Anyone who reads my site for long enough knows I’m a big proponent of the cold approach. Learning how to approach women, strike up a conversation and charming them into being interested in going on a date with you is a difficult – but important – skill to master. But just as important as it is to be willing to approach women you don’t know, it’s important to know when you shouldn’t be approaching them. As nerve-wracking as it might be for you to approach women, it can be an even more tense situation for the women being approached. Almost every woman out there has a story about being harassed by guys who wanted to “just say hello” and who thought that their desire to introduce themselves overrode her right to be left alone. Who goes from being a stranger to a full-blown creeper in the span of a couple sentences because they won’t take a hint.

Of course, there will always be the wags who will say “clearly, the answer is to just never approach women ever” while others will demand to know how they’re supposed to meet women if they don’t approach them. They will complain that it’s unfair to miss out on missing someone awesome just because some creeper somewhere might have weirded a woman out. This is one of the reasons why social calibration is one of the most important parts of getting better at dating; recognizing the times when it is and isn’t appropriate to approach women is vital – not just to your dating success but to avoiding being creepy by accident. One of the keys to social calibration is understanding the cues and context that tell you when a woman is open to being approached and when she isn’t. Now an obvious caveat: people are people and everyone sets their boundaries where they see fit. There will always be exceptions to every rule and people who may be receptive to being approached under these circumstances. Many people – myself included – have experiences where they have successfully gotten a number or a date or what-have-you from a bartender, a waitress, someone they met on the bus or the train. HOWEVER. You can’t bank on people being one of those exceptions. So unless she is giving you very explicit indications that she’s interested in talking to you… give her a pass. It’s better to “miss out” on an opportunity than to end up being yet another warm body in the asshole conga-line of her day.

So let’s look at 5 times when you shouldn’t try to approach women.

When She’s Giving the Don’t Bother Me Sign

One of the keys to getting better at interacting with women is to understand the differences in how men and women are taught to communicate. Women are taught to be indirect when communicating their desires and interests – especially when it comes to interacting with men – and are more likely to rely on non-verbal communication. A woman who’s interested in being approached, for example, might signal the guy she’s attracted to with the classic “lock eyes, look away, look back” move. But just as women tend to signal their interest with what’re known as “approach invitations”, they’ll also signal that they really want to be left alone the same way.

For example: one of the most obvious non-verbal signs that a woman wants to be left alone is that she’ll refuse to make eye-contact. Locking eyes is one of the classic approach invitations, so she’ll go out of her way to not meet anyone’s eyes. Staring straight ahead, looking down, staring resolutely at her phone, giving the thousand yard stare or resolutely looking anywhere but at a person are all signs that she’s trying to avoid giving someone the idea that she wants to talk to anyone. Similarly, she may use obstacles – especially clothes or accessories like a hoodies or sunglasses – as a physical barriers to eye-contact.

Wearing headphones or earbuds are another universal “do not disturb” sign; in fact, many people will wear earbuds without actually listening to music specifically so people will leave them alone. It’s another way of putting a physical barrier between themselves and someone trying to get their attention.

Pro Tip: pulling out her earbuds , waving your hand in her face or otherwise trying to force her attention is going to ensure she thinks you’re an asshole, no matter how much you really want to know what she’s listening to.

Other “do not disturb” signs include when she’s reading, writing or working on her laptop. If she’s in a public place – a cafe, a Starbucks, what-have-you – and she’s reading or on her laptop, then the odds are that she’s there because she really needed to get out of the apartment for a while. This means she’s there to work or study, not to flirt. And no, it doesn’t matter if you notice she’s updating her Facebook page instead of working on her thesis; if she was interested in talking to somebody, she wouldn’t be focusing on a computer screen. If you really want to ask her for her opinion on the Jim Butcher book she’s reading, the you can wait until she’s put the book down, rather than plopping yourself in in the seat next to her and demanding that she pay attention to you.

