Something that I see a lot of people struggle with when and how it’s appropriate to approach and hit on women. When you’re relatively socially inexperienced, it can feel like tip-toeing through a minefield; if you don’t know what you’re doing, you often run the risk of being creepy by accident. There’s that constant feeling that you’re just one misplaced emoji away from being exiled to the Island of Unfuckable Boys, there to live out your life in monklike celibacy, forever mourning your stillborn love life.

In reality, it’s not quite as complicated or difficult to not be creepy as people make it seem. And as it turns out, the universe conspired to provide us all with another shining example of what not to do.

Last week, former Mugglecast podcaster and Feminspire.com co-founder Ben Schoen attempted to proposition Buzzfeed writer Grace Spelman – first on Twitter,

then he tweeted these at me and they both went unanswered pic.twitter.com/FIL0aPl1SK — Breakfast Bitch (@GraceSpelman) August 17, 2015

then again on Facebook.

Then he moved to Facebook. I politely told him I was seeing someone and then blocked him on FB & Twitter pic.twitter.com/k84dCJ3OrT — Breakfast Bitch (@GraceSpelman) August 17, 2015

When she rejected him, he – to put it mildly – lost his shit.

Here is where he started to get angry. He then tweeted these at me: pic.twitter.com/NJDop6VZ1E — Breakfast Bitch (@GraceSpelman) August 17, 2015

Over the course of the week, Schoen’s behavior has actually provided a handy set of examples of the mistakes many people make when approaching women. So with this recent event in mind, allow me to provide you with an all-purpose guide to the right way to approach women – whether in person or online – without being creepy.

When It’s OK To Approach Women (Or: Consider the Social Context)

One of the complaints I hear all the time from men who struggle with dating is that they feel that any attempt to approach women is automatically creepy. They hear the various horror stories about guys being labeled as creepy for trying to hit on women at cons or approaching women they see on the bus or on the train or trying to slide into their DMs and then lament that there are no acceptable ways for men to hit on women any more. Almost every time a woman shares a story about just trying to get through their commute or catch up on their reading during their lunch hour, there’s a host of men complaining about how this isn’t fair to their dicks.

Ignoring the fact that most people don’t meet their significant others through cold approaching randos on the bus or train, the key to knowing when it’s ok to approach women is to consider the social context of the situation. At any given time, there are generally accepted rules that define what behavior is considered acceptable and appropriate for the situation. The social context of being at church, for example, demands radically different behavior than being at a nightclub.

When your behavior goes against the accepted social context, then you end up making people uncomfortable. You’re incongruent with the location and that can be incredibly creepy to people; it tells others that you either don’t understand the rules that govern what is and isn’t acceptable or you don’t care. Someone who doesn’t care that it’s not appropriate to yank a book out of somebody’s hands or pull the earbuds out of her ears is sending the signal that they may well not worry about little things like “consent” either.

By that same token, there are times and places where the social context says that says that it’s acceptable to approach a stranger and that a person’s presence is a general acceptance of the social contract. These places include:

Most bars and clubs

Parties

Classes

Work

Meet-ups

Online dating sites (This does not include Facebook or Twitter.)

This is, obviously, not an exhaustive list and there are variables that can affect what behavior is and isn’t appropriate; the same behavior that’s appropriate at a club is creepy as hell at work. But learning to navigate the subtleties of these rules is part of developing your social calibration.

And speaking of which:

Consider Your Skill Level

Whenever we talk about times when it’s not appropriate to approach or hit on women, people will inevitably bring up someone they know – either personally or friend-of-a-friend – who broke “the rules” successfully. The fact that “they” did it (for suitably vague definitions of “they”), then clearly it should be open to everyone, no?

Er… no. That’s not how things work.

As I’m always saying, being good with women is a skill and some people are going to be more skilled than others. The fact that Michael Jordan can pull off an astounding dunk doesn’t mean that anyone who plays basketball can; similarly, the fact that somebody was able to pick up a woman while on the bus or walking down the street doesn’t mean that everyone should give it a shot. The more socially calibrated and experienced you are, the more you can pull off; people who’re more socially calibrated are better at reading the social context, picking up on the other person’s signs and knowing how – if necessary – to extract themselves if things go badly. Someone who is socially well-calibrated can get away with more than someone less calibrated because they have a better sense of where the line is and how close they can get without going over.

The less experienced you are, the less advisable it is to try to take on riskier approaches; the odds are against you and you can end up making yourself seem creepy when you don’t intend to. A 5th level paladin isn’t going to survive going through the Tomb of Horrors and somebody who doesn’t have much social experience is better off sticking to accepted social spaces to approach women. This is one of the areas where Schoen seriously falls down. Pushing and pushing for Spelman to respond to him, switching social media platforms when she wouldn’t respond to him on the previous one? This is someone who’s demonstrating poor social calibration; he’s getting a very obvious brush-off and keeps trying anyway. The almost obsequious fawning in the message on Facebook makes it even more clear that this isn’t going to go anywhere good; sucking up isn’t a good look on anyone.

