The Difference Between Flirting and Harassment


The line between flirting and harassment is unclear for many. Men are now scared to attempt anything with a woman, and women are conditioned to believe that all men are dangerous. This is killing the dating scene. However, flirting can be safely done if the man’s intentions are giving, he gives respect to the woman’s reaction, and he acknowledges the context. And it’s important that the woman knows the difference between being harassed and just feeling a bit awkward.


In a nutshell, many men don’t know how to flirt (introduce sexuality into an interaction), and many women don’t know the difference between well-intentioned but poorly delivered flirting, and actual harassment.

Dating is becoming difficult, and fraught with peril. Men are worried about being perceived as abusers, women are worried about being abused.

The gap between the sexes is widening.


We in the Western world are becoming a fragile generation.

With all the big wars and major survival issues behind us, we are turning on each other. One of the worst manifestations of this is how men and women are becoming divided.

The climate of hostility between the sexes (created and perpetuated by mainstream media) has us all confused and scared. We’re told that there is a BIG problem with toxic masculinity (a supposedly inherent aggression in males).

You start to get an impression that all men are a risk to women. This is bullshit, but unfortunately we are led to believe that being a sexual man is inherently dangerous.


Because of this, some men are afraid to interact with women sexually, even though this is required for relationships to form. This leads to half-hearted, indirect and inappropriate attempts at flirting. Such hesitancy is interpreted as creepiness.

Other men aren’t afraid, but are socially awkward or completely lacking in self-awareness, because there’s no room for learning or honest feedback. Their attempts come across as creepy and weird, yet they receive no corrections or support.

Women are afraid of men’s intentions. Pre-1960, you could at least be relatively sure that a guy would only hit on you if he was looking for marriage. Casual-sex was rare. Nowadays, a woman can’t be blamed for feeling that all men are just trying to get some and don’t give a fuck about you as a person.

Good men don’t want to be mistaken for rapists, so their sexuality is becoming infected with fear, which comes across as either asexually platonic, or creepy and awkward.

Women don’t want to put themselves at risk, so they react brutally to almost any man’s attempt to flirt or interact in a sexual way, especially if the guy is nervous. This perpetuates the myth that male sexuality is inherently dangerous, and discourages the good men from trying to learn.

We’re caught in a loop.

The longer this continues, the more sexually passive and afraid men will become, until it will be almost impossible to create a genuine sexual relationship. Is this what we want?


A man’s behaviour is mostly neutral. Once we get past the extremes, like sexual assault and rape, we get into a grey area where the context and perception of the behaviour defines it.

For example, if a bold, confident, and caring man gives his date a smack on the ass, she’ll probably love it. But if a socially awkward and hesitant guy randomly strokes his work colleague’s arm, she’ll probably freak out.

The first guy is different from the second guy, and the context is different. Guys are expected to know how to navigate these differences, but how is man to know what’s right and wrong if he’s never been taught?

It’s like trying to adjust to a new culture without a guide. It’s all guesswork. But at least with a new culture, you can safely make mistakes – the locals will just laugh and correct you.

In the case of flirting, however, it’s terrifying to make a mistake and there’s no support, so the average guy can’t even engage in trial-and-error experimentation.


First, we must accept the facts: too many men simply don’t know what it means to act right in these situations, and too many women are overreacting to non-abusive sexuality, labelling everything as “harassment.”

Yes, harassment and assaults do frequently happen, but these are not the same as a guy just being masculine or expressing his sexual desires.

Transitioning from platonic friendliness into sexually-charged flirting and escalation is the bit guys are getting stuck on. So I’m going to assume that guys reading this are like I once was – completely clueless – and spell it out clearly.

There are 3 factors that make the difference: intentions, respect, and context.


WHY you’re doing this is more important than what you’re doing or how you’re doing it.

If you’re doing it to GET something – e.g. love, sex, approval, attention – then you are more likely to come across as harassing.

Instead of trying to get, try to GIVE.

Watch this video for more:

Before you start expressing attraction, get your intentions sorted. Aim to achieve these purposes.

Intentions that define flirting:

  • Giving your attraction and personality to others.
  • Playfulness.
  • Connection.
  • Having fun.
  • OK with not getting anything in return.

And catch yourself when you’re slipping into these more unhealthy intentions.

Intentions that define harassment:

  • Convincing her to have sex with you.
  • Trying to get validation from her.
  • Expecting her to reciprocate.
  • Expecting a reward for initiating.
  • Degrading, hating or humiliating women (even Nice Guys are known to do this after a rejection).


Respect is about allowing someone to have safety and space to react. They must feel that it’s OK to show their true feelings in reaction to your attempted flirtation.

Acknowledge any likely pressure or danger. Give them the freedom to safely reject your advances.

Give space with your body. Allow them a path to leave (don’t physically block or corner them). Keep your upper body tilted back to create the feeling of breathing-room – at least until things get more intimate.

Speak slowly, with plenty of pauses. When you’ve finished sharing your attraction with them, remain silent to allow them a chance to respond. Let them finish their response and never fight against it. Never try to convince them to respond positively.

If it goes weird, just call it out. Say “Wow, that made things awkward, man I am really terrible at this whole flirting thing today, right?”

If they are not keen, or otherwise uncomfortable, acknowledge this and back off. Thank them for interacting with you, and always wish them a good day. If you’re uncertain about their reaction, then reassure them that you’re not going to put any pressure on them to continue.

