I am what adults euphemistically call a “late bloomer.” As a boy, I had more Dungeons & Dragons characters than friends—and more fear of girls than of dreaded gym class. This did not go unnoticed by my peers. In my seventh-grade yearbook, a “friend” scrawled the following valediction in black Magic Marker across an entire page: 2-4-6-8, you will never get a date!!!

High school came and went with no new developments. Four years of college followed. Nothing.

I had hoped I’d outgrow my discomfort with the fairer sex, but my relationships with women remained infrequent, unsatisfying and brief. Ten years passed and my yearbook prophecy took on monolithic proportions. Just what the hell was wrong with me, anyway?

Then, during a particularly acute late-night spasm of drunken self-pity last year, I began to research the cause of my misery online. I discovered plenty of “expert advice” on how to pick up women; a lot of it was contradictory, and some involved acting like an asshole. Nonetheless, I devoured it. But when I tried to use it, it fell flat or, more often, I lost my nerve. I needed something much stronger: personal instruction.

My research led me to a social-coaching company called Charisma Arts (charismaarts.com). For a sizable fee ($1,399), their self-styled Casanovas would spend a weekend teaching me how to approach women, and then how to talk to them once I was there. Several field trips to local nightclubs—including a few outdoor bars—would put me through my paces. It seemed like a bargain.

An educational DVD arrived in the mail, and I spent the weeks leading up to my boot camp absorbing its lessons. Their approach was based on becoming more “emotionally sensitive.” That was alarming—being sensitive was what got me into this mess in the first place. On the other hand, they promised I’d get results without memorizing disingenuous pickup routines or pretending to be somebody else. I liked the idea.

Class began on a gray Friday afternoon in a midtown dance studio. We tried some conversational exercises. I practiced eye contact by staring into a fellow student’s eyes for a minute straight. During a role-playing exercise, I did a mock approach on an instructor. She was from Germany. Stuttering, I told her about how in Munich I was served a beer as big as my head. I felt lame.

The real test came that evening, when I reported to a chic rooftop nightclub in the Meatpacking District. Dimitri, a sharp-minded Russian instructor with an intense personality, put me to work right away. Placing his hand on my shoulder, he indicated a seated pair of Asian hotties across the room and looked me in the eye.

“I would like you to talk to them.”

“Uh…” I couldn’t think past my own panic, but neither could I back down. Light-headed, I wobbled over and introduced myself. “H-hi. How is your night going?”

They didn’t even look up. I sat down next to them, and said it a little louder this time: “Hi! Uh, how is your night going?”

This did not go well. One girl would only look at me sideways and gave one-word responses. Her friend ignored me completely. Soon, I bailed.

While my guide seemed to be charming every woman there, my trouble was far from over. It climaxed when a cute brunet actually ran away from me when I made a poorly planned approach from across the room, stepping over chairs and tables to get to her. Before I could say a word she darted into a corner and shook her head, crying “No!,” while her friends watched in amusement.

Then I did something that surprised me: I laughed out loud. And I went to talk to someone else. All my life I’d been petrified by the thought of female rejection. Now, not only was I confronting it, but I was taking the worst and moving on.

We went to another rooftop bar the next night, and my newfound resilience made me bolder and more successful. I spent the first half of the evening flirting with a comely 23-year-old from Long Island. The rest, I lounged with a gorgeous African-American girl, my hand resting on the small of her back.

Seven months after the boot camp, I’m still learning. My newfound social skills have made me more confident with everyone, not just women. Yes, I still fuck up—often—but that’s what the learning process is all about. And I feel I have the freedom to choose someone who makes me happy, not just settle for the first woman who comes along. Anyone out there into Dungeons & Dragons?