6 Things Every Woman Should Know About Flirting With Men

Stephen Hussey

One thing I’ve noticed about flirting is that everyone has a different image of it in their head.

Some people think of flirtation as very overtly sexual, like some movie cliché of bad innuendos and all-too-obvious attempts to make physical contact, whilst others think of flirting as little more than normal everyday conversation with a few extra jokes and smiles thrown in.

The truth lies somewhere in between.

Matthew Hussey - How to get the guy - Flirting -

To help finesse this delicate balance between making flirting too sexual or too mundane, I’ve written 6 phrases that sum up exactly what constitutes creating that moment between two people who recognize each other as someone of romantic interest, rather than just as a friend.

Check them out:

1. Flirting is…moving things forward

You can’t flirt by keeping things at 10mph and chugging along with basic questions.

For example:

Him: What job do you do?

Her: I’m in online marketing.

Him: Oh cool, I have a friend who does that.

Her: Awesome!

Him: Do you enjoy it?

Her: Yea it’s great because I can work wherever I want, but sometimes get bored of being at a laptop all day.

Him: Yea I can imagine.

We can see here that while things aren’t exactly going badly, they have no sign of moving anywhere interesting or even vaguely risky.

2. Flirting is about taking an extra step, even if it’s only 10% to begin with.

For example:

Her: I’m in online marketing.

Him: Oh cool, I have a friend who does that.

Her: Awesome!

Him: Do you enjoy it?

Her: Yea it’s great because I can work wherever I want, but sometimes get bored of being at a laptop all day.

Him: That’s perfect, my job’s flexible too. Maybe we should just both leave this country go to a beach somewhere in Brazil so we can at least work in paradise every day.

Her: I LOVE the sound of that. We need to get a lilo so we can float in the sea and sip cocktails while we work.

Him: Ok, but I warn you now. If you splash my laptop, you’re dead.

That’s just one example – yes it’s silly, but it’s an example that allows you to talk about the idea of you both together in the future, and allows you to explore a ton of other avenues of interesting conversation, instead of just talking about what jobs you both do.

3. Flirting is…showing someone you like them

Flirting is the moment the dial in two people’s heads flicks from a neutral ‘friend’ feeling to a positive feeling of attraction.

As I’ve mentioned in a previous post, but so many people get bogged down in trying to be witty and clever, or trying to boast about their own accomplishments, but they forget that at its most basic flirting should be a way to show someone you actually like them, or at least, showing that you find something IMPRESSIVE about them.

If you like his career choice, his ambition, or the fact he cooks Thai food and writes poetry in his spare time, tell him!

This is why I stress the importance of being impressable. Even just saying, “that’s so cool”, or “I love that”, or “I’m impressed. It’s great when a guy is ambitious/musical/adventurous” has such a powerful effect in terms of putting you on a guy’s radar.

4. Flirting is…creating a shared moment by connecting over things that excite you both

Flirting is a moment of connection and bonding, laced with some tension just to make it more exciting.

This is why asking deeper questions is generally conducive to more of these flirtatious moments.

For example, asking open-ended WHY questions, like finding out why a guy works in a particular profession, or asking him about his exciting dreams for the future creates a space in which you both open up and allow yourself to be vulnerable by revealing something personal.

The more you encourage connection (mixed with the right elements of teasing and playfulness, as in the dialogue above), the more you have a shared moment of flirtation.

5. Flirting is…putting yourself on the line (in small doses)

Flirting is sometimes just taking the little risks.

For example, he does a silly laugh and you say, “that laugh is so cute”, or “has anyone ever told you you have great dimples?”. Or you might say “that bracelet is gorgeous. Guys who wear jewellery are hot.”

Flirting is about peppering your conversation with these tiny tweaks that create even a second of tension and excitement. If you say it with a smile and eye contact, it’s that brief second that creates a moment he’ll remember after going home.

6. Flirting is…creating mystery and intrigue

Although being too coy can be annoying, flirting is also about holding something back for later.

That’s why the woman who is too sexual from the word go freaks men out. It’s like they are laying it all on the table and not giving him anything to pursue further.

There’s a line Matt says that I’ve always liked: Men live for the maybe.

Whilst I don’t think this should be a license for endless teasing, it does mean that at the beginning it’s always better to hint at things to come rather than be explicit.

For example, if you’re about to see a guy for a third date who you really like, and he texts you and joking about coming to your place afterwards, say something like, “Well, that depends entirely on how well dinner goes first…x ;)”.

