Michael, 39, is smart, handsome and oozes confidence-and that's the problem.
Michael is looking at me as if I’ve never been in a gay bar before. It’s Saturday night, 10pm; we’re at Cocktail, and I’ve just told him about the stools I had reserved by the window.
“Actually,” he says, “I think standing in the middle of the room will give us greater…access.” Michael should know: He’s spent a lot of Saturday nights in Boystown. And on those nights, he’s met plenty of boys. But he hasn’t done it by sitting on the sidelines. In fact, Michael doesn’t sit at all. He stands, he scans the crowd, he takes a walk around the room to see who’s there. And when he sees somebody he likes, he has no qualms about approaching him.
He notices a guy in chunky black glasses. “Cute,” he says. Soon, a half-naked go-go boy saunters up to the guy, who promptly puts his hand on the go-go boy’s ass. “Ew,” Michael says. “Turnoff.”
Subtly buff, with silver Anderson Cooper hair and shimmery blue eyes, Michael could have almost anybody in the place. But his problem isn’t meeting boys—it’s keeping them. After chatting at the bar, plenty of guys agree to go on a date with Michael. But pretty soon they say they only want to be friends. “I come on too strong,” he theorizes.
Lately, he’s making an effort to tone it down. For example, the night before, Michael went on a date with a guy we’ll call Charles. Michael knew he liked Charles, but instead of calling or texting, he kept his excitement in check. “I’m waiting for Charles to contact me,” he says proudly.
Maybe it’s because he has Charles on the brain, but after two hours at Cocktail, he isn’t seeing anybody who interests him. We decide to go next door to Sidetrack for one more drink. There, we once again stand in the middle of the room, where boys are forced to rub against us as they squeeze by. Michael says hi to a few of them. “Slept with him,” he whispers to me as some of them pass.
Finally, he sees a guy in a T-shirt that suggests he’s all muscle underneath. “That guy’s my type,” Michael says. “But he’s not going to talk to me.” Minutes later, Muscles is in front of us.
“Don’t I know you?” he asks Michael. I roll my eyes and look away, but Michael takes the bait. When Muscles goes to the bathroom a few minutes later, Michael says, “He’s probably not going to come back. I don’t think he’s into me.”
Ten minutes later, Muscles is back. Thirty minutes later, Muscles is giving him his phone number. Forty minutes later, Michael and I are in a cab, where he’s telling me how, as part of his new dating strategy, he’s going to wait for Muscles to contact him. Which he doesn’t think will happen.
The next day, though, Muscles texts to see what’s up. But Charles sends an e-mail saying he only wants to be friends.
Steinmetz thinks Michael has another problem besides being overly eager. “You’re too good to be true,” she says. It’s true: Michael’s good-looking, successful and interesting. Most of all, confidence wafts off him like cologne. To most guys, Steinmetz says, that can be intimidating. “Look at the power dynamics,” she says. “Who’s more attractive? Who’s taller? Who’s more assertive?” Because Michael is looking for guys who are more laid-back (read: shier) than him, he’s usually going to be the one with the power. Steinmetz suggests giving some of that power to the other person by asking questions that require more than a “yes” or “no” answer, and waiting for them to answer it at length. (And if they’re short, maybe crouch down to their level.)
LET’S TRY THIS AGAIN
Suspecting that Michael’s regular haunts (Sidetrack, Manhunt.com) probably won’t yield relationship results, I take him to Guerilla Gay Bar, a monthly event where gay men converge on an unsuspecting straight bar in the South Loop. This night, 100 of us descend on Bar Louie.
Realizing we’re in for a long wait at the bar, we stand behind a tall guy Michael thinks is cute. Soon Tall Guy is talking to him and offering to buy our drinks. But Tall Guy is too similar to Michael—he’s very confident and leads the conversation. Michael’s bubbly personality is smothered.
“Let’s take a walk,” I suggest. As we stroll around the bar, we notice Muscles. “Let’s see if he comes up to me,” Michael whispers. He doesn’t. And Michael doesn’t approach him either—not even when the two come face-to-face as we leave Bar Louie and try to flag down a cab. His new dating strategy may need some rethinking.
Want to date Michael? E-mail email@example.com.
FAMILY & FRIENDS
“After one evening of great conversation, a cocktail or two and a kiss good night, Michael begins planning the next ten years of his life with that person.” —Kathy, friend
“If you give it up too soon, that’s going to be the extent of the relationship. How often does ‘hooking up’ lead to a long-term relationship?” —Kathy, friend
“When meeting new people, he seems to be the one initiating most of the communication without letting the other one meet him in the middle.” —Sam, friend
“I’ve advised him to let his interest be known and put it in the other person’s court to see if they act. Let it be mutual to see if you’re on the same page.” —Sam, friend
SHIFTING POWER DYNAMICS
We’re told to have confidence when dating. But that confidence is so rare that we actually don’t know how to react to it when we see it. The key, Steinmetz says, is to be quietly confident.
When talking to somebody at a bar, think about who has the upper hand. It’s a bit awkward, but think about who is more attractive, who’s more successful, etc. If that person is you, shift some power to the other person through the conversation. Let the other person talk, and do your damnedest not to interrupt him or her.
Don’t be too quick to express interest. Yes, it’s honest. But it also can come off as aggressive.