How to Approach Women & Start a Conversation Naturally
There are literally millions of tips on the internet on how to approach and have a conversation with women. But the funny thing is, you don’t really need 80 percent of it. Yes, you should have a general, high-level plan that guides the interaction. But you can also freestyle it, talk about the weather for 3 minutes, and have a woman fully engaged in that moment. You can also deliver every pickup move in the book with George Clooney charm and still get turned down.
I’m not going to tell you that none of the tips and tricks out there work. Some do. But there’s no way to guarantee a good outcome 100 percent of the time. And the tactics that are actually good only increase your odds. But success is never guaranteed.
Why do I point this out? Because with all these darn tips and tricks, some guys are literally trying to remember hundreds of things: tell a story, push-pull, get compliance, make it man to woman, and on and on. I’m going to give you some tips in this article too, because the title said I would, and I’m a man of my word. But men drive themselves crazy trying to remember so much, when there’s really one thing you need to remember. Grab a pen and a piece of paper, because this is going to be good.
Here it is: When you are in front of her, look relaxed, comfortable, and like you’re enjoying the moment.
Yep, that’s it. Act like this isn’t the first time you’ve ever talked to a woman, and your chances of having a chill conversation are decent, even if the subject matter is plain and a little boring.
In this post, we’re going to cover it all and prove to you that all this approach and conversation stuff we make out to be nuclear fusion is so much simpler than you think.
We’ll cover how to combat those crippling thoughts that make your feet feel nailed to the ground, how to start a good conversation and keep it going, and how to land the plane without getting weird, regardless of her response.
1. Before you walk over
I hate calling it an approach because the word approach feels like we’re about to do something nefarious. But I can’t think of anything better, so let’s stick with approach for now. Every approach comes down to 4 steps: what happens before you walk over, your opener, the conversation, and the close.
So let’s start at the very beginning. And we’ve all been there.
You see a woman you’d like to meet, and instead of walking over, you start listing reasons this isn’t the right moment. I call that the What-If Machine. What if she has a boyfriend? What if she doesn’t like my hair? Is my breath okay right now? I probably need some mints before I walk over. Yeah, the What-If Machine comes up with some scenarios that would make any movie screenwriter jealous.
But the What-If Machine can be beaten. And the way you beat it isn’t with brute force. It’s by simply being present.
Start by pausing that story you’re telling yourself and getting your butt back into the room or wherever you are, right now, in real time. Take one breath, feel your feet on the floor, and look at what’s actually happening in front of you. That’s what being present means, and it’s the part the dating gurus almost never talk about. Literally, just read the room.
Some things are real reasons not to go. She’s in the middle of a serious conversation with a friend, and it looks a little tense. She’s on the phone. She’s with a guy who could be her boyfriend. She literally looks pissed off for who knows what reason. Or you’re on a quiet street at night, where a stranger walking over would feel like a threat to her.
Could you walk up and interrupt anyway? Sure. Some guys do, and every now and then it works. Most of the time, common sense and a little courtesy say wait for a better moment, or let this one go. That’s not an excuse, by the way. That’s reading the moment and having some social intelligence.
But a lot of the time, the excuses we make, like she’s reading, browsing, waiting in line, or just generally busy, are exactly that: excuses. There’s some gray area here, I know. But that’s life, my friend. Not many things are black and white, especially when it comes to dating.
But as a general rule, take a step back and look at it holistically. If you know you should be approaching women and a week has gone by without talking to a single one, you either live at the North Pole, where there are no women, or you’re talking yourself out of good opportunities all week. That’s usually the What-If Machine doing its job well.
So, back to this moment. Ask yourself one question: could she comfortably talk to a stranger for 2 minutes right now? If the answer is yes, count to 3 and go. Reading the room takes one look, not 5 minutes. If you’re still reading it a minute later, you’re back to making excuses.
Sometimes she picks the moment for you. A glance that holds a second longer than it needs to, a quick smile, turning slightly toward you, playing with her hair as she looks your way: those are often her ways of saying she wouldn’t mind you coming over and saying hello.
Monica Moore, a psychologist, catalogued 52 of these signals by watching more than 200 women, then found that the women who used them most were the ones men approached most. But don’t make that a crutch. You don’t need a signal to walk over, but when you get one, that’s your cue to get those feet moving.
