The Gay-Dating Coach

Jim Sullivan is a gay-dating coach. But there’s something of the religious fanatic in him, too. After all, he was a Christian Brother (and also a teacher, guidance counselor, and principal) before he found his true calling ministering to Manhattan’s gay, single, and suffering.

Right now he’s coaching me at Big Cup, the cruisey coffeehouse in Chelsea that can put even the most confident gay single guy on edge. “A lot of successful professional men tell me that this setting is impenetrable,” Jim is saying with missionary fervor. “But you must tell yourself you have a right to be here.”

We are sitting in two comfy chairs in the middle of the room while impossibly cute men swoop past with lattes and iced mochas. “You like that one on the couch there?” asks Jim, youthful at 55. “He’s like a young James Dean.” When he isn’t conducting singles workshops, Jim brings guys here to practice getting dates, and he thinks of what we’re doing as hunting. But for me, it’s more like bird-watching. I am most intrigued by a redheaded-woodpecker guy on the couch. But the raven-haired writer at the table by the men’s room is cute, too. “I can’t just go up to him and say hello,” I quack. Jim has heard this hundreds of times before. I focus on the writer by the restrooms. “When you try to get him to notice you, use a soft focus with the eyes,” Jim tells me with big-brotherly concern, “not the hard stare you’d use in a bar.”

I do as he instructs, and my prey glances back. We have liftoff, I think, so now Jim hands me his list of icebreakers. It includes “I’d like to take those eyes home with me,” “I love your Fire Island T-shirt,” and “Weren’t you in the marathon last year?” I reject them and come up with my own, and Jim approves it. Quite simply, though, I can’t stand up. “Just relax and keep on breathing,” he coaches. “Don’t tell yourself you’re not good enough, don’t despair, or you’ll never act.” I can’t help it. I’m absolutely paralyzed with fear.

What’s up with gay men anyway? Why, in this open, accepting society, are we so screwed up about dating that Brad Gooch had to publish a book last year called Finding the Boyfriend Within? Jim, whose business is called Dating Strategies, has his theories, and none of them make reference to Sex and the City because he finds men-with-men a completely different situation from men-with-women. “Ninety percent of all gay men are too competitive to humble themselves and say hello,” he says. “Women are more cooperative and accepting. That’s why you see attractive women with guys with bellies. Gay men have more anxieties because they had no support while dating as teenagers. Now, even with great bodies and careers, they are so inept at dating that it can put them in tears. But I believe meeting potential boyfriends is a technology that men can learn. Most men come to the Big Cup to meet somebody, but they have no idea how to do it.”

Meanwhile, the potential love of my life is still sitting in the back, furiously writing in his notebook. Once more, Jim suggests I go over and try an icebreaker. I force myself up, and then, dammit, sail right past him into the bathroom, lock the door, and bang my fist against the sink. In the mirror I see that my pupils are dilated, as if I were on acid.

With a deep breath, I yank open the door, storm out of the bathroom, linger for a second, then hit him with my well-crafted icebreaker. “Writing the Great American Novel?” I ask. Bang! He slams his notebook closed, mumbles, and then resumes writing as if I weren’t there. Disaster. I scamper back to my perch. But when I tell Jim what happened, his face lights up. “Congratulations!” he says. “You just did the hardest thing by approaching someone, introducing yourself, and getting a response.”

Next time, he suggests, I might want to say “Excuse me” first because it’s less startling to a stranger. But he’s proud of me and wants to know how I’m feeling. Like a booby and a failed hawk, I’m afraid, but also giddy as a dog chasing squirrels. “I should have talked to him,” I sigh. Jim, who teaches everything from “spiritual dating” to “romantic obsession” in his formal seminars, leans in. “Don’t ‘should’ on yourself,” he says. A minute later a brown-haired cutie-bird is alighting near us with a copy of Time. Jim gives me a conspiratorial nod. “That magazine,” he mutters, “is a prop.”

The Gay-Dating Coach