Over the past couple of weeks, there's been this really cute girl who sits near me inside a coffee shop, which has a cozy, "productive" vibe to it -- everyone's doing work on their laptops. I want to start a conversation with this girl, but there's one significant obstacle: she's always wearing her headphones.

So, my question is:

How can I effectively and politely start a conversation with this girl who's sitting next to me and wearing headphones?

We've seen each other - and smiled at each other - for a few weeks now. The vibes feel pretty good, but her wearing the headphones makes it tricky to say "hello" to her.

The location: Manhattan, New York, United States.

  • 8
    Please don’t write answers in comments. It bypasses our quality measures by not having voting (both up and down) available on comments, as well as having other problems detailed on meta. Comments are for clarifying and improving the question; please don’t use them for other purposes
    – sphennings
    Commented Feb 28, 2018 at 4:12
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    Have you said "hi" to each other? I assume either one of you is already there when the other comes in. If you are in before her, when does she put on her headset? Commented Feb 28, 2018 at 13:43
  • 1
    In case anyone's wondering why this post got locked, you might want to read this interesting meta answer on why Q&As about picking up are not a good fit for IPS.
    – avazula
    Commented Oct 1, 2019 at 7:45

18 Answers 18


You don't.

You're asking how to interrupt someone who's working with mostly-inconsequential personal matters. If someone did that to me, I'd be annoyed at their lack of situational awareness, and would be looking to end the interaction quickly and get back to work. There is no way to do this that is polite and respectful - at risk of sounding like a broken record, you're potentially breaking her working "zone" for something totally unrelated.

As far as I'm concerned, if someone's giving out signals that they're working and/or don't want to be interrupted (and headphones are a strong signal on that axis), then the only time you interrupt them is to let them know the building's burning down around them.

I may exaggerate slightly.

Instead, why not...

...strike up a conversation when she's not wearing the headphones - or at least when she's not working. The obvious point for this at a coffee shop would be while she's ordering - even if she's still wearing headphones at that point, she's also clearly not working, so you're not interrupting or breaking her flow. If the conversation you strike is interesting, then you might end up continuing it over your respective coffees - but also be prepared for her to say "that's nice but I'd rather get on with my work", and respect that.

  • 1
    Comments are not for extended discussion; this conversation has been moved to chat.
    – HDE 226868
    Commented Feb 28, 2018 at 1:00

You are looking for a breadth of answers, from which I read that you hope to find one which doesn’t advise you to leave her alone. If you do get such an answer I’d like you to think about this before accepting it:

there's one significant obstacle: she's always wearing her headphones.

She isn’t wearing them by accident, they are an obstacle she had deliberately placed between herself and random strangers.

However much you wish it was otherwise, you are a random stranger. The obstacle is not a challenge for would-be-swains to overcome, it is both a defence and a big sign saying ‘I am not open to interacting with people in this situation’.

The defences are against you as much as they are against anyone, the sign is not somehow only for other people. You are being asked and encouraged to leave her alone.

If this was going to be your meet cute with Cappuccino Girl, if she wanted to strike up that conversation, she’d have taken off her headphones by now, or she wouldn’t always already have them on when she/you sat down.

In shared public places, we all have to accept out personal space being reduced and our individual bubbles getting squashed against other people’s. It is highly likely that she doesn’t see sharing a smile with another coffee-shop regular as anything other than acknowledging the sharing of space. If it was an invitation to chat she would take off her headphones. Keeping them on is her defining her space. Invading her space is an aggressive move even if you don’t think so.

Please let her be. Don’t be creepy coffee-shop guy.

If you must try something, try not smiling at her for a few days. If she misses your interaction she might speak to you first.

When all the advice you’ve already had is to leave her alone, persisting in looking for a different answer is already making you look situationally tone-deaf and giving off those creepy coffee-shop guy vibes.


Model the behavior you're seeking and see if she follows.

Wear a set of headphones next time you go.

When you make eye contact with her and she smiles back, stay right where you are and take your headphones off to indicate that you're willing to interrupt your work to talk with her.

