3 Ways To Challenge A Guy Without Turning Him Off

This is article #37 to be published on the Get The Guy blog from my brother Stephen. Steve helped co-write the Get The Guy book and is a wealth of knowledge on dating and relationships.

(Photo: Stuart Mudie)

Enter Stephen

Be Challenging.

You hear this mantra everywhere. But it’s trickier to get right than most women imagine.

Many women take it completely the wrong way. For example:

  • Some women think challenging means being combative: they fight with a guy on everything, and he ends up becoming defensive and hides in his shell.
  • Some women think challenging means agitating him: they tease and make fun of a guy relentlessly, to the point of looking like his bratty sister.
  • Some women think challenging means never showing admiration: They act so aloof and icy cold that he gives up and moves onto someone who wants to listen to what he has to say.

The truth is, ‘being challenging’ doesn’t mean putting up obstacles he has to get over. It means being exceptional enough that he wants to live up to your standard.

So in the name of clearing up some confusion, here are the top 3 mistakes women make when trying to be challenging, and what to do instead:

Mistake No. 1 – Never being impressed by him

“Oh, really, you have a masters degree in literature? Yea, loads of my friends did that. They’re all broke now, there’s no money in a humanities degree, right?”.

You might think you’re just sharing an opinion, or making a light joke at his expense, and that may be true. BUT DON’T SAY IT!

But aren’t you just being honest? Maybe. But you’re being honest in a way that directly says “I don’t value something you invested your heart and soul into”, which translates in his mind to: “I don’t value what you do.”

Whether you’re just trying to act unfazed, or are spilling your brutally honest opinion, this is only going to make a guy feel worth less than his best around you and drive  him want to be around someone who actually values his accomplishments.

What To Do Instead: Tell him what kind of traits you do admire in a man.

For the guy who just got his masters degree, or works on any passion project, even if you have reservations about the particular field, the least you can do is show that you admire the qualities it displays, whether it’s the pursuit of knowledge, the bravery to follow his passion, or simply the fact that he’s pushing himself to achieve something difficult.

Another thing you can do to be challenging here is tell him what kind of traits do impress you in a guy. So if he asks you about sports, after you tell him what you play, you can say: “Physical activity is so important to me. I love a guy who makes time to keep fit.”

This way, even if he’s not living up to a certain standard right now, you are subconsciously telling him: “I’m not impossible to impress, but I do have certain standards”.

Mistake No. 2: Mocking him in front of others

Only a rookie tries to be challenging by knocking a guy’s ego in front of others.

The Male Ego is not a muscle. If you break it down, it doesn’t get stronger. It’s more like a nervous cat. If you’re friendly and care for it, he’ll become completely attached to you – if you scare it, he’ll run to someone else.

What To Do Instead: Display integrity in front of others

I’m not saying you can’t make jokes about him in company, but you never want to make him a rival. Otherwise he’s going to become defensive and close up in your presence.

The best middle ground is to show integrity. This means vocalizing when you disagree with him and not following whatever he thinks, but also showing a respect for his opinion and always laughing with him, not at him.

E.g. You both joking together about the weird staff in the bar you’re in and your secret fear they might be robots posing as humans – Cute.

You making him sweat by poking fun of every story he tells – Not Cute.

Mistake No. 3: Actively being disinterested or shunning him

This is textbook ‘hard-to-get’ behaviour: I like you so I’m going to be aloof and stage regular disappearing acts so that you’ll come and pursue me.

Trying to shun a guy will only either (a) confuse him, or (b) attract the worst, most persistent guys in the room.

What To Do Instead: Pay Attention To Everyone

If you’re in a group conversation and want to seem high value and challenging, the best thing you can do is be the person who talks to everyone in the group.

When you’re able to do this, it gives the impression that you’re the social hub, which has the benefit of both making you seem non-needy (since you’re not zoning in on one person), whilst also making you seem approachable since you’re not excluding anyone from the conversation.

Added bonus: When you pay attention to others, it makes those times when you guide your attention back to him feel all the more special and exciting.

*     *     *     *     *     *     *     *     *     *     *    *

The best thing about the three techniques above is that they give you power and influence over the way a guy feels, without you having to play games or be fake.