If you want to read a bit more about getting past the nerves, check out the Approach anxiety guide that gives you 6 ways to get moving.
2. Your opener
Okay, you made it. You walked over, and you’re standing in front of her. We tend to immediately make the focus, “What’s my opener?” But put that aside for just a second. Keep those memorized lines in your pocket for a beat. Why? Typically, she doesn’t care about your lines.
Here’s what she wants to know about you in those first moments: Is this guy dangerous? Is he projecting that he is comfortable in this moment? And does he make me feel comfortable?
The first question gets answered fast. Janine Willis and Alexander Todorov, psychologists at Princeton, found that people shown a photo of a face form a read on how trustworthy it looks within a tenth of a second. So part of the safety check happens before you’ve said anything, from how you walk up and where you stand.
The other two questions take longer. She needs to hear a few words out of your mouth and watch your body language before she decides whether you’re worth flirting with, weird, or a threat. That’s good news, because those are the parts you have some control over.
Calm and comfortable has a look, and it’s mostly things you stop doing. Stop fidgeting with your phone, your keys, or your drink. Talk a little slower than your nerves want you to. Look at her the way you’d look at a friend, which means holding her eyes and occasionally looking away, not staring. Stand still instead of shifting your weight around. None of it needs to be perfect. You just need to look like a guy who’s comfortable where he is.
Your opening line is the part every guy over-prepares, and it’s the part that matters least.
An opening line’s only job is to sound normal and give her something easy to respond to. In the 1980s, a psychologist named Chris Kleinke had more than a thousand people rate opening lines a man might use in a bar, a restaurant, a supermarket, a laundromat, or on a beach. The lines sorted themselves into 3 kinds. There were cute ones, which are basically canned comedy. There were plain ones, a simple comment about whatever was going on around you. And there were direct ones, where you say hello and admit you wanted to meet her. Women rated the plain and direct lines best and the cute ones worst, and they disliked the cute ones more than the men in the study did, which is worth knowing if you’ve been taking your material from other men.
Now, I know this is a little controversial, but there is nothing wrong with having 2 or 3 openers in your pocket so you aren’t inventing one under pressure. You don’t need 20 of them, and remember what the study said: you don’t need to be cute or funny.
Plain openers do the job: a comment on something around you, a direct hello with your name, or “How’s your day going?”, which works more often than you’d think. The easiest plain opener is saying the obvious thing. It isn’t witty, and on its own it’s neither good nor bad. Paired with a smile and relaxed body language, it’s a decent way to start a conversation, and it works just as well in the middle of one.
Another one that’s so simple but works: “I saw you standing over here and knew I needed to come over and introduce myself.” It’s direct, and it says the thing you’re both thinking. It breaks the tension in a good way and takes away some of that feeling of danger. In her head, he’s not dangerous. He just wants to say hello and probably flirt a little.
Being direct means she’ll know you’re interested, and that’s fine. One response worth having ready: if you go direct, a lot of women will ask why, usually something like, “Why’s that?” That isn’t her shutting it down. She’s checking whether there’s a person behind the hello, and the true answer covers it. You liked her jacket, you liked what she was reading, you liked her style, or you just thought she was attractive and wanted to see what else is there. Say the real thing and keep going.
Let’s say she’s got 2 muffins and a coffee, so you smile and say, “The muffins here must be good.” If she’s got one muffin, “Are the muffins here any good?” She’s in gym clothes, so you ask, “Do you go to one of the gyms around here?” She tells you which one, and you say, “I’ve been thinking about checking that one out. How do you like it?” At a party, “How do you know the birthday boy?” works at just about any party you’ll ever be at. It doesn’t need to be perfect or smooth. The point is, confident small talk beats the nervously delivered perfect line every time.
3. Keeping the conversation going
If you’re caught up in your nerves, or just not really present in the moment, the conversation usually doesn’t go well. When you’re stuck in your own head, you can’t do any of the things that make a conversation work. You can’t read her body language. You can’t listen to her answer before you respond to it. And when she hands you an opening, something she says that’s basically begging you to add on or ask a follow-up question, you’re going to miss it, because you’re too busy wondering how you’re coming across.