If she reciprocates, then you have your chance. If she does take off her headphones from this approach, keep this chat brief unless she seems obviously eager to continue. Start with something complicated like "Hi. My name is {say your first name}" Measure her response. Everything you say after that is on you.

If you try and she doesn't take her headphones off, move on.

  • 6
    ...one thing to add that might be missed. Make sure you are wearing your headphones before you see her. Definitely make sure you don't put the headphones on as you notice her. If she likes you, she may take that as the same "dont talk to me" nonverbal cue that others seem to be primarily focusing on. Commented Mar 2, 2018 at 16:54

You can't do it politely

There is no way to strike up a conversation with a stranger working with headphones in that isn't incredibly impolite. A good boss should think twice about disrupting an employee with their headphones in. What reason does a stranger have to impose on someone like that?

They're wearing headphones to isolate them from the world and trying to get work done. No-one wants to be interrupted in the middle of their work day.

Headphones are a clear indicator that they want to be separated from the rest of the world and not disturbed. By ignoring this very obvious boundary you are signaling that either you are so imperceptive of others that you can't see that they don't want to talk to you, or you're so inconsiderate that the fact that they don't want to talk to you doesn't matter. These are both poor options the only good option is the leave them alone to get their work done in peace.

When this question was proposed in chat a month ago people responded by saying:

Seriously I wish more people would understand that if I am reading or wearing headphones or what have you...i don't wanna be interrupted.

I don't care how great you think I am or how cute you find me, I have made it obvious I am distancing myself from interaction, respect that.

Unless the bus/coffee shop/library is on fire/about to explode/flooding/at risk of tornado... etc...

Trust me on this one. It's rude and invasive and bypasses any idea of respectful boundaries.

The headphones are the fuck off vibe, friend

No positive comments could be found in chat regarding this question.


Don't. Girls often wear headphones even when they aren't listening to music, just because they want to be left alone.

I'd suggest that you draw a cute comic/write your number on on a piece of paper and send it to her. Then wait and see if the rejects you or responds.

Or wait until she isn't wearing headphones.

Tbh, she probably isn't interested in you, so be prepared for rejection and don't look like a stalker by repeatedly trying to strike up a conversation with her

  • 2
    I might add: drawing a cute, quirky little note as a fun and open–ended invitation is a clever idea — but it doesn't really work if someone isn't comfortable with such a persona. Commented Mar 5, 2018 at 17:18
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    Did you mean to write "[People] often wear headphones even when they aren't listening to music, just because they want to be left alone."? ;)
    – ANeves
    Commented Mar 7, 2018 at 17:04

Generally, I would agree with the suggestions that you shouldn't try to talk to her.

I would also avoid being too direct - buying her a drink or handing her a note puts an obligation on her to respond and is also quite a dramatic escalation of interaction between you if you've only previously acknowledged each other with a smile.

Having said that, there is a more subtle way to non-verbally 'step up' the communication: If you see her regularly and feel that she's likely to recognise you then you could wave hello to her next time. This shows familiarity and friendliness (a step up from just a smile) but still gives her the opportunity to choose whether she responds in kind without it being too confrontational.

If she wants to have a conversation, this could also be an opening for her to remove her headphones.

  • 5
    Yes, this. Take the opportunity to wave hello which is a non-verbal 'step up' and leave the ball in her court. Not impolite, not forceful, if she doesn't rise to it then just smile and say nothing from then on. Or maybe give her a parting smile and wave and see if she changes routine next time.
    – kleineg
    Commented Feb 28, 2018 at 22:46
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    Cheers to this answer. To me, it's the only sensible way to try to communicate with her. It may be that saying hello some times leads to her not wearing headphones anymore, signalling she's open to chat. Commented Mar 1, 2018 at 9:35

You don't. Not only that, you discourage anyone else from doing so either.