That kind of coy teasing is better than something that heavily implies there’s definitely going to be something physical on the cards later.

Besides, keeping a guy guessing never hurt anyone.

Want to learn 59 more REALLY simple flirting techniques to get in a guy’s head and make him crazy for you?

Must Watch: ‘The Phrases That Make Men Beg to Be With You’


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20 Replies to “6 Things Every Woman Should Know About Flirting With Men”

  • I love that quote “guys live for the maybe.” That tells me so much. I get all tied up in the suggestions you make while in the moment, but that quote can cut through the fog with its simple directness! Thanks for all you two do! <3

  • Hi Stephen, oh this is very helpful to hear from your male perspective on flirting, thanks. Matt has mentioned the millimetre shift that can change an interaction.

    Recently, I was totally flirting with this guy but he’s terrible at flirting back and I don’t feel any “tension” but there are moments of investment from him. It’s very confusing as I can’t tell if he’s interested or just a terrible flirt like Ross from Friends (remember that episode). Cheers.

  • What do you do if the guy you’re flirting with is terrible at flirting or doesn’t even understand it is flirting?

    Btw, I haven’t had the best results with flirting–the way you’ve described it. It gets me guys who want attention and validation or flirts or players who want to date multiple women. Not the kind of guys I want to date.

  • Dating can be stressful for both sides- he may be worried his choice of place won’t fit your expectations, while you will spend hours wondering what to wear to look sexy, but not trashy, the ever so elusive “golden middle”. He may be afraid to talk about his job or hobby too much not to bore you, which you may interpret as him not having any passions. That’s why, don’t play games and share your thoughts whenever faced with ambiguity. For instance, when you are telling a story, after short introduction you can ask how much the other person is interested in this type of topics: “Once, I was performing a surgery on this guy who had a rod piercing through… actually, one second, how well can you take gruesome stories? Do you faint at the thought of blood?”. Keep it light, keep it open, and be positive. Being on your toes around somebody is exhausting so creating relaxed atmosphere whenever you are together will make him want to spend time with you.

  • Hello Stephen,
    Loving your flirting advice… Learning to step up my game in the past few weeks. Haven’t dated in over 20 years so I am way more than rusty! I have converted many chance meetings into more meaningful encounters than I can count! Joined a singles group 10 days ago and have been to a evening bonfire, a dance and a beach volleyball game! Used the tips to make plans for next weekend’s dance and possibly found a partner for a ballroom dancing class!!! Even had a man teach me to tie a bowtie after commenting on his!
    This has taken therapeutic communication to a new level! I am having fun meeting so many new men …. And seeing them in a new light!
    Thank you both!

  • Helpful! Still finding the balance between, “hmmm…too subtle, apparently…” & “does this smell like chloroform to you?” My mid-range could use some work. Le sigh…fortunately fortune favors the bold, I am indeed that.

  • I love this! When I read it, I felt like I could hear your voice saying the words and it made me smile. It’s so hard to find the right amount of flirtiness without crossing over into overly sexual. This helps :) Love the sample convos. Xo

  • I’m having a lot of trouble knowing if I’m giving a guy a “maybe” signal or a “yes” signal. Does this really matter? Is it really that cut and dry? I’m good at creating connections. (touch/saying something’s hot about him/asking funny/deeper/non fact finding questions). I am not sexual because I have certain religious beliefs regarding purity. But I am pretty flirty and make connections super easily. How do I know if I’m coming on too strong and not having enough mystery? Maybe I just won’t be mysterious – is that a bad thing?

  • I love the flirty/sassy Steve that I get to see every once in a while. :) Flirting is such a fun past time… especially when it is reciprocated in a way that makes your heart race!

    Maybe just a cable and cuddle? ;)



    1. OMG I so did not understand you properly when you said “a cable and a cuddle”…

      LOL. Oops.

      You ARE talking about cable television, correct?

  • as a guy i can say most of this advice is very useful, but the “men live for the maybe” part is subjective. I would like someone who is upfront and casual (cause I”m a total nerd lol) about the physical part of the relationship. I feel that when a woman plays “hard to get” it is frustrating and confusing for both of us. So when he says mabye he probably means don’t actually play hard to get just make seem that way slightly, a little bit (men are stupid we’ll think your just not interested or worse a self center bitch) sorry for rant

  • Whether or not a woman is flirting, try asking her a direct question which is somewhat personal (and I don’t mean about her sex life). If she hesitates, or dissembles, move on. You are being played.

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