For more on this, check out my post on how to tell someone that you like them:

Harassing and disrespect is:

  • Coercion – trying to dominate someone toward a positive response.
  • Intimidation – invading their space or privacy.
  • Pressure – socially risky context (e.g. in front of an audience), begging and pleading, subtle threats, sulking.
  • Indirect – hiding your true intentions and feelings, using text instead of speaking in-person, masking anger or attraction beneath humour, sideways language, or judgmental compliments (‘negs’).


The less experienced and confident you are, the more context matters.

A naturally confident, charismatic guy will get away with flirting anywhere, because his inner-self is solid and there is no shame. His frame will dominate – others will feel OK with whatever he believes is OK. Even if he’s obnoxious he’ll be forgiven – “That’s just Dan, he’ll say anything!”

If this isn’t you yet, then you need to be more careful about context. The more anti-social or professional a setting is, the higher risk flirting becomes for guys with lower confidence or social intuition.

Start with highly social situations, like bars, parties, BBQs and friendly gatherings. This is where you can practice getting your intentions and respect right.

Once you’re more comfortable with flirting and attraction, you can allow yourself to be more playful in riskier settings, like work, the gym, and coffee shops. Always get feedback to calibrate your social intuition.

When in doubt about the context, simply prefix your flirty statement with something like, “I know this is probably wrong to say in this environment…” to show you’re aware of how they might feel.


Knowing the difference between flirting and harassment is as important for women as it is for men. If you’re not clear on the difference, he can’t be either.

You’ll be pressured to think all men are rapists. This isn’t true. You won’t know who’s dangerous unless you can figure out who isn’t dangerous, because the real predators hide among the shy and awkward (e.g. you’d be amazed at how predatory male-feminists can be).

Giving a guy the benefit of the doubt is not the same as naivety – you can let the guy make a first attempt without pulling out the rape whistle. Awkward, nervous and shy are not the same things as creepy, rapey and evil.

Men are less intuitive than women and cannot read minds like you can. We need a clear rejection if we’re off-base. Make your discomfort clearly known, not just implied, but do it gently. You’ll know he’s just socially inept when he respects your rejection.

If he’s open to it, give him guidance and feedback – odds are no one else will. The best rejection I received was a girl saying “I’m not interested but I’m flattered and I admire your bravery for doing this.” This girl had a massive positive impact on my fear of women and my loneliness resentment.

If he reacts with aggression, pressure or persistence after you’ve given him a clear “No,” then you can be sure it’s getting into harassment territory. React accordingly – make a scene, get support from a friend, press charges or lay a complaint.


Guys, keep this checklist in mind every time you want to express attraction, initiate a potential romance, or otherwise flirt:

  1. Give her your attraction as a way to practice being honest, playful, and to develop your own courage. Don’t expect anything in return – she doesn’t owe you anything, ever. No woman does.
  2. Pay close attention to her reaction and adjust accordingly to any signs of discomfort.
  3. Make it safe and easy for her to comfortably reject you – give her space to react without fear.
  4. Give it to her bold, simple, straight and honest, so there could be no misunderstanding.
  5. Smile and maintain eye contact, and wish her well even if she does reject you. Be grateful she gave up her time for you.

If you need more help with this, drop me an email

4 Responses

  1. My women friends berate me for not approaching / escalating with women who they say obviously like me. I’m a 43 year old man and I’ve never asked a woman out – even if I’m really attracted to her – because no sign or pattern of signs is – or could be – sufficient for me to feel comfortable trying to escalate to the sexual level. Of course I’ve never experienced any form of intimacy either. And I will not “touch her arm” or any of that (which people advise is required to move forward) because unless a woman specifically consents in advance to my touching her, doing so would be offensive and therefore I’d be opening myself to an accusation. So many sites tell guys to focus on the present and not the outcome of interacting with women. I don’t see how this is possible when I have to be extremely cautious in order to avoid creeping a woman out by my presence and thus opening myself to trouble.

    1. Hey mate, I can see you’re paralyzed by the fear of rejection – manifested in your imagination as “creeping them out”. Tragically, your “extreme caution” is probably far more creepy than touching an arm or trying to escalate with honesty would be (e.g. expressing attraction verbally).
      I feel for you mate, many of my clients are lifetime virgins who are trapped in a platonic hell because they don’t know how to get started without feeling terrified. It will take some serious psychological reprogramming to fix this issue for you, but it IS fixable. You can get to a point where you feel comfortable and safe expressing attraction and escalating things sexually, without any real risk of causing offence or creepiness.
      Email me if you’re ready to do that work

      1. Hi Dan – no, I’m not paralyzed by fear at all. I’m a fundamentally unattractive man who realizes that since in order for flirting to be acceptable, it needs to be reciprocal. Since no woman could be sexually attracted to me, no matter how much effort I put into getting to know her socially, flirting would be offensive by default. As such, escalating to anything non-platonic, including light touch, etc. is out of the question. I say I’m fundamentally unattractive because having observed other guys escalating with women, it is clear that whatever they have that makes them attractive to women, I do not have – and do not have the ability to obtain.

        1. Attraction is more about behaviour and confidence than anything else, both of which can be learned. So any man can be attractive. I’ve coached guys who have been rejected every single time they’ve ever shown interest in a woman, and within 6 months to a year they’ve successfully created a loving relationship. It was their beliefs that needed to change. I’ve never met a guy who cannot possibly attract a woman unless they stubbornly refuse to challenge their beliefs. Even the most good-looking and rich guys can continuously fail with women if they have incorrect and limiting beliefs.
          I know you feel resistance, and probably part of you clings to the identity of “unattractive guy” because it’s safer than taking risks and getting rejected. But without even knowing you at all, I am 100% certain that if you had the same beliefs as those guys you observe you’d get similar results

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