Matt and I have always resisted the hard-to-get approach, not only because it leads you to pretend , but simply because, as you can see above, it so seldom works!

With these alternative techniques, you get to do the opposite or hard-to-get: Instead of using a fake challenge to appear high value, you are being high value and making yourself a challenge in the process.

What are your thoughts? Do you think playing hard-to-get ever works? Let me know in the comments below!


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45 Replies to “3 Ways To Challenge A Guy Without Turning Him Off”

  • Stephen,
    thank you so much for this post which I consider one of your finest ever!!! A cordial thank you for bringing up this topic! Its so important and totally relevant. I am very competitive by nature … and sometimes get carried away too.

    Thank you for reminding me that men have feelings too :))
    All the best,

      1. Stephen,

        Very well thought out article as always. I just have one thing I want to point out regarding the 3rd point. From my experience, I never played hard to get thing ever, it’s childish. But I have tried to avoid/shun a certain guy over & over again even though I was extremely interested and like him. It’s the best thing to do when I knew he was a player who knew about my feelings but tried to act friendly and genuine. I still couldn’t help but continue to have feelings for him but to protect myself I so actively avoided him (we had to be in the same place often). Sometimes, it’s actually far from acting hard to get (as many would interpret the situation) but it’s being exposed and unreciprocated and saving myself from heartbreak by an insensitive player who can take advantage of my real feelings. Do you have any different thoughts on what’s the best way to behave in this kind of situation? Thanks xx

  • I recently had a message from an old boyfriend from University who was sitting in his office bored and decided to look at my Facebook page. I get, ‘Get the Guy?! You have got to be JOKING. If you have to resort to that, then the world has gone completely mad.
    I have learnt so much from you and Matt. Especially for me, when as you mention here, about the Male ego. In the past I have not treated it with the kid gloves it has needed and I actually think it can make or break a relationship.
    Of course I don’t think playing hard to get works. But it is a fine line between caving in to the others wants or needs and yet maintaining your own identity as a high value woman. There are times this is easier than others and I think it really pays to stop and think sometimes how you are going to approach such a situation.
    Also by making a comment that slams someone’s achievements or their passions down is all they are going to remember. It will cut deep. All the nice comments and compliments will go out the window. Your efforts will have been for nothing.
    It’s interesting when you say does it ever work? How can it, when as Matt always tells us, we should like people that like us. Why would we then be attracted or impressed by a person being aloof or mocking?
    Many thanks again, very thought provoking article as ever.
    Hope you are well, Kathryn x

    1. “It is a fine line between caving in to the others wants or needs and yet maintaining your own identity as a high value woman.” – very true Kathryn, well said!

      Thanks for your lovely comments, it’s interesting to see many people on here talking about their history fragile male ego – seems people have the same experience of damaging it and finding out the hard way lol

      Hope you’re well,

      Stephen x

  • Stephen, these kinds of behaviors don’t work on either sex.

    I don’t personally act this way and I’m surprised to hear that women act challenging in this manner because I haven’t seen this at all.

    In fact, I have seen men display these kinds of behaviors towards me–arguing too much, being combative, never showing admiration, agitating or teasing me too much. This is the reason why they aren’t in my life.

    1) I’m pretty good about showing admiration to a man when he really deserves it. But I see that men often act entitled and expect every woman to be impressed by them–even when they aren’t being all that impressive.
    That said, I do admit I have made mistakes by accidentally mocking someone’s passions or hurting a guy’s ego. But it was a genuine mistake on my part and I’m more careful now, with both men and women.
    Men have sometimes insulted my intelligence/passions and I don’t take it lightly. Usually it comes in the form of some condescending comments or advice that assumes I’m somehow stupid/immature. For me it results in an automatic loss of interest.

