IT's DECEMBER WHEN I HEAR from a high-powered business wiz who says he loves climbing and skiing and describes himself as "fairly successful, well-traveled, and cultured."

He's obviously pretty confident, but I'm more than willing to find out if it's warranted.

On a sunny Saturday, Mr. Wiz and I meet for a walk in Greenwich Village. He's a good-looking, angular man with blond hair, and though he's not my usual type, his interests make him seem pretty hot. We spend a few weeks figuring out what to do on a date. Then he e-mails and asks if I'd like to meet him at an indoor climbing gym.

"Absolutely," I tell him.

I also admit that the last time I went climbing was the only time. I was 11, at sleep-away camp in Vermont. At the critical moment—when I was supposed to lean back and rappel off a 20-foot cliff—I suffered a major panic attack. I stood there for an hour before I made it down.

"So you have trust issues?" Mr. Wiz asks.

"I'm sure you'll be fine under my mediocre tutelage," he goes on. "But start doing those pull-ups!"

We meet a few days later at a Manhattan climbing gym, a no-frills joint with a hipster vibe. The place booms with the sounds of industrial rock and the occasional Santana tune. Twenty-something yoga girls and climber geeks are splayed every which way on molded-plastic "rocks."

Mr. Wiz, who will soon be my belayer, gathers up our gear and hands me a harness. Once I've cinched the contraption around my waist, he grabs the front of it and yanks tight, causing my hips to thrust toward him. I suddenly feel like I'm in an S&M film.

"OK, climb!" he says, pointing to a 15-foot wall. I grab on to a rock and start moving, making it halfway up pretty easily. I smile down at him. There's definitely a kind of tension between us, but I'm not sure it's the right kind.

"Don't let me fall," I say.

"I won't let you fall—I don't want to lose my membership," he replies.

"So this is about you," I say, stepping onto a tiny green foothold and hoisting myself to the top of the wall. Maybe I'm just in a kvetchy mood, but I feel like needling him.

"Life is about self-interest," he gibes back.

When I'm back down and untied, he takes me to a place where you practice upside-down climbing. There are floor mats and, close above them, a rock-studded pitched ceiling. If I decide to jump his bones, this is the place to go for it.

"It took me six months to master this," he says, scampering effortlessly up the incline. I look at him dripping with sweat. He's a pretty sweet-looking package, to tell the truth, but somehow I know the chemistry is missing. It's clear he feels the same way, and it's obvious to both of us that there won't be a meeting number three.