The most important thing to understand here is this: You do not have a right to attempt a romantic relationship with every random woman that happens to strikes your fancy out in the world. This shouldn't have to be said, but the preponderance of evidence shows it clearly does. There's a famous video showing excerpts of 10 hours a woman spent walking around NYC, with over 100 attempts to do everything from initiate conversations to out and out harassment. That's over 10 an hour!

Women should not have to put up with this.

Furthermore, one of the most common ways to try to avoid this kind of contact is to wear headphones. So if you see a woman out and about wearing headphones, consider it code for "Please do not talk to me."

There's even an article on this exact subject on Upworthy titled, get this, Advice for Talking to Women Wearing Headphones Ignores Why Women Wear Headphones.

If there's really some kind of connection there, she will take off her headphones on her own. If she doesn't do that, please leave her be.

  • 4
    One interesting find from that Wikipedia link: This is a documented issue in NYC, perhaps not coincidentally where the OP hails from. In many other cities around the world where this same test was tried, the men of the city did not feel entitled to behave this way.
    – T.E.D.
    Commented Mar 1, 2018 at 14:58
  • +1 I agree with your answer, but having looked at that video, I'm of the opinion there was a different agenda at play. Included in the 100 attempts (in addition to as you say, attempts to initiate conversation and out and out harassment) were dozens of simple 'hello', 'hi ma'am' and 'good day' type comments where the people made no follow up attempts to keep talking, they were simply being polite.
    – mcalex
    Commented Mar 7, 2018 at 7:20
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    @mcalex - I believe the issues around those kind of selective greetings to complete strangers are gone into detail on in much better forums than this for that kind of discussion, so I'd rather not see it reargued here. Suffice to say either way those are completely relevant here, because the topic happens to be guy wanting to initiate exactly that kind of "friendly" contact with a person who has not invited it.
    – T.E.D.
    Commented Mar 7, 2018 at 15:09

Most answers say "don't", and they are not wrong. But OP mentions

We've seen each other - and smiled at each other - for a few weeks now. The vibes feel pretty good,

I'd like to provide a "do" answer, backed by my personal experience.

Some day, I was in a happy mood and smiled at many strangers while commuting. One girl caught my eye because she smiled back genuinely. You could have interpreted the rest of her behaviour as discouraging: She sat quite far away in the train, was wearing headphones, only made eye contact few times. So I left her alone.
Over the next half year, we happened to see each other again while commuting. Always quite far away from each other, but always she would smile back or even be the first to smile at me. I started wondering if she's one of the few people who smile back or if I might even know her and don't remember her. So I went to ask.
The moment I walked up to her, she ripped her headphones out, gave me her hand and told me her name.

From this experience, I argue that it's always worth a try if "the vibes feel pretty good". However, make sure you're not creepy:

  • Don't corner her. I chatted her up at the train station, so she could easily have just walked away into a different wagon.
  • Make sure she sees you coming so she is not surprised.
  • Have some reason why you talk to her. She might not have meant smiling as a signal, just as being polite. If this is the case, she would possibly be confused what you want from her.

Maybe it's a cultural thing that most answers say "don't", but I've had also a few other conversations with (mostly female) other passengers that they seemed to have enjoyed as well. Usually though, they just happened - e.g. because I was unsure where the tram was going and thus asked the girl next to me (even though again, she was wearing headphones).

Just make sure to look at other signs as well though. Headphones alone just mean she prefers listening to music. She can still take them out if she wants to. Conversely, they could also be there because she doesn't like to talk.
Does she smile? Does she look too tired to have a conversation? Is she being productive and probably doesn't want to be disturbed? Etc.

As you say that she seems productive, make sure to give her an easy way out. Maybe just ask her if she'd like to talk or prefer to not be disturbed. You can then back out, maybe offer her to chat you up next time if she feels like it.

