The Pickup Artist

Some guys have all the luck, and the ones who do are not always the best-looking, the smartest, or the funniest. They’re the ones who don’t give up. Tad Brock is one of those guys. A 40-year-old headhunter who looks like a slightly less attractive Anthony LaPaglia, he’s personable and animated, and his secret to wooing women is to act like one. He listens, loves to talk about feelings, and even does Pilates. By his own estimate, he’s slept with between 500 and 1,000 women. So why isn’t he happy?

Over drinks at the Tribeca Grand, he tells me his story. He doesn’t try to get laid, but often that’s when he gets lucky. “I don’t find that when you rush in to try to close a deal with any of these people, it really works out,” he tells me. “My immediate goal with someone is to find out what they’re about. I’ll meet a girl and I’ll decide she’s too hot for me, but I’ll go up and talk to her anyway because maybe she works at a client bank or maybe she’d be good for one of my friends. Sometimes pitching one of your friends to a girl is the best way to get her interested.”

“He’s not scared of anything,” says Rachel Nadel, a close friend of his. “He knows a little about a lot of stuff and can start a conversation about anything. I’ve watched it, or I wouldn’t believe it. He’s so confident that he becomes more attractive.”

More important, once he gets rejected, he doesn’t dwell: “He’ll just keep going. He’ll say, ‘She wasn’t into me,’ and he’ll move on. It’s a ‘There’s plenty of fish out there’ attitude.” Rachel says he’s such an operator that he’s surprised her sometimes. “I introduced him to a girlfriend this summer at a bar. I walked to the end of the bar to get a cigarette, and I come back and she’s making out with him. They had known each other twenty minutes, and she’s not a big public-display person. I said to her, ‘Eew! What are you doing?’ ”

“All these women on the Upper East Side, these gold-digging buck hos, they don’t care if you’re charming or sweet. It’s just, ‘Okay, what do you do for me?’”

It’s the “eew” part that interests me—guys might admire a guy who gets laid all the time, but few women do. A slut is a slut, regardless of gender. Laura, a producer in her mid-thirties, dated Tad several years ago and is now his good friend—and harshest critic. “If Tad’s the epitome of a successful New York City male, I might as well shoot myself right now,” she says. “He’s 40, he wants a family and kids, and he’s still single. How successful can that be?”

It’s a fair question. Tad has no girlfriend and not a prospect in sight—the most recent woman he dated dumped him because she felt he was too involved in the singles scene. Aside from picking up women in bars and clubs, he’s also used matchmakers,,, Eight-Minute Dating, It’s Just Lunch, and numerous blind dates, but still hasn’t met anyone he really likes. What does he think the problem is? Women, of course.

“The reason I’m not married is not because I can’t meet anyone,” Tad says. “I meet everyone. It’s not because I’m commitment-phobic. It’s because New York is really fucked up. All these women on the Upper East Side, these gold-digging buck hos, don’t care if you’re charming or sweet. It’s just ‘Okay, what do you do for me? Are you hot enough? Is your career good enough? Is your whatever big enough?’ If I thought this was what the world would be when I was 21, I would have gotten down on bended knee and married my college girlfriend.”

Laura thinks the problem lies within him. “One of Tad’s greatest strengths is his sensitivity,” she says, “but there’s a limit.” Laura and Tad met in a bar; she was getting over a breakup from an uncommunicative guy, Tad comforted her, and they began hanging out. “He healed a lot of things,” she recalls. “I got wooed into a friendship, and it almost became addictive. Here’s this guy who’s emotionally available at all times. It’s like Dial-a-Shrink. The turnoff is when he turns around and says, ‘Help me.’ He won’t put something to bed. I found myself saying, ‘I can’t talk anymore.’ I thought, Wait a minute. I’m the guy and he’s the girl. At the end of the day, I want my husband to be the guy.

“He has an issue with boundaries,” says Rachel, his friend. “Whenever he starts to date someone, he spends a ton of time with them and invites them everywhere. I need my own space and my own time to go out with my friends. When he’s in it, he wants in with both feet.”

Laura complains that he was so generous after they broke up that it got annoying—though, of course, she accepted each of his gifts. Sometimes they’d be talking on the phone and she’d complain about her tough day at work, and an hour later a grocery guy would show up with a delivery of all her favorite foods. “He’ll extend courtesies that are not asked for. Ultimately he is a do-gooder, but he takes it to such a degree because he so desperately wants to be in a relationship and be loved back that he’ll do anything.”

Over the next few days I try to figure Tad out. He’s a walking conundrum—a pickup artist with the heart of a woman, a sensitive guy who can turn on a dime, an anti-materialist who woos by sending groceries. Beneath all his warmth, he seems to have a bitter core, as though his years of playerly ways have made him lose respect for any woman who would have him. It’s obvious he wants love, but I know from firsthand experience that it’s hard to find love when you’re busy hitting on everyone in the room.

“Would I ever fix up my friends with him?” Rachel wonders. “Probably not, because he does go out and get laid, and he does discard easily. He would love to find the right person. But he will not settle down until he does.”

The Pickup Artist