: Waking up on an island, scuba diving, and a sunset happy hour

His ideal mate would resemble: Sandra Bullock, Salma Hayek, Halle Berry combined

7 p.m. Gaslight, South End

LOOSENING UP Leah: I hung out with my girlfriends and put on my war paint.

Bill: I listened to the “Eye of the Tiger” on the way to the restaurant.

Leah: I was on time, and Bill was already there at the bar (showoff). I thought he had a nice smile and had put some effort into his outfit. I was happy about the lack of any man perfume or jewelry.

Bill: I thought she had a pretty face. I was trying to figure out her ethnicity, as she looked exotic. She has a nice smile and a friendly way about her.

Leah: Bill didn’t seem nervous, but that was probably because he was mostly finished with his martini.

GOING WITH THE FLOW Leah: We talked about my job and a certain article about what women experience in labor. I’ll let Bill give more details on this . . .

Bill: She is a nurse and delivers babies. We discussed whether it was possible for the delivering mother to have an orgasm during birth. I was reading a magazine article about this before I left for the restaurant. She seemed doubtful it could happen.

Leah: We’ve both traveled to Honduras and stayed at the same hotel. We’ve also both been to Costa Rica and have surf stories from the adventure.

Bill: She loves surfing, and I almost died surfing.

Leah: There was a revelation about him having a shark (or was it a dolphin?) tattoo that I’m on the fence about, but otherwise no major turnoffs.

Bill: We were pretty comfortable from the outset. We had a few giggles while discussing the childbirth article.

Leah: I got more comfortable as the date went on, because I was pretty sure Bill wasn’t a weirdo. Unless he’s got me snowed, I thought he seemed like a decent guy to have dinner with.

Bill: I think we both felt at ease throughout the night. Conversation flowed.

Leah: When Bill told me he has three sisters, I was like, “All right, he’s got to be well trained!” Definitely a plus.

GETTING COZY Bill: At the end of the date, she came to my side of the booth to take a picture. It seemed natural and a bit flirty. We had a nice table, so we just sat and chatted for a while. We both had an espresso and split a dessert.

Leah: By the time dinner was over, it was 10 o’clock. The date ended with us exchanging numbers and a good-night hug; ladies don’t kiss on the first date.

Bill: She was really nice, and I think we had fun. I wasn’t feeling a smooch, so I went for the hug.

POST-MORTEM Bill says: B+

Leah says: A-

SECOND DATE? She’s up for it. He says, “I don’t see why not.”

GO ON A BLIND DATE. WE’LL PICK UP THE TAB.

To apply for Dinner With Cupid, fill out an application at boston.com/magazine.