  • 1
    I'm with this one. The only way out of your misery is to make the approach. Tap her on the shoulder go "Hi Hi. I can't stop thinking about you. I mentioned you to some people online and there's like a million, maybe two million, of them telling me to leave you alone but I can't let this opportunity to meet you slip away." If it works that's great. If it doesn't then you're free to get back to work. Happy Day, Commented Mar 2, 2018 at 13:22
  • 17
    I would advise against tapping on the shoulder unless she doesn't hear the hi through the headphones. Also, I don't know if it's just me but I would consider the phrase you offer as creepy @StephenBosten
    – lucidbrot
    Commented Mar 2, 2018 at 16:24

If you feel that leaving her a note is too aggressive, the next time your eyes meet do the following:

  • Make a motion that looks like removing the headphones.
  • Cock your head to the side (or raise your eyebrows, that sort of thing).

At least in the US, that should be pretty clear body language that you're wondering if she'll remove her headphones, the implication being you want to talk.

If she shakes her head or ignores you, just smile and go back to your laptop. Do not be a creep - you took your shot and she doesn't want to be bothered. If she changes her mind in the future, she knows you're interested and she'll initiate the conversation.

  • 35
    As a man, this would annoy me. I would think you had a somewhat important question to ask me. The implication to me is not just that they want "to chat". In general wearing two headphones is a sign that you don't want to "just chat". Also, if you do take them off expecting a question and they just start chatting, it's really hard (IMO) to break off the conversation without feeling rude or cold.
    – JMac
    Commented Feb 28, 2018 at 13:06
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    My problem with this pantomime approach is that it serves as communication with her before actually receiving a signal that she wants to communicate. That and the motion is going to make you look like a douche if she responds back with a cross eyed look. The goal here is to initiate a conversation without imposing. Either a note or a signal to "hey, take your headphones off" are the same thing here. For a woman whose guard actually is up, the suggestion is tantamount to "hey. I need you to take down your guard" and any way you slice it, any direct request for this is going to be impolite. Commented Mar 2, 2018 at 13:08
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    I wouldn't be so forward as to mime removing headphones as it looks like you have something important to say. But smiling, maintaining friendly eye contact until she looks away, and raising the eyebrows clearly indicates friendliness and willingness to engage if she's interested. At that point she'll probably smile and either go back to her thing or take her headphones out. Commented Mar 2, 2018 at 18:29
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    @JMac As a woman, this would annoy me for the exact same reasons you've stated. I would likely take off the headphones (especially in New York) just because I assume coffee-shop-guy has something somewhat important to ask and then be stuck having to find a way to end the 'conversation' he started without either leaving him thinking I'm interested or bruising his ego.
    – user61524
    Commented Mar 6, 2018 at 7:15

Don't really know if this would be a good answer, but as an old-school guy what I would do is this:

You say you have seen her for a couple weeks, so if you haven't paid attention of what she usually orders, check that and order something for her (e.g. if she orders a coffee and sometimes a slice of pie, one time when she only orders the coffee you order the slice of pie and send it to her table); make sure the waiter or whoever delivers tells her that it comes from you and watch her reaction: if she looks upset or annoyed, you had zero chances from the beggining. Otherwise, you have opened a chance for interaction.

Now, be aware that she can be genuinely busy, and she might not talk to you or let you sit with her immediatly, but she might talk to you when she leaves. Still, she reacting positively gives you open card to at least wave at her and say "hello" the next time you see her.

Good luck, but be patient: stalking to her or being overly insisting is never an option.

  • 11
    This is obviously one possibility but I think it puts the girl in a more difficult situation as if he would just try to talk to her. If she likes him all is fine. But if she is not interested how should she react? Eat and ignore him? Don't eat it? Tell the waiter she does not want it? This makes it more complicated for her to not accept his invitation in my view.
    – user8838
    Commented Feb 28, 2018 at 3:44
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    I understand this tradition, but with a modern view this looks like manipulation. Giving an unexpected gift creates an emotional obligation to reciprocate, and if she's not interested it's now gotten awkward. It is also playing into old stereotypes of men as the provider.
    – O'Rooney
    Commented Mar 5, 2018 at 21:50

There's no way to try to talk to her without risking annoying her or being perceived as rude.

However, life is full of risks and inaction will probably just lead to her playing on your mind for weeks on end before something happens and your chance is gone for good. So instead of 'no', I'm going to say don't do nothing.