Nerves are your attention pointed at yourself: how you sound, what you’ll say next, whether it’s going badly. A team of psychologists led by Erica Boothby studied conversations between strangers and found that people consistently underestimate how much the other person liked talking to them, and the shyest people underestimate it the most. The reason came down to where their attention went. They spent the conversation replaying their own mistakes in real time, while the other person was judging them far more gently.
The way out is curiosity. Curiosity adds an extra obstacle for your anxiety and nerves to cross before they completely take over. It’s harder to worry about how you’re coming across while you’re also trying to figure out who somebody is. So ask yourself that question: who is this person? Ask it before you walk over, and then ask it again during the conversation. Notice something about her. Maybe it’s a bracelet you’ve never seen before, so you ask where it’s from. Now you have something to say, and your attention is on her instead of on you.
Todd Kashdan, a psychologist at George Mason University, has studied what curiosity does in conversations between strangers. The research assistants who talked with curious participants said they felt closer to them and more attracted to them, and that held even after accounting for how socially anxious the curious participants were. Curious people also enjoyed plain small talk more than everyone else did. Those were conversations with research assistants, not dates, but the finding points the same way as everything else in this post.
You need the boring questions: Every dating blog tells you not to ask interview questions, but you actually kind of need them.
Where she’s from, what she does, how she knows the host: questions like that are the backbone of small talk, and of flirting too. They’re how you find the thing worth talking about. You can’t ask an accountant why she went into accounting until she’s told you she’s an accountant. But questions are only a piece of a conversation. The other important part is what you do with her answers, and what you give her back.
It goes without saying that you shouldn’t ask 5 closed-ended questions in a row. That’s a rapid-fire interview. Ask the normal questions, and then, while you are being both curious and present, actually listen to her answers.
Every answer she gives you has a few threads hanging off it: a place, a person, something she’s excited or annoyed about. Pick one and pull on it, instead of moving on to the next question in your head. Save the ones you don’t pull. If the conversation stalls later, going back to one (“Wait, you said you’re from Atlanta. What do you miss most?”) shows her you were listening and gets things moving again.
The best threads to pull are the ones with a feeling attached. When something she says catches your interest, that’s when a why question works. If she tells you she’s an accountant, “I don’t get an accountant vibe from you. What made you go into it?” isn’t a personal question, and she doesn’t have to tell you her life story, but now she’s telling you something she actually thinks instead of reciting a job title. Same with a trip: skip “What cities did you go to?” and ask, “What’s the one thing from that trip that stuck with you?”
Then give her something back. Tell her what you think, relate it to something of yours, or tell a story if you’ve got a good one. Keep stories under 60 seconds, and hand the conversation back to her when you’re done. That’s how two strangers end up in a real conversation instead of a Q&A.
Some teasing can be helpful: Once it’s comfortable, you can let it get a little playful. A light tease is what moves things from friendly to flirty: push a little, then pull right back. She tells you she teaches kindergarten, so you grin and say, “So you’ve got zero patience for anyone misbehaving,” and then, “Honestly, that takes a special kind of person.” Keep it about something she chose, never something she might be insecure about.
These are suggestions, and they work just fine. But if you don’t want to throw in any of those elements and you’d rather stay on the small talk path, like I said earlier, that can work too.
She mentions she has a dog, so you ask to see a picture. You say, “Aww, he’s a big guy.” (Say the obvious thing.) Add a little more regular back-and-forth. If you’re comfortable, relaxed, and seem to be enjoying the moment, don’t believe the gurus. Basic small talk can work too when it’s delivered right, and when you’re actually curious about her.
It’s cool if you went skydiving last week. But if you have a coin collection you’re fascinated by, there are women who will give you the time of day even if they couldn’t care less about coins. Sorry to go cliché on you, but it’s not what you say, it’s how you say it, and what your body is communicating while you say it. Does that guarantee success? Absolutely not. But what I can guarantee is that if you’re obviously nervous and look like you’d rather be anywhere else, it probably won’t end well.
Her body language is live feedback, and you use it the way you would with anyone: to steer the conversation. You’re not standing there waiting for her to hug you and tell you she’s so glad you came over. You’re paying attention so you can adjust as needed, and you’re deciding a few things yourself.
