How to Be More Approachable to Women

Since #MeToo a lot of men have asked me how they’re supposed to flirt with women when every first move might be interpreted as harassment. I tell them to sit tight. Men should be nervous about approaching women, but that doesn’t mean you can’t take steps to make them feel more comfortable approaching you by looking as normal and inoffensive as possible.

Like my friend Rob (not his real name).

As soon as we walk into a bar—or a Sweetgreen, or an elevator, or a CVS—the attention of the women in the room shifts, subtly, to Rob. Eyes leave conversations to dart his way. Hair is tossed. Bodies twist ever so slightly toward him in their chairs, like sunflowers. It’s like the moment in World War Z before all the zombies start climbing one another to get over the wall to where the humans are hiding. I usually lose him in a CGI anthill of women after about half an hour. But he hardly has to do anything at all.

Rob is attractive—in a down-the-middle way, like the grown-up version of the most popular guy in high school if he hadn’t let himself go in college—but more than that, he’s extremely approachable. He manages to convey that he’s single, straight, and friendly through what he wears, how he acts, and even how he stands. I studied Rob for months until I had cataloged his charms. Then I called a summit of women to help me assemble a guide to approachability. These are our findings.

STEP 1: Dress Down—But Not Casual

When I suggested to Rob that he dresses “for women,” he agreed, with one qualification: “I dress to be comfortable,” he told me. I’d argue that dressing for comfort and dressing for women are the same thing. So would my friends.

I studied Rob for months until I had cataloged his charms. Then I called a summit of women.

“I’d also probably feel more confident walking up to a guy who’s dressed more casually. Fancy businessmen can be intimidating,” said Kaila, 29. “I’ve also used an interesting piece of clothing as a means of hitting on guys. It’s an easy conversation starter.” Break out those novelty tees, gentlemen.

Shannon, 29, suggested that men’s clothes should be “comfortable but also fresh” and pointed to comedian Hasan Minhaj as a reference. I’d never investigated Minhaj’s sartorial choices, but a quick Google search revealed some spooky similarities to Rob’s (cue X-Files theme). Both men dress down, but upscale down: They often wear white sneakers, but the sneaks are very clean; they generally wear jeans, with a T-shirt or sweater, but everything fits well and is in good condition—no wrinkles, stains, or holes. Their clothes are unintimidating, but not frumpy.

STEP 2: Bring a Buddy . . .

Having a friend or two around also makes you look less like a murderer. (Although, Shannon pointed out, a man who is “comfortably alone,” reading or somehow occupying himself, is very approachable.)

“If a guy is around a bunch of guys, it’s a good sign that he has friends and isn’t just prowling around a bar like a weirdo,” said Sophia, 26, adding that she’ll usually wait for a guy to separate from the herd—by taking a solo trip to the bar, for example—before she approaches. “I’m not going to talk to four guys when I just want to talk to one.”

The smaller your group, the more approachable you’ll be. “If it’s just him and a buddy, I’d probably be more likely to chat him up than if he’s in a large group of guys,” Eliza, 32, agreed, “especially if there are women in the group.”

STEP 3: . . . But Not a Lady Buddy

Rolling with female friends definitely makes other men jealous, but it also makes women less likely to approach you: We have no way of knowing whether that beautiful woman to your left is your friend or your girlfriend, and we’re not going to risk her wrath by shooting our shot.

STEP 4: Make Yourself Physically Available

As a little woman, if I’m going to approach a man, I have to see a clear path to him. My worst fear is that I’ll try to break into a phalanx of men to talk to one and none of them will hear me, so I’ll have to say “hey” progressively louder until I shout “hey” so loudly that the whole bar goes quiet and looks at me.

Nobody wants to talk to the brooding bad boy in a bar.

“I don’t want to have to come up from behind and awkwardly tap someone on the shoulder,” Kaila said. It can feel like “Hello, it’s me. Short lady. Down here. I swear I’m an adult.” Leave some space between you and your friends, and only sit down if there’s an open seat next to yours.

STEP 5: Don’t Be Sad

Women like the brooding bad boy onscreen (call me, Marlon Brando circa 1951), but nobody wants to talk to the brooding bad boy in a bar. Almost every woman polled in my grand summit of babes said she would not approach a man unless he was smiling a lot and having a good time—unless, in other words, he looked friendly and easily charmed.

Observe Rob: He begins to disseminate friendliness as soon as he walks into a bar. He jokes with the bouncer, he smiles at the bartender, and then he just sort of cases the room, beaming, for a minute. It puts everyone at ease. “I’m not approaching a guy who isn’t smiling. It just feels too dangerous to talk to a man who is serious, quiet, and trying to be cool,” Sophia said. “I’m not trying to get murdered.”

STEP 6: Remain Alert . . .

Use your friends to look less broody, but don’t get totally caught up in their chat. “One thing that has kept me from approaching a man is the feeling that I will be interrupting a conversation, or his enjoyment of whatever game he’s watching on the bar TV,” said Ashley, 29. “When I’ve approached men, it’s usually when they’re participating in a conversation but not engrossed in it, or when they’re watching something but also frequently checking in with what’s happening elsewhere in the room.”

“It just feels too dangerous to talk to a man who is serious, quiet, and trying to be cool.”

Women are very skilled at half participating: I’ve had many long, wonderful conversations with my female friends in which we all half-assedly throw in contributions every couple seconds while scoping the room. We may have arrived at a solution to world hunger during one of these discussions. We’ll never know. Nobody was paying attention.

STEP 7: . . . But Chill

While you’re having your half-assed but very enjoyable (smile!) conversation with your small group of wingfriends, be sure not to get too loud. In middle school, being loud and boisterous was a great way to signal confidence and get girls’ attention. In adulthood, being loud and boisterous suggests immaturity. It also suggests that you’re drunk. One of the cruel contradictions of flirting is that alcohol, which makes you feel comfortable approaching someone, also makes women less likely to approach you. So order a soda with bitters and sit tight. If you create the right impression (that you’re a nonmurderer with fun friends and clean clothes), the women will come.

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