There's a very simple thing you can do to discover if she is interested in striking up some kind of rapport, but be prepared to accept that she might not want to.

  1. Make sure you don't have a drink.
  2. Wait until she's finished her coffee
  3. Go over to her and wave (or do some other gesture) to get her attention
  4. Tell her that you were about to get a coffee and ask her if she'd like you to get her one since you're getting up

If she says no, just go get a coffee for yourself, then forget about her and move on.

If she says yes, buy both your cofee and her coffee, bring her coffee to her and then go back to your seat and get back to what you're doing. If she offers to pay or wonders why you did it then say you 'just felt like being neighbourly' or 'just felt felt like doing a good deed'.

If she's interested in having a conversation or becoming friends she'll probably talk to you or return the favour in the following days and you can take it from there.

If she doesn't attempt to make conversation or return the favour in the next few days, just forget about her and move on. (Possibly even move away from her if it helps.)

It might seem hard to let go, but remember that you don't actually know her, until you've spoken to her and got to know her anything you think you know about her is just a story in your head. (Also there's not exactly a shortage of humans, if she's not interested you'll find another one.)

In summary, the worst case scenario is that she's not interested, but it's better to be reasonably sure than to assume and never really be sure or to sit there wondering until it's too late.

Even if she does want to become acquainted, please remember that's still a long way from being ready for a relationship. It might be the case that she'll only ever want to be friends or that she's happy to exchange coffee purchases now and again but doesn't want to become more familiar than that, in which case you either have to accept that or move on. I honestly hope it goes amicably, but you should always be prepared for the worst case scenario, which in this case means letting go.

Lastly, I acknowledge that there are some flaws in this.

For example, she might refuse a drink because she might think you're going to spike it with drugs or something. (Though if that's the case then you'd probably have had a tough time getting to know her though other means anyway.)

Trying to make contact with strangers is almost always going to have its difficulties. Generally easier to meet people through things like clubs, where you're expected to talk to each other and are likely to have a common interest.


As others have said, she probably doesn't want to be interacted with. That's usually the end of the line. "You don't" is usually the correct answer, as previously stated. But if you got some good vibes, you could risk giving her a visual non-invasive cue, like a note.

(more on the non-invasiveness on my first edit point at the end of the answer)

What would I do?

The operation

(cue Ocean Eleven's Music)

Next time I leave the coffee shop before her, just as I pass by her table, I would leave a post-it-sized piece of paper with a QR code and then smoothly leave the shop without even turning around.

I wouldn't wait for a response or make a big deal out of it. She will probably notice it's you who left the note (unless it's really crowded, people tend to notice other people approaching their table). If she makes eye contact in your way pass her table, just send her a slight smile (I said slight, don't overdo it!)

The QR code will surely arise her curiosity, she will visit it and then...

The aftermath

...then she either finds it very cute or very creepy.

  • If it's the first, now the ball is in her roof and she will initiate contact with you or give you a very explicit signal.

  • If you never see her again or she never makes eye contact with you again... well, then it's the second and you should never try to contact or stare at her again... sorry! It was not meant to be, or you shouldn't have try this. Serves you right, taking random advices from the internet. In any case, Game Over.

Wait, what about the link?

Generating a QR code is really easy. You can make it link to any URL or show any text message

You can make the QR link to something like a picture (cute/funny hand-made drawings are usually big winners!), a tweet, or a message. Don't overthink it. Make it simple. Make it clean. Make it sympathizing or cute, but over all, make it accurately reflect your personality, since this may be the only thing she has to judge you by.