On Public Transportation

One of the worst possible places to approach women is on just about any form of public transit. You’re already dealing with people who are frustrated, stressed, hungover or generally wishing they were anywhere else. All anyone on the Muni, the eL, the Yamanote line, the Underground, or any other form of mass transit wants to do is get through their commute with as minimal irritation as possible. The last thing they want to do is actually interact with the teeming masses of humanity around them.

This goes double for women. In fact, for many women, mass transit is less of a convenient and economical way of getting from place to place and more of a gauntlet of horror, frustration and harassment that they must run on a daily basis… and that’s on a good day. Almost every woman who’s ever had to take the bus or the subway or the train has had an experience of being harassed – ranging from guys who see nothing wrong with demanding a response from women who clearly want to be left alone to the incredibly dangerous. This is the background radiation of her daily commute – never knowing if the guy who sits next to her or around her is going to just be annoying or if he’s going to jerk off in front of her.

And to make it worse: she’s effectively trapped with the guys who are harassing her. Her options are to get off before her stop or hope that he gives up and goes away. Getting off early is no guarantee that she’s going to get away from the guy – there’s really nothing stopping him from deciding “no, this is my stop too” – and adds other risks like being late to work and losing her job. And if he’s someone who regularly takes the same line she does… well, now she can expect to see him every goddamn day.

Trying to approach women on mass transit – even that cutie you see every day on your morning commute – means that you’re trying to approach somebody who is already suffering from profound creeper fatigue. Yeah, you may not be a creeper, but she has no way of knowing this. She just wants to get through the day without dealing with another guy who thinks that a woman taking mass transit has signed up for the Transit Authority Speed Dating Service . Public transportation is not a safe space for women and she will already have her guard up when you try to say hello. If she wants to talk to you, she’ll let you know. Let her make the first move; the last thing you want to do is cause the woman of your dreams to associate you with other mass transit creepers.

Also: remember what I said about the “do not disturb” signs? This goes double for when they’re on the bus, the subway or the train. A woman reading or listening to her headphones is making a determined effort to shut the world out until it’s time for her to get off at her stop.

At Work

Approaching women while they’re at work is a rigged game, especially if they’re working in the service industry or any job where a woman has to be “nice” for a living. Don’t get me wrong; to some guys, the cute barista is more appealing than any other woman on Earth… but trying when it comes to the age-old question of “Does she really like me?” the answer is usually “just as a customer.”

Take anyone who works for tips – waitresses – especially ones at restaurants like Hooters or Twin Peaks , bartenders, shot girls, go-go dancers etc. Their job description is almost literally “Flirting For Dollars”. This doesn’t mean that these women are cockteases or are being dishonest, but a certain level of flirtiness often means a heavier tip from male customers. It’s professional flirting without intent. But even those who aren’t overtly flirty have a vested interest in getting you to like them – it’s part of what helps bring customers back. Unfortunately, there are plenty of people who mistake professional niceness for genuine interest and assume that the waitress or the bartender is really into them. Those cute designs in your latte foam are more about getting you to be a regular than sending you secret affogato-encoded love notes.

But beyond not mistaking niceness for interest, there’s one major complicating factor: they are at work. There’re not there to get dates or make new friends, they’re there to do their job. They literally don’t have time for prolonged flirt sessions and, frankly, most of them would like to get through their workday with minimal hassle.

“But I could be the customer who makes her day better by flirting with her!” I hear you cry. You know who else thinks this?

Almost every other guy who she meets.

Seriously; women in the service industry deal with guys who think that they are the Casanova she’s been dreaming of all these years. And let me tell you: the barista you have a crush on has been dealing with it all goddamn day. When you’re the latest in a long line of people who want to chat her up over her love of Baudelaire and her Pinterest-inspired tattoos, even the most charming motherfucker is going to have to push through some serious creep fatigue.

Once again: it is known to happen. But the best way to flirt with someone in the service industry is to be a regular and cultivate a relationship over time. If you’re a regular, you’ll have more opportunities to get to know one another over time. But even so: it’s one more arena where it’s better to let her take the initiative.

