Should You Approach a Woman Who's Already Talking to Another Guy?

Usually not while they're mid-conversation. Wait for a natural break, or until she's clearly drifting out of the conversation, then come over briefly and friendly. If you can't tell whether it's a date or a chat, assume it's a date and leave it alone.

Before you walk over, take a quick look at what you'd be walking into. In his approach guide at The Good Men Project, Dr. NerdLove lists the first question as whether she's there by herself or with friends. He also wanted to avoid being "interrupted by an annoyed friend (or date)." Approaching one woman alone is different from approaching a woman in a pair or a group.

A woman talking to a guy could be on a date, catching up with a friend, or stuck with someone who just walked up to her. From across the room you often can't tell which. That's the reason to wait instead of walking in. If she seems to be enjoying herself, leave it alone. If the talking has slowed and she keeps looking around, she may be ready for the conversation to end. Even then, you're not owed an opening.

Dr. NerdLove, writing in Kotaku, says to focus on women who are giving what he calls approach invitations: "signs that they're interested in you and would welcome your coming to talk to them." His bar example is a woman who locks eyes with you, looks away, then looks back with a smile. The other woman has noticed you looking and turned her back to talk to the bartender. The first one invited you. The second one said no without a word.

He adds that some women linger near you when they don't need to be there, or say something loud enough for you to overhear, hoping you'll respond. He also says to respect the setting: bars, parties, and networking events are places where people expect to be approached. A bus isn't.

A woman who's deep in a conversation with another guy has rarely sent you anything. If she hasn't looked at you, you have no invitation, so you're guessing.

1. Wait out of her eyeline. Stand nearby, doing something normal like ordering a drink. Don't hover or stare. Hovering makes everyone uncomfortable.
2. Watch for a break. He goes to the restroom, takes a call, or says goodbye. Or the two of them stop talking and look around.
3. Walk in from the front, not from behind. In that same guide he approached a seated woman from the front at a slight angle so she'd see him coming, which kept him from startling her.
4. Keep it short and low-pressure. Tell her up front that you only have a minute or two. In the same guide he says mentioning that you only have a few minutes gives her a built-in exit: if you overstay, she can say, "Didn't you say you had somewhere to be?"
5. Say one real thing. Something about the moment, not a line.
6. Read her answer. Warm and curious means keep talking. Short answers and a glance back at the other guy mean thank her and leave.

• "Hey, I saw you laughing over here and thought I'd come say hi."
• "Quick question. Are you actually enjoying this place, or are we all just pretending?"
• "You seem like you know what's good here. What should I try?"

If she's with him and he's still there, a small group-friendly opener works better than singling her out:

• "Mind if I jump in for a second?"
• "Sorry to interrupt, I just wanted to say hi. I'll let you two get back to it."

The second one costs you nothing. If she's into the idea of talking to you, she'll say so. If she's not, you've left on good terms.

Don't challenge the other guy. None of these will help you:

• "I was talking to her."
• "Bro, back off."
• "Let's see who she likes more."
• "She's with me."

Competing makes both of you look smaller. She's likely to stop thinking about who's more attractive and start thinking about how to get out of the moment.

Here are the three outcomes you're likely to see.

Both of you get tense. One guy says "Hey, what's up?" while clearly nervous. The other jumps in with "I was just about to talk to you," smiling too hard. She has to manage two men who both seem to care too much about getting her attention. She disengages, gives short answers, or talks to whoever seems calmer.

One guy backs off with a smile. He says, "Looks like you've got this," and walks away. The other guy keeps the conversation going without acting possessive. This is the cleanest outcome. The guy who stepped back looks socially aware, and the one who stayed has a much better shot because it's no longer a public contest.

One guy escalates. He talks louder, steps closer, or tries to out-talk the other guy. She can feel the tension, and she can tell neither of them is paying attention to her.

If you're the second guy to arrive, stay loose. Relaxed shoulders, no leaning in, no jaw-clenching, no smirking at the other guy. Then pick one of three moves: join naturally if the setting is a group, wait for a break, or move on.

You don't need to put him in his place. That's a movie fantasy. A calm, funny line works better:

• "Looks like I arrived during a very competitive moment."
• "Alright, I'll let you two continue the extremely important mission."

Then either keep talking casually or leave.

Take the hint and move on. You're saving yourself time. Dappered's "Ask a Woman" column describes the polite version of a no: "It was nice meeting you but tonight I'm hanging out with my girls." If you get that, say "Enjoy your night," and go. Some women simply dislike being approached at all, and the same column says to just move on to someone without that issue.

This is the easy case. Be social instead of territorial. "Mind if I jump in?" or "I'm joining this conversation, by the way" works, and if the energy is good you're part of the group instead of a rival in a silent duel.

• She turns back to him mid-sentence. Say "Nice meeting you both" and walk away. Don't linger.
• He gives you a cold look. Don't match it. Smile, nod, and leave.
• She says she's on a date. "Sorry, didn't realize. Have a good night." Done.
• You freeze. It's fine. Order your drink and try again with someone else. A missed approach costs you very little, and a pushy one costs you a lot more.

If she's talking to someone, you need a reason to believe she wants to be interrupted. If you can't name one, wait or move on. A calm man who knows when not to force it is a better bet than one who pushes in.