(My example links above are not the best, I just briefly skimmed the internet. )

In my case, since I'm usually funny, upfront, and very meta, it would probably be a link to this question. This has the potential to be interpreted either as extremely cute or creepy, but I was never one for half measures! YMMV

EDIT addressing comments and other clarifications I deem appropiate:

  1. The idea behind using a note instead of something like starting a conversation is that is an asynchronous interaction. Meaning that the girl has the private choice to follow up on the interaction or not, however she wants, whenever she wants. She could see the link and ignore it, she could take it home and think about it, she could bin it or leave it on the table without even looking at it. And you're not there to see what happens, which takes a lot of pressure from her! With a synchronous interaction (like trying to start a conversation or paying her coffee), she has the pressure to decide and react somehow in that moment. Maybe she wants to think about it before. Maybe she doesn't want to react at all.

  2. This answer is very aware of it's potential creepiness. There are a few people out there that will find this fun. That people would, probably, meet like-minded people. This answer is for those. In my experience, this approach has succeeded more times that it has failed. I've met wonderful people; I met a couple of boring persons, and I possibly have miss out a few great people I would have missed out anyways since I couldn't find a better way to approach and then I'd rather not do anything at all.

    • If you find this approach weird, creepy or stupid, worry not! There is nothing wrong with you! You're probably actually an incredibly sane and nice person who I'd be sorry to accidentally creep out! If I did (or something reading this did), sorry! It was an accident with a good heart!

    • If you find it fun and like the kind of thing you would like to receive, go ahead and try it! (Or not! I want no liability...) It can make for a fun story to tell!

  • 4
    Some random hands me a QR code in a coffee shop, no way I'm visiting it.The best I'd assume is a rick roll, the worst a dick pic.
    – user9837
    Commented Mar 7, 2018 at 11:16
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    @Spagirl That's ok! It's a very possible and acceptable outcome! Nevertheless, you're not just "some random" handing flyers on the street; according to OP, they've crossed looks and smiles. It's not a meaningful bond, but it's.. something. You've seen each other in the same place multiple times. The way I see it, if she doesn't trust you by now enough to visit a link, I don't think trying to initiate a conversation would go much better!
    – xDaizu
    Commented Mar 7, 2018 at 11:29
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    @xDaizu crossing looks doesn't mean anything, I tend to occasionally look at strangers who stare at me just to see if they're staring at me.
    – ave
    Commented Mar 7, 2018 at 13:52
  • @Ave I know it doesn't mean anything, that's why I said it's not a meaningful bond, meaning it's not a bond of any type. But it's a step above a random stranger on the street. On a very long stair. So long that the baker you buy bread from twice a month is like 30 steps higher.
    – xDaizu
    Commented Mar 7, 2018 at 15:21

I don't understand the answers here that say "Don't". It's entirely possible to strike a conversation with a stranger with headphones in a relatively polite way.

You have seen her for weeks and are exchanging smiles with each other. There are a number of concerns when approaching girls in particular:

  • Girls are approached by a lot of creeps.
  • Girls are (as a whole) harassed a lot.

Both of these things are unacceptable, but they are what we have to deal with at the moment.

You basically need to approach her in a way that doesn't violate her feeling of personal safety. If you've created an uncomfortable situation for her then you've lost.

How will you know if she's feeling safe and comfortable? Mostly body language, social context and general vibe of the situation. Smiling is typically a very good sign.

Ideally, you should make yourself approachable to her in a way that lets her easily "signal" that she is interested in communication rather than force a conversation with her.

  • 5
    Would you consider headphone wearing a signal that they aren't open for conversation with strangers?
    – sphennings
    Commented Mar 1, 2018 at 15:16
  • 4
    @sphennings not only I would typically consider it as one, I wear headphones myself sometimes to avoid conversations. That said, the actual cue is a lot more subtle than that - if I'm smiling towards someone in a cafe that I've seen tens of times while wearing headphones, I would personally be OK with interaction. Commented Mar 1, 2018 at 15:19
  • 1
    I would suggest a definition of harassment includes attempting to make conversation with someone whilst a clear sign of wanting to avoid conversation with strangers is in place. And, as you say harassment is unacceptable.
    – mcalex
    Commented Mar 6, 2018 at 16:31
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    @mcalex I'm not sure I can elaborate further than my last comment but I'll try. If someone wears headphones but smiles at you when you see them (for weeks) - that someone might be interested in discussion with you but not discussion with people generally. The actual cues are more nuanced though (body language, context, vibe, etc). Harassment is defined by the person being harassed - which is why this is not a "one size fits all" situation - some people might feel harassed when being approached without headphones (I feel that way sometimes, when approached by certain people). Commented Mar 6, 2018 at 16:57
  • 2
    @mcalex Harassment is typically defined as unwanted or aggressive behavior that, specifically, is repeated.
    – TylerH
    Commented Mar 9, 2018 at 16:46

