When and How To Approach Women: It's Not as Hard as You Think

He's approaching women without being creepy
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This is a topic that comes up often with my guy friends and one I find so interesting. If you’re like my friends and wondering how to approach women and when, settle in and get comfortable.

I’m going to strip away all the nonsense and give you some simple advice. No ridiculous promises or “lines that are guaranteed to work on any woman” because there’s no such thing. Just simple advice for you to follow — this topic isn’t as complicated as our minds make it out to be.

When to Approach Women

First things first, let’s talk about when to approach women you're into. If you’ve read other articles on the topic, you’ve probably been given a long list of dos and don’ts here. You can go ahead and throw all those notes out.

The one and only rule is to do it when she isn’t obviously busy. If she has her headphones on and is mid-set at the gym, that’s not the time. Likewise, if she’s clearly in the middle of a meeting at the coffee shop, save it for another day.

So long as you aren’t interrupting something important, just use your common sense and go for it. It’s no more complicated than that.

How to Approach Women No Matter Where You Are

So you’ve seen someone you’re attracted to and you want to say hi. Now what? If you’re thinking this is the part where it gets complicated, that’s because you’ve been watching too many “pickup artist” clips.

Here’s a strict rule you can apply to every part of your dating life: Ignore advice from “pickup artists.” The amount of cringe that comes from that community is something you want to distance yourself from. Let’s talk about what you can be doing instead.

This isn’t a game — you don’t need “tactics”

Picture this: You walk up to a woman, you say hi to her and she turns out to be a fellow human being. It’s a crazy concept but one these “artists” seem to have forgotten. You don’t need to “game” her or develop a complex strategy, just go and say hi!

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When you approach women you don't need pickup lines, ever

So many guys approach girls at a club and fall flat once they utter a cheesy pickup line. They’re not cute and they’re not funny. If she laughs at them, she’s either very drunk or giving you a pity laugh. Not a great start.

If you feel more comfortable using the same sentence each time to start a conversation, that’s okay. There’s a difference between saying “Hi, I’m Joe. I noticed you when I walked in and wanted to introduce myself” each time and “Hey baby, are you a bank loan? Because you got my interest.”

Ugh, gross!

No need to hide your intentions during the approach

Dated social norms might make you feel like you need to mask your intentions for now. To chat about something else arbitrarily and see if the two of you get along. That can be a great way to meet friends, but that’s not what we’re looking for here, right?

Especially if you’ve approached her at a bar, she already knows why you’ve come over. If you say hi then pretend you just want to talk, it's clear that you aren’t being genuine.

It’s so attractive and refreshing when a guy approaches and openly says it’s because he’s attracted to me — So long as he’s not being crass or sleazy anyway.

Be forward, be flirty and pay attention to how she responds. Simple.

How to approach women with genuine compliments

Everyone loves to receive a compliment. The ones that have the most impact are genuine and focus on something we can control.

Rather than a generic “you’re so hot,” focus on something specific to her. It doesn’t have to be something big, it can be as simple as complimenting her drink choice.

As you get to know her, be open about other things you appreciate along the way as well. For now though, you don’t have much to work with and if her eyes really are amazing, you’re not the first person to tell her this week.

Don’t decide she isn’t interested before you even say hi

It’s normal to feel nervous about approaching women and that’s okay. Those nerves can make us catastrophize the whole thing, coming up with a long list of reasons why she'll reject you.

  • She’s too busy
  • She’s with her friends
  • I’m too short
  • I’m too tall
  • I’m too fat
  • I’m too skinny
  • I’m not attractive enough
  • She has a partner
  • Mercury is in retrograde

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The list goes on. While any one of these could be true — maybe not the last one — you can’t possibly know that until you try.

Unless she’s clearly busy with something important, meeting someone new might be just what she needs to brighten her day. She isn’t “too busy” with her grocery shopping. She isn’t immune to meeting a confident guy just because she has friends with her.

If she isn’t into you or now isn’t the right time, you’ll find out for sure when she tells you politely. As long as you’re respectful with how you approach girls, most of them will be incredibly nice about saying no if that’s the outcome.

For the handful of women who aren’t, this is also a good thing. It shows that you dodged a bullet. You’re better than the type of woman who gets a kick out of mistreating others.

You miss 100% of the chances you don’t take

I know, I know, it’s so cliche. Even so, this is something to remind yourself of any time you’re talking yourself out of it.

Your chances of at least having a good conversation when you approach are a lot higher than you think. Even if we push those chances way down to 50%, that’s still infinitely better than the 0% chance you have when you just walk away.

Put it this way, how many times have you gone on a date with someone after just looking at them from a distance? How many girls have you had a crush on and never approached them in college? I can assure you it’s not a very effective strategy.

The worst-case scenario is that you end up back in the same place you were before you started. Don’t reject yourself on her behalf!

The outcome from approaching a woman doesn’t define you

Especially when you’re nervous, it’s normal to feel tied to the outcome of your approach. As though you’re a better person if she’s interested or “not good enough” if it doesn’t work out with that particular woman.

Think about walking along a busy downtown street. Are you interested in every single woman that walks by? Of course not. Does that mean those you aren’t interested in are inferior? Absolutely not.

We all have our own preferences and lead complex lives. Sometimes it might even be that we’re at a complicated point in life and dating isn’t on the cards.

One person lacking interest doesn’t mean you aren’t good enough. Rejection won’t change your life when you try to pick up women. Really, it won’t even change your day unless you focus on it!

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There’s a reason women can’t agree on “rules” to give you

If you’ve read articles with strict rules you “have to follow to be successful when you approach women" you’ll notice they tend to contradict each other.

You should always approach at the gym. . . but you should also never approach at the gym.

It’s best if you approach through the day. . . but approaching women at night is best.

Start by talking to her friends. . . but also just focus on the person you like.

Or if you don't feel like chatting with everyone, why not just keep your eyes open for girls who want to be approached?

This is because every woman, every human is different. We all have our own preferences, personality types and quirks. You can’t apply a single set of rules to every approach and expect it to go the same each time.

That’s why almost everything here is about you, not her. It’s about how you think about your approach and portraying yourself in the right light.


Like so many things in dating, the best way to get comfortable with approaching women is to get out there and do it. These tips should help you along your way but no amount of reading can give you experience.

The next time you see someone you’re into, just go and say hi. Even if you have a 30-second conversation then leave, you’ve just made it past the hardest part. Everything gets easier from there.

Good luck!

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