Should you approach a woman with headphones in? 

To approach a woman with headphones in, or not to approach?

That is the question. ;)

As it is, approaching a woman can be scary for many reasons, even when she doesn’t have headphones in. (!)

So what in the world are you to do when her headphones *are* in, or should you approach her at all in that case?

The dilemma is real.

On one hand, you don’t want to appear rude or aggressive; on the other hand, you don’t want to let a perfectly good opportunity slip through your fingers… for the third time this week (or this afternoon!).


So what do you do?

In this post, we’ll cover whether or not to approach a woman with headphones in.

Then we’ll discuss how to gently give her time to warm up to you so you can approach her in a natural way.

Specifically, we’ll discuss…

  • How can you gauge whether she is open to you?
  • If she looks away from you instead of holding eye contact, what should you make of that?
  • Once she’s open to you, how do you start a conversation?
  • And more…

Let’s dive in!


Whether to Approach a Woman With Headphones In

As a first rule, do not approach a woman while she in that very moment has headphones in, whether she’s on the street, at the gym, at the grocery store, or anywhere.

So what do you do if you still feel drawn to her?

If she has her earbuds in, then eye contact is the best you can do because you can’t really talk to her at that point.

Reason being, she has created a distance between herself and the world by wearing headphones, whether she meant to or not.

Therefore, while you can encourage her to open up, you can’t demand that from her.

If she wants to be approached or talk to, she needs to take her headphones off and remove the barrier she has created.


You can help her by making eye contact…

And then you can gauge whether she is open to you from there.

By making eye contact in the first place, you’re showing her that you find her attractive and that you like her.

If she returns your eye contact, then you can make direct flirtatious eye contact with her so that she feels more compelled to take her headphones out and become open to you.

If she takes her earbuds out and then lingers around you, then she may want to talk to you.


What if she looks away instead of holding eye contact?

Most people don’t hold eye contact for long at all.

Do you want to know why?

It could be (1) that they’re somewhere between not interested and anti-interested.

Or… it could be (2) that they’re shy and it’s vulnerable to have eye contact.

Both are possible.

Even if you see somebody who is the most attractive and the most alluring person you’ve ever seen, it’s still hard to hold eye contact with that person, is it not?

So she may not keep eye contact.

But if she makes eye contact while she also does not seem with her whole vibe and her whole body like she’s actively turning away from you, then she might like you!


3 options if she’s looking away: 

(A) Not interested: Once her headphones are out and she makes eye contact with you, but turns away on purpose and with her vibe, then it’s best not to say anything. That means she doesn’t want to talk with you further.

(B) Interested: And if she does *not* actively turn away from you with her vibe and her body, then she might just be shy. In this case, perhaps she is hoping that you would say something to her. That’s always a possibility when she doesn’t point-blank turn away from you.

(C) Neutral: Alternatively, she may not have thought one way or another about you. But at that point, at least she’s seen you, you’ve seen her, and now it’s easier to say something. She knows that you’re there.

So, you can rest easy that she is somewhere between neutral and hoping that you’ll say something *if* she’s not actively turning away from you.

And at that point of openness on her part, then starting a conversation is taking the next tiny step along the continuum of interaction.


Once she takes her headphones out, you can start a conversation.

The great thing here is that you’re complimenting her simply by starting a conversation.

You’re showing your interest by saying something, but it’s still relaxed because you’re not asking for anything else beyond that.

If you’re at the gym or a place that you have seen her before, you can say,

“Hi, I think I’ve seen you around. I’m so-and-so.”

If you’re on the street or someplace you haven’t seen her before, you can say,

“I noticed you, and I had to come say ‘hi.'”


Perhaps you’re saying, “That’s still scary!”

It’s good to remind yourself here that you’re not trying to start an hour-long conversation.

The length of time y’all talk from there is all going to depend on the connection flowing between the two of you as you talk.

Each of you can decide moment by moment if you want to keep talking or not.

Once she has taken her headphones out and you start a conversation with her, the worst thing that would happen is her responding with something like, “Oh, hi. I’m so-and-so,” while sounding annoyed or awkward that you said something.

So let’s imagine that for a moment.

Then let’s relax because that is the *worst* that can happen. (!!)

And sure, that does feel bad. It does.

But here’s the thing…


You can embrace a small level of gradual risk.

Anytime you start a conversation with someone, you are taking a risk that you might feel bad. That’s true in any situation.

It is always vulnerable to do that because she might not like it, but that’s par for the course. It will happen like that sometimes.

But you can be gradual with it; you don’t have to do everything all at once!


What you can do is work your way up to something bold.

You would really only start a conversation out of literally nowhere only when she’s on her way to somewhere if you felt so compelled (only when her headphones are *not* in).

Otherwise, you would naturally only want to say something if she’s quite open.

For example, she might be more open and not in a hurry (and have more time to take out her headphones out if she’s wearing them) if you’re both in the same place for a while, like at the gym or the grocery store.

Here’s another helpful tip:


Be aware of opportunities that are easier and more natural.

For example, perhaps you’re both using the same weight rack at the gym or looking at the same heirloom tomatoes at the farmers’ market.

If you’re already nearby and you’re sharing a space in common, then starting a conversation is much easier and more gentle compared to if she’s walking somewhere on a mission.

To talk to her while she’s walking with purpose would be much bolder. It’s not that you can’t do it, but it’s harder to do it and it’s more risky.

On the other hand, if you’re both already sharing the same workout space or perusing the same farmers’ market stand, then it’s way less risky.

In fact, it’s not even really that risky at all if you’re making eye contact with each other.


What if you don’t have a chance to make eye contact at all?

Eye contact is not going to happen naturally in every case.

If she does *not* have her headphones in, then you do *not* need to make eye contact first; it simply makes things a little easier.

And it helps her to not be surprised, which is nice.

Along those lines, get in her line of sight first before speaking to her; don’t speak to her from behind because it’s a bit (or a lot) jarring, as you can imagine! Similarly, touching her is a definite no if she hasn’t even seen you.




From making eye contact and thereby encouraging her to remove her earbuds, to gauging her interest level, to offering a conversation starter if she seem open to that, we’ve covered a lot of ground!

Hopefully, you feel more comfortable inviting a woman who is wearing earbuds to connect with you.

Gone are the days when you beat yourself up for not saying something. Now you know the sequence of events that must take place (her taking the earbuds out and not turning away from you) *before* you can reasonably start a conversation with her.


Need more support?

If you’d like more support to approach a woman with headphones in or anytime for that matter, then great!

  • You can get started with our ebook on finding your own unique vibe to build your base level of confidence, which will help you feel stronger in the moment as you see a woman who you’d like to approach.
  • You can then explore Launch Your Dating Life, which is our comprehensive solution for developing a thriving love life based on bringing out your best self. Apply at the bottom of that page to speak with an attentive, supportive member of our team about it!

Also, have you seen our other posts on how to tell if she wants you to talk to her or on starting a conversation with a beautiful woman? Those have tons of helpful tips and guides for you as well!

Thanks for reading, and reach out if you need anything. We’re at :)

Sarah from IA
Sarah from IA
Sarah is founder and CEO of Introverted Alpha; the top dating coaching company for introverted men; featured by Forbes, Business Insider, Cosmo, and more. Pick up your free copy of Introverted Alpha's 22-page ebook in the box below.

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