At Night (Except In Social Spaces)

General rule of thumb: don’t approach women at night.

The social contract changes when the sun goes down. What is tolerable – if not expected – during the day is potentially threatening at night. Asking a woman for the time or directions or bumming a light during the day is completely normal. The exact same behaviors at night seem like the prelude to a mugging. You may have nothing but the most noble of intentions, but trying to approach women walking along the streets at night is most likely going to make them nope right the fuck out of there on the express train to FuckThisShitville.

Even relatively busy or well-lit thoroughfares are no-go’s when the sun’s gone down. Yeah, the Champs-Élysées may be incredibly gorgeous at night when the lights are lit, but it’s still not the time to try to approach strangers.

The obvious exception are in social spaces – that is, places where socialization is not only expected but encouraged. Street fairs, block parties, outdoor events… these are times when yes, you can reasonably approach women and not come off as “Hi, my name is Chad and I’ll be your mugger this evening.” Worth noting: the later it gets in the evening, the sketchier you appear trying to meet people at night. Down on 6th St. in Austin, the streets are crowded well past 1 AM… but once the bars close, if you’re approaching women you seem less like the cool guy and more like the hyena at the watering hole looking for the gazelle who got left behind by her drunk-ass friends.

You wouldn’t think this would need to be said… but just as every woman’s dealt with harassment on mass transit, they’ve also known the guy hanging around the outside of the bar or the bodega or the bus stop who wanted to know what her name was or to tell her to smile. Don’t do it.

Never Approach Women On Planes

The last time I flew Virgin America, we were treated to a special message from Richard Branson touting the latest service available to VA passengers – the ability to order a drink for a stranger on the plane. It is, we are assured, a great way to get to know somebody. And who knows… maybe you might end up making some special plans before you get to the baggage claim. This is the sort of bad idea that can only be responded to in gif format…

Airplanes are quite possibly the single worst place you can try to approach women – even with billionaire enabled cocktail service. Everything that makes approaching a woman on mass transit a bad idea is amplified by a factor of EVERYTHING when you’re on a plane. On the subway, she has the option of moving to another car. On the bus, she can getting off at an earlier and try to catch a taxi instead.

On a plane, however, the person is stuck with you for the next two to four hours – or more – with absolutely no way of getting away… and this can be frustrating at best and outright skin-crawlingly awful at worst.

Look at it this way: you’re already stuck in a metal tube flying through the sky in defiance of the laws of God and man. All you want to do is get through the flight with as minimal irritation as possible and some dude is trying to chat you up, edging themselves into your personal space, peppering you with inane questions and getting their halitosis all over you. How receptive are you going to be to being hit on by your neighbor for the next several hours?

But then it gets worse. First comes the probing: where are you staying, how long will you be there? The revelation that he’s single or that he has an arrangement. The barely-concealed sexual inuendo. The “just kidding, but not really” jokes. The hand on the knee…

To make matters worse? Not only are you stuck with them for the flight but if you’re both headed to your final destination, they’re with you all the way to baggage claim.

Now imagine this happens to you regularly when you fly.

Don’t hit on women on planes. Ever.

TL;DR – Show Some Consideration and Respect

Look, I’ll be the first to advocate approaching women you don’t know, expressing interest, flirting with them, trying to get a number, the whole nine yards. I know that sometimes you’ll see the (latest) woman of your dreams and you’ll feel that pressure that says “if you don’t talk to her nownownow you’ll miss your opportunity and never see her again”. I totally get that. But as much as you’re looking to make the most of this once-in-a-lifetime opportunity, you’re still going to blow it when you’re rolling up on her at a time when she is not open to meeting somebody. There are times when all a woman wants is to not have to deal with anyone, whether it’s you or Ryan Gosling and Tom Hiddleston at the same time. Being respectful of her space and showing her courtesy is much more likely to make a positive impression on her than being one more headache in her daily commute.

There’s a time and place for everything. And these are not the time, nor the place.