So, my advice is, like many others, leave her a note. Or, be a little more clever and leave her something like the picture below in a message screen or a note taking app so she can respond, and see how she acts. Put the phone on her desk as you walk by, sit back down, and when she looks at you, smile back like you always have. I did this in a quiet library with a lot of people, and it started the conversation, plus she said it was really cute. Nobody else cared. It also gave her control to start or stop the conversation.

Screenshot of messaging app with message: "Hi! My name is (insert your name here)  What's yours? Btw, cute headphones! :)"

  • Hi, megaplex2112. I removed the questions from your answer; they should be posted as comments on the question - not along with your answer.
    – HDE 226868
    Commented Mar 15, 2018 at 13:23

Go gradually, go smoothly

Girl is wearing headphones, maybe she wants to avoid those around her, and maybe she is just shy and could be love of your life :) You will never know until you try, but don't overdo it . Move trough these steps.

  1. Next time you see her, just slightly nod your head in her direction and smile discreetly. Then continue doing what are you doing. Of course, make sure she sees your greeting :)

  2. If she nods you back or makes some similar gesture, after few days greet her by raising your hand, again casually and again just continue with your own business.

  3. If she doesn't greet you back then do not push it, she is not interested. But if she does, try this little trick . Get some food in a paper bag, appear like you eating and while you greet her, casually offer her. She would likely refuse, but in doing so she would have to talk to you and she would probably remove her headphones, to hear what you have to say. Use this opportunity to introduce yourself "Btw, I'm D. " . She would likely tell you her name. Again do not bother her, continue with your own thing.

  4. Finally, if everything goes well, you could great her using her own name when you meet her next time "Hi, Jane Doe". Again, she would likely remove her headphones for a while, and you could use this opportunity for small conversation (few sentences) . After that, it is all up to you .


I'm going to go on against the grain and propose the following solution to your conundrum:

Just do it

Seriously, that's the only real answer. You can talk to her directly, pass a QR code with a link to this post, give out your business card or go with any other creative reason suggested in this post. There's a 99% chance it won't pan out, but that's okay too. Once you do it your mind will free up and you'll be able to focus on other things in the coffee shop, such as drinking your coffee.

It won't be particularly polite (approaching strangers rarely is), but that's just a trade off you have to make as a single person.

  • 3
    Might be OK for you, but not for the girl who is going to have to worry about another creepy dude leering at her at the cafe, where she has headphones on clearly indicating she didn't come there to talk to people. She is possibly going to be driven away from one of her favorite spots, to avoid her new stalker. This is not "OK" in my book. Leave her the f*ck alone.
    – J. Taylor
    Commented Mar 7, 2018 at 1:19
  • @JTaylor things are often simpler in real life than they are when discussed online. This is one of them. I assure you unfamiliar people talk to each other in Manhattan all the time and OPs impoliteness won't do any harm :) Commented Mar 7, 2018 at 17:51
  • 2
    I never told the OP not to talk to unfamiliar people. I said not to harass women who have headphones on and clearly don't want to talk to him, just because he finds her "cute".
    – J. Taylor
    Commented Mar 8, 2018 at 0:32
  • 2
    No, it's a big deal to a lot of women in NYC, especially since the creepy harassing behavior is often followed by violence upon rejection or refusal to interact: youtube.com/watch?v=b1XGPvbWn0A
    – J. Taylor
    Commented Mar 8, 2018 at 0:44
  • 1
    Negative vibes like she's wearing headphones?
    – mcalex
    Commented Mar 8, 2018 at 9:57

In most societies (even America) a business card with a personal note on the back is not considered inappropriate.

