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Four BIG Flirting Mistakes That Are Holding You Back With Men…

Stephen Hussey

It sounds so simple: “Just go over and flirt with him”.

You’ve seen the movies.

An elegant sip of a cocktail. Sassy hand on hip. Hair falling seductively over one half of your face.

“Sooo…” you say, legs crossed over a bar stool, your eyes meeting his, “What brings you here?”

In your head it’s all one smooth, ridiculous cliché.

But then he walks over and it’s time to actually do it. What do you say? How do you “be flirty”?

You try your best, but you just end up asking question after question, getting into all the usual boring talk: work, work, siblings, family, work, where do you live, work, etc. etc.

Suddenly, the problem is obvious: “I’m stuck…I’m stuck in my run-of-the mill, everyday, normal, boring personality.” (Your words, not mine. I don’t think you’re boring at all. I think you’re lovely.) :)

There are many roles we play in life. But if we get too locked into one of these roles, they can hold us back in dating.

In fact, there are four personality types that you may be stuck in right now. Having some of these characteristics isn’t a problem by itself, but if you only play one of these roles, it will kill your attraction with guys. Being too much of one thing is one of the biggest flirting mistakes you can make.

So take a look below and see if you fall too far into any one of these types:

Personality Type 1 – The “Super-Ambitious-Always-Busy” woman

You work. Really hard. Every day. So much so, that you constantly describe yourself as a “busy” person. Talking about your job, and how much you love it, dominates every first conversation.

The problem is: who cares?

Is it good to be passionate about your career? Absolutely. Is it good to be borderline-obsessive to the point where you’re always playing a competitive game of “who’s life is more important?” with every guy you meet? Not unless you want to be the dating equivalent of kryptonite.

Guys love passionate women. Passionate and work ethic is powerful. Being compulsive and driven to the point of crowding out everything else isn’t. If you spend too long in “ambitious-hard-nosed-worker” mode, you can never really create that fun, playful mood that makes someone drawn to you on a physical level.

Personality Type 2 – The “Jokey-buddy” woman

Making wisecracks. Excessive sarcasm. Lots of “playful” punching on the arm and constant attempts to make jokes at his expense.

Funny is good. Being only funny is not. It’s exhausting and attraction-killing. Flirting is all about being able to settle into a different mood. Yes, there are jokes, but there’s also silence, prolonged eye contact, a sly smile, slow touches, genuine compliments, and all the other things that fire off the tiny explosions in his brain that make him think, “holy shit. How do I get her number??”

If you live in joker mode, you’ll leave him scratching his head as to whether he should be taking you on a date or inviting you to fire nerf guns in the park (which actually doesn’t sound like the worst idea as I write it, but you get the point).

Personality Type 3 – The “Mother” woman

There’s no problem with being a mum and owning that part of you. I’m firmly in the camp that you shouldn’t apologetically approach the topic of your kids, as though you had Darth Vader living in your house.

But it’s very easy to get locked into the identity of only “being a mother”. Someone who does school runs, makes lunches, puts kids to bed etc. etc.

Although it’s true that being a mother is likely to be a huge part of your life, you’re also probably many other things: a traveller, a deep-thinker, a creative, a dancer, a passionate lover, a movie-nerd, a friend, a fun sister – you have many sides – so it’s important not to let the fact that you have kids become the only part of your character if you want to get long-term attraction.

You’re a mother and have responsibilities? Any good man will understand that.

But it also shouldn’t mean you can’t be flirtatious, seductive, and fun as well.

Personality Type 4 – The “Passive Introvert” woman

You keep it quiet. You stay reserved and let everyone else speak. You don’t take charge and ask questions. You leave that to someone else and hold back your real personality, sheltering in your introverted cocoon.

I know what it’s like in the introvert club. But if you wear that badge too much, you miss out. Flirting is about stretching what feels comfortable – putting a bit of yourself on the line, showing some of your weird and idiosyncratic character.

You could have incredibly sexy qualities, but if you go tortoise-shell in the first conversation, a guy may never get the chance to see them. When you hide away too often, it’s impossible to create the friction that is so essential to desire and chemistry.


So…here’s the question: can you shake off these personality traps and learn to flirt like a pro?


In fact, we have a killer new video coming tomorrow that’s going to well and truly break down the simplest formula for flirting possible.

For now, just know: you can never underestimate how much flirting will change your relationships – whether you’re single or in a couple, there’s nothing more important for keeping attraction with a guy.

If you’re stuck in any of the gears above, just make a note of it. It’s important to know where your sticking points are, or else they’ll become a pattern you repeat over and over again.

Then, tomorrow, Matt’s going to show you the simplest way to break through these self-limiting personality-types and finally use the best tools of flirting.

For now, I’d love to hear your thoughts on this – what makes flirting difficult for you?

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5 Replies to “Four BIG Flirting Mistakes That Are Holding You Back With Men…”

  • I think flirting is difficult for me in not sounding too cheesy. Tom Cruise was on a very well known British chat show recently and his Sweedish lady co-star was recounting a story whereby he’d kinda flirted with her in one of their first scenes. He was laughing, as he does he’s so personable, and saying No I could not have said that, it’s so cheesy. If you’re him you can probably get away with it.
    When you have chemistry and a little bit of knowledge of a person I find it easy to be witty and flirty but when it’s cold and the person is a relative stranger it’s hard to know where to start.

  • Ok,according to this I’m a pro. No, but I’m not shy to show my personality. I would be a little shy If the man is totally is my typ,but I would play that out as being a natural response because we click. So, I’m not an introvert,totally don’t think work is most important.I’m definitely not too jocky(omg how much I reject that!). I love to laugh,but I prefer intelligence,for sure. The mother behaviour is really ridiculous,and I would only mention briefly I love to cook somewhere in between and move on.I would be nervous, but that’s normal-you cannot be too confident. Nice article Matthew-thanks!

  • Before surgery to remove ovarian cysts, I remember hating myself for not being able to flirt. Wow, I could be dead soon and I still don’t have courage to say more than hi and bye.
    Fear 1. He will find me completely digesting?
    Fear 2. I will look like the the fat woman in pirates of the Carribean that chases the skinny pirate, I will just end up looking like a fool?
    Fear 3. I’ll end up being slut shamed even though I’m barely talking to a guy?
    Fear 4. Since flirting does not come natural to me, and I was taught to physical keep away from men, I feel I set myself up for disrespect, and put myself in a disadvantaged relationship where someone just playing a con just to use me?

  • I’m always thinking that if I flirt with a guy that hasn’t made the first move, I can come across as desperate or needy . When I go out on dates I banter a lot with guys and sometimes that just leaves me in the “easygoing just wants sex” woman category …

  • What about old age? Should you be flirty by the way that is “FUN”. Or just let your hair go grey and accept. The fire is burning up. Damn its hard for me to accept. Oh well. Tortoise Shell it is. Darn! On the bright side nobody has to Accept Me. So the Dream Lives On. Yeah

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