Is she someone I’d actually like? Am I enjoying this? Is there something here? A guy who’s asking himself those questions isn’t playing validation bingo, and she can feel the difference. This ties right back into the who-is-this-person curiosity loop.
Watch what happens when you bring something up. When a topic lands, you’ll see it: she leans in, her answers get longer, she gets more animated, and she adds things you didn’t ask about. Stay there. When a topic falls flat, you’ll see that too. If you ask about her job and she reflexively makes a face, okay, work’s probably not going well. Find another thread she enjoys more. That’s not placating her. That’s called being a good conversation partner, and not pushing her down a path she’s not interested in talking about. But notice this: you have to be there, present with her in real time.
And if she isn’t energetically laughing at your jokes, that doesn’t mean she hates you either. Nerves go both ways, and a shy woman can be glad you came over and still not ask you much back. If she isn’t giving you clear signs she wants out, carry a little more of the conversation yourself, make your questions easier to answer, and give it a few more minutes. If you still can’t tell, ask for her number. Her answer is the clearest signal you’ll get.
4. Closing, with a number or without one
Ending the conversation is the part where a lot of guys mess up and fumble through. But it’s actually the easiest of the 4 to get right.
If it’s going well, don’t wait for it to run out. Leave while it’s still good, and tie the ask to an actual plan: “I’ve got to get back to work, but I’d definitely like to continue this sometime. How about we grab drinks this weekend?” If she says yes, get her number right there, and then keep it level. There’s nothing to celebrate yet, and “great, I’ll text you this week” is plenty. That goes a lot better than “Can I get your number?” out of nowhere, which makes it sound like you’re collecting them.
If it isn’t going well, or she says no, it’s time to pack up the wagon and bow out gracefully. Say, “No problem, it was really nice meeting you,” and then move on with your day and go find other fish that are biting. That isn’t giving up. Handling a no well is the confident move, because it shows her your confidence never depended on her saying yes.
These 4 steps are the short version of Part II of my book, Nice Guys Can Get the Girl Too. The book gives each one its own chapter, from the approach to the close, and then even adds texting and first dates, which we don’t cover here.
How to get better at this over time
Nobody walks into a gym for the first time and puts 225 on the bench, and nobody should expect to walk up to the most attractive woman in the room the first day they really start trying to improve their dating life. Approaching women is a skill, and it gets built the same way muscle does: by doing a little more than you did last time.
Start where nothing is at stake: the waitress, the mail guy, the barista at Starbucks, the guy next to you at the game. Keep doing that until it’s boring. Then move on to people you’re a little nervous around, and after that to women you’re attracted to in easy settings, like a party where you already share a friend or a class where you’ll see each other again next week.
Check out this article: Most of the 7 best places to meet women are settings that are perfect for these kinds of conversations. Cold approaches, like a stranger in a bookstore with no context at all, come last. Move up a level when the one you’re on stops doing anything to your heart rate. It shouldn’t take you a year to get to approaching the women you want, but a few weeks of warm-up is definitely justifiable.
The no-pressure conversations also help you build social momentum on the day itself. If you’ve already talked to 3 people before you see her, walking over is a much smaller jump than going straight from silence to a woman you’re attracted to.
One habit makes the practice pay off faster. When somebody tells you something about themselves, hang onto it and ask about it the next time you see them. If the guy at the gym mentions his son is starting college, ask how the kid’s settling in when you run into him next week. It costs you nothing, people notice it immediately, and it’s the same thing you’ll be doing when a woman tells you she’s got a show on Friday.
But make sure you don’t just stick to the easy conversations. Chatting with the barista every morning is a perfectly good hobby, but at some point you have to add weight to it.
Okay, it’s time to wrap this up. I hope you found this article helpful. If you remember nothing else, remember these five items below.
- Don’t tell yourself to be confident. Remind yourself to be calm and chill.
- Be present and curious all the way through, from pre-approach to conversation, all the way to the close.
- You can often close with just small talk if you’re doing 1 and 2 well.
- Practice makes perfect, and don’t wait for the pretty girls to practice. Start conversations with everyone.
- Don’t let the What-If Machine take over or just settle for easy conversation. Eventually, you need to just say “screw it” and just go for it.
Readers Also Read