Perhaps, a (legibly) handwritten note to the effect of:

I would be interested in striking up a conversation with you when you are not busy. (signed with your first name)

The business card gives the person of interest information (preferably legitimate, please note) about you. This information will hopefully demonstrate your sincerity, and also that you are a (theoretically) normal person with an actual job. It is also a gesture of trust as you are entrusting the person with real, actual contact information of yours.

It also conveys that your interest is personal in nature, via the handwritten note and you might get bonus points if you have nice handwriting. Furthermore, you are respecting the headphones, and not trying to talk or get the person to take them off.

In some cultures, it is better to offer or place the card with both hands (usually Asian). As they are likely to be busy, placing it on the table within view and reach, but not in their personal space bubble, should be considered. Showing both sides as you place it down can also be considered a politeness, as well as demonstrating that you've written something on the back.

How they treat the card should be a fairly clear indicator of your next step.

Respect their choice and decision.

  • 7
    In most societies? You're going to need some evidence of that. Giving someone a business card is rare even in situations where it is definitely appropriate, in many societies. Doing it as an icebreaker for personal reasons even less.
    – Nij
    Commented Mar 3, 2018 at 22:59

Of course it can be done, but do not ignore the top answers. They are right in that the headphones are an intentional barrier. If she were very much interested in you, she would have used one of those smiling moments to remove them and show you that she is available for talking.

But - you can still be both respectful of her barrier and initiate a closer contact. By now you probably know what she usually drinks and how much of it. Wait until you think hers will be over within the next minutes, then go and order one. Put it on her table, just within her reach, without saying anything and calmly walk back to your table and continue your own work.

You are respecting her boundaries, both the headphones - by not talking to her - and the physical zone by reaching in just enough to deposit the coffee and by leaving immediately after you did that, giving her the space back.

The ball is now in her court. Courtesy requires her to at least say "thank you". The way she does that will tell you how interested she is in you. If he keeps the headphones on (i.e. the barrier up), that occasional exchange of smiles is all she wants and you read the chemistry wrong. If she takes the headphones off to thank you, you can initiate a conversation. If she puts her stuff down and joins you at your table, you should cancel your plans for the evening.

  • 9
    I wouldn't recommend this. It may be fine if she does like you, but equally could come across as creepy (because you're a relative stranger who has paid enough attention to learn to her order), overbearing (because you've put her in a position of owing you something - even if it's just a 'thanks') or even just assumptive (because maybe she didn't want another drink, or she was going to have something different next time). Commented Feb 28, 2018 at 11:10
  • 11
    @Tom A free coffee in a coffee shop itself isn't creepy. What is creepy is that you already knew her order. That is none of your business, and you definitely shouldn't try to point out that you've collected that information. It's one thing when the employees at the coffee shop know your order; they are given that information on a regular basis. It's different when it's a customer; that shows you've been watching her order. Definitely sends out weird vibes.
    – JMac
    Commented Feb 28, 2018 at 13:11
  • 19
    @Tom No sensible person is going to drink a coffee that a random stranger brought to their table. There is no way to know what they might have dropped into it that you didn't see. I do wish fewer of these answers relied on things that work in fiction.
    – user9837
    Commented Feb 28, 2018 at 14:19
  • 9
    @Tom Well I’m in my 50s and also European. Perhaps the difference is that I’m female. Basically I apply the same rules I did in clubs: don’t leave your drink unattended, don’t accept an open drink from a stranger unless you saw the bar staff make it. Though the biggest reason I’d not drink a coffee put on my table like this is because I wouldn’t want to do anything that encouraged such an oddly invasive move.
    – user9837
    Commented Mar 1, 2018 at 7:46
  • 6
    The "courtesy requires ..." part at the end of your answer, to me, sounds not just creepy but manipulative. Just say "hi" at a normal volume, and if she wants to reply she can. Commented Mar 3, 2018 at 0:53

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