Confidence Building
For Men

How to flirt with a woman you like (in a non-awkward, non-creepy way)

November 4, 2017
▪ 4 mins read

Struggling to know how to flirt in a non-creepy, non-awkward way ... Academy Coach JackHQ has some answers

No more spin the bottle

by Academy dating coach Jack

This is a question I started to ask myself when I realised it was no longer appropriate to play spin the bottle as an adult as a substitute for not knowing how to build sexual attraction. As a dating coach at Hayley's Academy, I help guys to learn in a non-sleazy way to flirt and build a sexual connection with women.

Flirting scenario + your frustration

There can often be a thought that when you see a very attractive person, that you think, "I need to woo this lady". You start to think and think some more about the killer lines you’re about to deliver. "When she hears the line about the talking goldfish, she’s going to laugh until her lungs create a vacuum. Maybe she’ll then go out with me and they’ll be a statue made of me."  

She’s talking to her friend, so here it goes. "So, how about that iPhone 8". She then leaves. You're left thinking about what a mess you’ve made of being able to flirt and how annoyed you feel at all sorts of weird stuff you didn’t know you were angry about.  

"I really wish my aunt didn’t chew so bloody loud, someone should tell her!"  

Then you realise that you should actually learn some social skills and gain some perspective on life. Maybe your aunt and that toddler that flipped you off that time wouldn’t annoy you so much anymore. Your frustration is understandable but we have to use that momentum to learn and change for the good. Now that’s out of the way, it's important to say that consciously trying to impress someone is rarely a good strategy.

My thoughts on how to flirt with a woman you like

Gradually working on your social skills until the positive fun aspects become second nature is a great way on how to flirt so she likes you. This is because it is now part of you.  

There are a few key elements and behaviour that will attract and impress people, over and over again.The key is to behave this way constantly, not just around women that you like.It really isn’t likeable or attractive when a guy is only nice or polite to pretty women. It’s incredibly transparent to everyone else to see.

The way in which you behave around people you have no desire for and people that you do, should not differ.  

Whether it’s an elderly neighbour or that really hot girl at your workplace, all of your positive qualities should be on show for that person to see.  

Not just a forced exaggerated version that you can only muster when it suits you. With my dating coach clients in London, it is to incorporate the techniques and behaviours shown on a one to one session and use it in all situations of life. Make a habit of building rapport with people you are not sexually attracted to.

Practice niceness everywhere

Ask the barista how his day is going and make a quip that will make him laugh. It’s very likely going to make anyone else laugh. Including the women, you’re attracted to.

If you can crack the system for making anyone enjoy being around you, you have then cracked the system to attract beautiful women.  

When people feel like you’re giving them special treatment, if they have an ounce of self-esteem it will make them feel uncomfortable and will be aware it isn’t authentic. How you flirt with a woman you like has to come from a place of you being more you than ever before. It should never be a fake performance.

But maybe don't push it with her

With this said, there are of course better ways to flirt and get people generally to be interested in you. The core of flirting strategies is to not flirt constantly. This will feel to her like you're being pushy and you're not really connecting.  

Of course, I want you to flirt with a woman you like by teasing, compliments, backhanded compliments, soft touches, light squeezes but this can't be 100% of the interaction.  

You need to demonstrate standards: that you're not just interested in one thing. The other person will feel the excitement of being unsure of whether they will be pulled in by you or pushed away if they sense you have these standards. Think: if she wasn't a woman I found attractive would I still want to hang out with her?  

Demonstrating that yes you like her but no you're not going to change your whole personality to try and please her is important. There is something creepy about anyone who pretends to be something they're not to try to get a 'result'.

How to flirt

Woman: "yeah, but I don’t like Mexican food"  

Man: "ah it's actually my favourite so I'll have to get you into it...'  

"you're actually quite hard to read..."

"I like how you're ...

treating that dog as if it's you long lost child"  

matching your dress code with your friend, you must be very close."  

really going for the HIIT class... I have some catching up to do..."  

These ways to flirt are very playful: nothing offensive or complicated, it just shows that you are comfortable enough to joke around with this person.

Set a line and do not cross it

It’s important not to flirt for too long as it can actually push the person away. This is because they’ll feel that you are picking on them. You always want to be friendly and be okay to self deprecate if you take it too far. Some people are more sensitive than others so if she doesn't find you funny drop it!  

All good flirting should also show some sincerity which gives her clarity that you like her.  

"you know what I find interesting about you, is ..."  

"you know what’s really nice about you is..."  

Make it then something very specific to that person and it has to be honest.  

Your goal is to connect with her, build her self esteem and demonstrate through how you flirt that you're not dependent on wanting something from her. Instead, you're looking to connect with the women who are right for you.

Hayley Quinn smiling profile
About the author

Hayley Quinn is a leading dating and relationship coach, with 3 million views of her TEDx talk and 18 million YouTube views. She is spokesperson for Match, a columnist for Cosmopolitan, a regular contributor to international media, and has been published by Harper Collins (“The Last First Date”, 2022) and Simon & Schuster (“Do This, Not That: Dating”, 2023).

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