So how do you gauge what’s likely out of your level? It’s going to be an inexact process at best; it’s not as though grinding in bars gives you 120 XP per hour that culminates with your hitting the cap as a level 80 Pick-Up Artist.

As a general rule, the more successes you have – getting working phone numbers, first dates, second dates – the more risks you can reasonably take. If you’re still struggling to get that first date, then you’re better choosing lower-risk, lower-investment approaches like meeting people through your social circle. Just remember: being well-calibrated and socially successful doesn’t mean that you’re guaranteed success; everybody has off days and some people will just not like you no matter what.

While there are obviously no hard and fast classifications, this list should serve as a decent rule of thumb.

Dating 101 – Online dating, warm approaches, meeting friends of friends, parties

Dating 201 – Cold approaches at bars and clubs, some low-key, low-investment daytime approaches (bookstores, coffee shops, comic stores, etc.)

Dating 301 – More advanced daytime approaches (the mall, the gym, grocery stores)

Dating 401 – Street approaches, public transit, etc.

Notice how Facebook and Twitter aren’t on there? There’s a reason for that: it’s a fucking stupid idea.

Don’t Assume A Level Of Intimacy You Don’t Have

One of the hard and fast rules of dating and not being creepy is recognizing that everybody has boundaries and those boundaries are flexible; some people have greater levels of access to us than others because we have different levels of intimacy with them. One of the keys of what makes somebody creepy is very simple: creepers assume a greater level of intimacy than actually exists. A close friend might get away with an impromptu hug or a playful ass-grab; an acquaintance or total stranger who tries to pull the same move would get a surprise visit from the Slap Fairy.

People who assume (or try to take) a greater level of intimacy than they actually have are creepy because they’re ignoring your boundaries.

In the case of Ben Schoen’s attempt at wooing of Grace Spelman, he assumed a far greater level of intimacy than actually existed; the only contact they had was that she friended him on Facebook when she was fourteen. For nine years, they had no contact; they never interacted on Facebook or Twitter until he tweeted at her out of the blue. The first message was relatively innocuous, but the ones that followed became weren’t – he was making the kind of jokes-but-not-really that assume a greater level of familiarity between the two than actually existed. Two people who had at least a passing relationship online might get away with tweets like “For my birthday, I want @gracespelman to follow me back”; from a complete stranger, that’s just unsettlingly creepy.

Approaching people you don’t know and have no connection to means that you have to behave accordingly. Tracking them down on social media, randomly texting them (when they didn’t give you their number) or proclaiming your undying devotion for them when you don’t actually know each other are all examples of assuming excess levels of intimacy. So does trying to escalate things physically (demanding a hug, trying to put your arm around someone you’ve just met, etc.) or turning the topic to sex when it’s not wanted or warranted.

Respecting somebody’s boundaries, on the other hand, is a mark of respect as well as social calibration. It shows you that you value their comfort and respect their social, emotional and physical safety. The guy who shows respect (and let’s be clear: there’s a difference between respect and being a suck-up) is someone who’s going to have far greater success with women. Why? Because women will feel comfortable and secure around them. Not sure if something’s off limits? Ask. It may be a little awkward, but a touch of awkwardness is easy to recover from; creeping somebody out, on the other hand, dries out panties faster than a tumble dryer set to “high”.

One of the things you need to keep in mind: people are able to set their boundaries wherever and whenever they like. It’s not simply a matter of being attractive or unattractive; the hot guy can be creepy as hell while the gaunt, bug-eyed chain-smoker gets ass like a drunk at a livestock auction with a stolen credit card. But even if they do decide that the hotter guy gets permission for greater intimacy, that’s their decision. Insisting that it’s not fair or that you “deserve” equal access is entitled and creepy as hell. In fact, while we’re on the subject…

You Aren’t Entitled To Anything

If you want to make sure you don’t cross the line from “cool” to “creepy,” you need to recognize that women don’t owe you anything. This includes an explanation as to why they rejected you or even a response. This is doubly true if you don’t have any sort of actual social connection to this person. If you’re a complete stranger coming up to them in a bar or messaging them on OKCupid, they have absolutely no obligation to so much as acknowledge that they received your email. Is this rude? Yeah, it can be. But politeness isn’t the same thing as obligation, and insisting that people owe you a smile, a reply or a date implies that you somehow have authority over them and that your wants cancel out their autonomy.

