How to be the best man flirt since #MeToo


The movement that was invented to protect women from unwanted sexual advances has put the fear of flirting into many a man.

Will I be misconstrued? Will I cause offence? What are the right and the wrong things to say? How much is too much? What if she accuses me of harassment or even assault?

Suddenly, showing romantic or sexual interested in a woman – or even just being alone with one – comes with the perils and pitfalls of the lost Ark.

However, the rules of this particular game are actually really simple...

If you’ve become wary or just never felt comfortable switching on the charm, here are some tips that might come in useful.

What is flirting?

Flirting is banter with a frisson. It may well be rooted in attraction and be an exploratory mission and enticing precursor to something more, but it’s also about ‘in the moment’ playfulness and feeling fully alive and engaged with life. That’s why someone can be described as a flirt without even trying - it’s just their way of being in the world. 

So much about flirting is in the eyes, whether that’s a sideways glance or lingering eye contact. The mouth too plays its part, in half smiles or full on bobby-dazzler grins, biting your bottom lip or touching your lips with your fingers.

It can be subtle or blatant, gently teasing or outrageously flattering. It can be done across a table or expressed in a soft and appropriate touch on the arm. But most of all, when it works, flirting makes both people involved feel really good about themselves – which is one reason why it makes such an excellent social lubricant.

What flirting isn’t...

#MeToo is movement designed to free women from the, at best, tiresome and draining problem of harassment. It’s got nothing to do with stopping people flirting and everything to do with encouraging respectful boundaries and giving everyone agency over their own bodies and personal space.

Of course you don’t ask permission or obtain consent before flirting, but for that very reason, it’s best not to go out on a limb. Being cautious, sensitive and risk averse is the new black and frankly, it can be just as sexy because when you get clear, full consent, it throws open the door to pleasure.

Unless you know your flirtee to some reliable degree, and have a sense of rapport with them, keep it light and test the water rather than wading in up to your neck. It makes sense doesn’t it? Go in too deep and if the spark doesn’t catch, you’ve got further to go to get back to the safety of shore.

And if you’re approaching a total stranger, be prepared for a No or even to be blanked. She doesn’t owe you anything – you’re a stranger to her too. She may be tired, she may be distracted, she may not be in a flirtatious mood or perhaps she doesn’t fancy you. And while that can feel a bit icky and uncomfortable, it comes with the territory. Just walk away. It’s no one’s fault. Not hers, not yours.

Physical contact can also be dicey. It involves breaking into someone’s personal space and that can easily feel like an invasion and uncomfortable or even threatening.

Obviously context is everything. If she’s touched you on the arm (and you were OK with that), you’re probably pretty safe to touch hers or vice versa, but it’s no guarantee. And just because she touched your arm, it doesn’t mean that touching her shoulder or her hand is an equivalent.

Flirting, like most things in life, requires a healthy degree of good judgement and self-awareness, so it’s helpful to remember the following…

It’s not all about you

Being nervous about flirting is often because you’re focusing too much on yourself: going inwards, fretting and worrying, when your energy and attention need to be going outwards towards the other person. So get interested in what she’s about, what she likes, what lights her up. Put the spotlight on her. 

Authenticity is key

If you’re trying to be something you’re not or acting in a way that feels unnatural, chances are your flirtee will notice.

Your flirting will seem like an act; something fake and therefore not to be trusted. And it’s also likely to feel more precarious and uncomfortable for you too. Your body language will show your unease.

Flirting is not the be all and end all

I can’t stress this enough: you don’t have to be a flirt. It doesn’t make you boring if you’re not. Flirting has been built up as this pinnacle of the mating game and yet, to a considerable extent, it’s a personality trait more than a behaviour. Like public speaking, not everyone is cut out for it or finds it easy stepping out of their comfort zone. Equally, being male doesn’t mean you have to make the first move and a growing number of women are enjoying taking the plunge.

So if you don’t feel happy flirting, don’t be hard on yourself. Step back from that cliff edge and do something that comes more naturally.

Here are five alternatives to getting your flirt out...

  1. Listen and be attentive. If you’re genuinely interested in connecting with this person, let it show. Trust me: the ability to give someone your technology-free undivided attention is a gift. And shy guys can enjoy the luxury of not having to say much. 

  2. Smile. A little warmth in a sometimes chilly world can go a long way. Be the man that makes her feel better about life.

  3. Pay a GENUINE compliment. Don’t feed her a line. Hint: avoid commenting on physical attributes below the neck – stick with noticing her smile – or, even better, think more abstractly. I love your positivity/humour/patience/the way you dealt with that situation etc. 

  4. Flash your GSOH. If you’ve got it, it’s the perfect icebreaker. And one cannot underestimate the power of a genuinely funny guy.

  5. Know that you’re enough. Whether you can flirt or not, having the confidence to be who you are and act and speak from a place of sufficiency rather than needing anything from anyone else will give you a presence that cannot be ignored.

    It’s not about being arrogant or boastful. The point is you really have nothing to prove. Finding that place in yourself is like discovering a super power, but if that feels like alien territory, let’s have a chat. Helping you get to that place is part of what I do. 

Oh and one final thing...

Is it OK to flirt in the office? 

Based on everything I’ve talked about above – what do you think? Because ultimately, you’ve got to make the call.

Flirting can fly or fail depending on the context and there are many variables that make all the difference. For example:

  • Your level of familiarity with each other

  • The mood you’re both in

  • How much you’ve both drunk – or whether one of you has drunk more than the other

  • The amount of mental/emotional/physical energy you both have.

  • Whether either of you have had any negative experiences with the opposite sex

  • If touch comes into it, whether you’ve any kind of physical contact with each other before.

  • Whether you look like her dad/brother/terrible ex…

Ultimately, flirting doesn’t have a formula that will take you from strangers to settled for life with someone. It’s just one way of having a conversation, one way of making contact, one way to show you’re interested in someone.

But it’s not and never will be the only way.

Image: Edward Cisnero