Approaching a Woman Who's With Her Friends: Do's and Don'ts

Sunday morning at the farmers market. She and a friend are standing at a stall, debating whether a $14 jar of hot honey is a reasonable life choice. The friend is firmly in the "absolutely not" camp. You're right next to them, holding the exact same jar.

When it comes to approaching a woman who's with her friends, a lot of guys assume the first job is getting her alone. We'd suggest the opposite. Her friends aren't obstacles between you and her. They're part of the conversation. Talk to everyone, make sure nobody's left standing there, and if a friend steps in and steers her away, that's the end, not a challenge to get around.

Those two rules matter more than any opener. Below are five common situations: how to read each one, what to do and what not to do. We're writing "she" because that's the version we get asked about most, but the same rules apply whoever you're approaching.

Situation 1: She's with one friend

How to read it: They're browsing, wandering, laughing. Not having a serious talk, not rushing anywhere. A shared moment like the hot honey debate is actually an easy opening, because you're all in on the same thing.

What to do: Open to both of them, not just her.

"I'm with you, fourteen dollars is a lot. I'm also clearly about to buy it."

If they both laugh, stay on that thread and widen it naturally: "Do you two come every week, or is this a special trip?" If you're interested in her specifically, it's fine to say so once things are going: "Honestly, I came over because you seemed fun and I wanted to meet you." You don't have to lower your voice or wait until her friend wanders off. An honest reason for being there doesn't need hiding from anyone.

Don't: turn your back on the friend and talk only to her, or ask, "Mind if I steal her for a minute?" The first leaves the friend stranded, and she'll be distracted checking on her. The second asks her to step away from the person backing her up, which makes saying no harder.

Situation 2: She's in a group

How to read it: Three or more people walking together are usually headed somewhere and not looking to be stopped by a stranger. Groups are much easier to meet where talking to new people is already normal: a friend's party, between rounds at trivia night, a climbing gym's social night.

What to do: Treat it as joining a group conversation, not extracting one person from it. Talk to the group, add to whatever they're discussing and let everyone in. If a one-on-one conversation with her happens, let it grow out of that on its own. For the step-by-step, see how to join a group conversation.

Don't: fall for the old advice to "win over the friends first." It's half right. Including her friends is right. Being nice to them as a strategy to lower her guard turns them into tools, and people can usually tell whether you're actually talking to them or working an angle.

Situation 3: Her friend doesn't seem comfortable

How to read it: Arms crossed, watching you, short answers, glancing at her as if to check she's okay.

What to do: Treat it as information, not resistance. Give everyone a little more space, keep it light and talk to the friend directly so it's clear you're not trying to pull anyone away. Then wrap up early: "I'll let you two get back to it. Good luck with the honey decision."

A friend might be wary for all kinds of reasons. You might be the third guy to come over today. They might have had a bad experience. She might just be the protective one in the friendship. Whatever the reason, the friend is looking out for her, and that's a good thing.

Don't: call her a cockblock, out loud or in your head, or try to convince her you're a good guy. You can't talk a stranger into trusting you, and the harder you explain, the more suspicious it looks.

Situation 4: Her friend pulls her away

This is the most important part of the article.

Her friend takes her arm and says, "Come on, we're going to miss the bus," or just, "We've gotta go." She looks back at you and smiles. A lot of guys read that as "she's into me, but her friend got in the way." That's not what's happening. A friend pulling her away might be helping her end the conversation, or they might really need to be somewhere. Either way, the conversation is over. The smile over her shoulder is almost always just politeness.

The only move:

"Totally, have a good one!"

Then let them go.

Don't:

• Say, "Wait, just give me one minute."
• Wait for the friend to head to the restroom or the car, then circle back.
• Drift along behind them to see if another chance comes up.
• Ask the friend to pass along your number, or to get hers for you.

What these have in common is looking for the moment when she's alone and it's hardest for her to say no. When her friend steps away, she isn't more available. She's less protected. Our lesson on her company as a boundary drills exactly this call. For the other ways people signal they're done, like stepping back, shorter answers or reaching for their phone, see she steps back, you step back.

Situation 5: You've got a friend with you, too

With two of you and two of them, the classic problem goes like this: you and she are getting along great, while your buddy and her friend stand there staring at the kettle corn stand. A few minutes later, her friend is bored and pulls her away.

Better: all four of you talk together, or you split naturally into two conversations where everybody's actually engaged. If you go quiet when your friend joins, or only talk to her, someone gets left out.

One thing to be clear about. Some dating advice calls it being a good wingman when your friend "handles" her friend so you can get her alone. That isn't teamwork. It's separating her from the person she came with. The goal is everyone feeling comfortable, not everyone being assigned a role. And if your friend gets pushy or keeps pressing for numbers, reining him in is your job.

What to say: the opener, the honest ask and the exit

Open to both of them, with something you're all looking at:

"Sorry to jump in. You two seem like regulars. Is the cider stand worth the line?"

If you'd like to get to know her, be honest and leave an easy out:

"This was fun. I'd like to keep talking to you. Want to swap Instagrams? Totally fine if not."

When it's time to go, say goodbye to both:

"I'll let you get back to your morning. Nice meeting you both."

Keeping everyone included is what our lesson on including her friends is about. For timing and how to say why you came over, how to approach a woman without making her uncomfortable has the full five steps. At a bar, her friends matter even more, and approaching someone at a bar covers the stop rules for drinking settings. More is on our approach topic page.

FAQ

Is it okay to talk to a girl when she's with her friends?

Yes, if the timing is right and you treat her friends as part of the conversation. Open to everyone, keep everyone in it and let them go when they want to go. Skip it if they're clearly in a private conversation, in a hurry, or one of them seems upset.

How do you approach two girls?

Talk to both of them. If, after a while, you'd specifically like to get to know one, say so honestly. Don't ask both for their numbers as a backup plan, and never flirt with one to make the other jealous. That turns people into props.

Her friend left, but she stayed. Can I keep talking?

If she chose to stay and she's keeping the conversation going, sure. Just keep it the same conversation. Don't treat it as your opening to get more personal or suggest going somewhere else. If she says she's heading out too, say goodbye.

What if her friend says, "She has a boyfriend"?

Take it exactly as if she'd said it herself. Thank them, say goodbye, leave. You don't need to figure out whether it's true. More in she says she has a boyfriend.