Once again, this is boundary-pushing behavior; by insisting that you are somehow “owed” something, you are saying that the other person does not have the right to decide their own actions or responses. If you already are demanding things of strangers – even something as relatively innocuous as a smile or a “hi” back – you’re establishing a precedent where you expect more of your desires to be reciprocated, regardless of whether the other person is interested or not.

To give an example, after Spelman had blocked him on Facebook and Twitter, Schoen emailed her directly:

Then last night he sent me this email: pic.twitter.com/2wM0t0P3tl — Breakfast Bitch (@GraceSpelman) August 17, 2015



Everything about that email reeks of entitlement and a belief that Spelman is somehow required to justify her actions to him. The pseudo noblesse oblige of “I could have put you in your place with my stinging retort but I chose not to,” only heightens the disconnect reality that makes Schoen’s behavior creepy. It even carries an implied, if somewhat impotent threat that he oh-so-generously decided not to follow through on… but he totally could have.

Another factor to keep in mind is that meeting basic standards like “not being a rapist” or being a “good guy” doesn’t entitle you to a woman’s time or attention. Similarly, your various accomplishments, however impressive they might be, don’t create an obligation for someone to bow to your whims. You want somebody to give you the time of day when you approach them? Be someone worth talking to. Be interesting. Be charming. Be respectful. Demanding a response just because you’ve paid what you think was a compliment isn’t respectful, it’s being a douchebag and it’s creepy. It demonstrates that you weren’t interested in just paying a compliment, you were really making demands on her time and attention. That sort of behavior is a distinct turnoff and makes sex disappear like dust in the wind.

Accept Rejection With Grace

Hard truth time: you’re going to get rejected. Everybody does, no matter how hot or how skilled they may be. You could be rejected for a multitude of reasons which could range from your saying something wrong to the moon being in the wrong house for her to date right now. At the end of the day, the reason for your being rejected doesn’t matter; it just means that for whatever reason, the two of you were not going to work out. It’s on you to accept that rejection with grace and aplomb.

Why? Because people who’re able to handle rejection well ultimately get rejected less. Being able to take rejection and not letting it either destroy you or turn you into a red-pill-fueled rage monster is a mark of emotional intelligence and higher levels of emotional intelligence correspond directly with greater dating success. Someone who realizes that one rejection isn’t the end of the world? That’s somebody with confidence and self-assurance. He may be single now, but he won’t be single for very long.

Accepting rejection with grace means, among other things, recognizing and accepting soft “no’s” – those attempts to soften the blow of the rejection by couching them in terms that make it seem like it’s less their choice and more just an unfortunate inevitability that’s nobody’s fault. When someone says that they’re not interested in dating right now or other attempts at deflection, they don’t mean “try again later”; they expect you to mentally append a silent “you” in that sentence. Don’t worry about missing your window; if someone is genuinely interested in dating you and it really is circumstance getting in the way, they will make sure you know.

Similarly, no response – such as when your online dating emails go unanswered – is a response. It’s just not the response you wanted.

The best thing you can do if you get rejected is to simply move on. If they tell you no, then say “Ok, thanks. Best of luck to you!” and look for someone who digs what you have to offer. If you get no reply at all… shrug your shoulders and move on; there’s no profit in trying to provoke a response and pushing more will turn that “no” into a “FUCK OFF”.

The worst thing you can do? Make a fuss. Get pissy with the person who rejected you. Demand answers, explanations or just straight up start insulting them. Now I get it. You’re hurt. Your ego’s stung and you’re going into defensive mode to try to get yours back. Trust me: nobody’s going to be impressed by your turning around and calling the other person fat, ugly, slutty or a bitch, especially when you were begging for their number earlier. At best, you’re justifying their reasons for rejecting you in the first place. At worst… well, you realize screenshots exist, right?

Nobody ever looks good having a post-rejection freak out at somebody. Just witness Shoen’s “BURN IT ALL AND PISS IN THE ASHES” response on Twitter for the last two weeks. The standard “HA HA, YOUR HATE ONLY MAKES ME STRONGER” posturing is part and parcel of the “you can’t reject me, I’m rejecting YOU and also you’re fat and smell funny” gambit, where you pretend that you’re above it all as you flame out, only to rise from the ashes like a fedora-bedecked phoenix with a mighty cry of “M’lady!”

You don’t want to be that guy. It’s uber-creepy. It’s a sign that you’re just not ready to date anyone.

But the guy who has the confidence to let rejection slide, to feel the sting but not let it destroy him? Who can take a rejection with grace? He’s the one who’s going to succeed in the long run. You may not get that particular woman… but other women will notice these things. They pay attention. And a guy who can avoid being creepy, who can show respect? Someone who’s fun and socially well-calibrated? That’s the kind of man women like.