    2) I’m not sure why mocking is even on the list. Seriously, who likes that? It is pretty obvious not to do that with someone you actually LIKE!
    I think sometimes people end up making insensitive jokes without realizing its effects. For me this is horrifying and I would never do that to a guy I loved. For me it is a matter of basic loyalty. Even if I disagree with a guy in private–I would defend him fiercely in public. Laughing AT him, unless he is deliberating acting like a joker–is unthinkable!
    I haven’t seen any women actively mock guys. Mostly, I see them stroking their egos.
    However, I have seen a lot of PUAs teach that to men to attract beautiful women. Some of these men don’t get the difference between light teasing that is a compliment and teasing that sounds like an insult, especially to a woman who may be unsure of herself.
    Personally speaking, I’ve been laughed at and teased because of my height (only 5’0″). Usually I assume these guys don’t like me but and if any of these guys even hint at any romantic interest, they get a cold shoulder. I’m pretty sensitive about it.

    3) Again, I’m not sure who actually does this. Why would anyone actively shun someone they like and want to get to know? I think some people just take things too far in being aloof because they are worried about appearing needy and clingy. And then there are those who want to play hard to get–which is just stupid.
    Personally, I tend to “shun” those who “shun” me. For me it is an automatic reaction. I tend to respond well to guys who seek me out.

    You’ve suggested talking to everyone–but really, does that help when you like someone? Of course, it might be too much to just hone in on the one you like but just being friendly to “everyone” indicates that you are generally friendly and have no special interest in someone. This is just confusing. I’ve had guys do that to me and I just got confused which girl they were really interested in.
    Stephen, I think it is very important to show special interest in the one you like without becoming fixated on them and overwhelming them. In the past, I responded best to guys who singled me out in some way. And when I singled out guys for attention in a group, they responded well to me. In all other cases where either of us tried to play cool –nothing happened.

    1. I was reading through your comment and I cringed at under your first point. You’ll compliment and appreciate a man when he deserves it? Guys are insecure. Those who talk big are the most insecure. I’m not saying you need to compliment everything but the drives under the action can be complemented. A guy can go off bragging about his car but what he wants to hear is that he has good taste and style. So he got a college degree- I value your dedication to education or so forth. Sure there are dicks but come on everyone deserves admiration.

      1. Yes, of course if someone has great style then I’ll definitely compliment him. If someone has worked hard for a degree or taken the road less travelled–that IS worthy of being complimented on. The drive or intention behind things do matter and are worthy.
        I agree, there is certainly something to admire in everybody.
        That goes for women too. A woman may not be beautiful but every woman has a certain feature worth admiring–pretty smile, soulful eyes–what have you! But do guys notice that? Do they go out of their way to make a woman feel beautiful in her own way? I haven’t seen it! All I see is guys rate women as an 8, 6.5, 10, say demeaning things about them and their individual body parts. Is that worth being complimented on–“wow you have such a discerning eye for beauty–just great taste in women.”
        I was talking about guys who fish for compliments when there really isn’t much to admire there. Yes, these guys are insecure and it is NOT MY JOB to make them feel better about themselves. Especially so if they cannot find anything to appreciate in others and think they are above everyone else.
        I’ve also met guys who want to show off at MY EXPENSE—finding things I cannot do or do not know and then trying to one-up me or lecturing me on how I can get “better” at these things. These guys don’t deserve anything but a cold shoulder.

      2. Oh and guys who brag about how many women they’ve been with? Is that worth complimenting? “yeah, wow you’re such a stud”. Of course women would just be called sluts for the same thing.

    2. Hey Kish!

      Thanks for these thoughtful comments as ever.

      (1) On your point about admiration, I don’t think it should be taken as fawning over a guy, it’s more just a basic principle of showing appreciation for what a guy does and being a positive presence instead of a constant critic.

      (2) You’d be surprised how many people still have the playground mentality of being mean and mocking someone they feel attracted to. Some women don’t realise they are doing it either and take ‘teasing’ to mean ‘making a guy look foolish’. It doesn’t work (shockingly).

      (3) I think when it comes to the matter of attention, it’s best to mix it up at first i.e. show a particular person special interest, then address everyone else, then go back to that person you have a connection with, then back to the room etc. My point was just to strike a nice balance, instead of doing either one too much. But you’re right, special interest is important at some point to establish a deeper attraction and connection, though it’s good to show you’re capable of working a room and being sociable too.

      All best, :)

      Stephen x

  • Completely agree. I was grudgingly doing the cold should the past few years, cause one book, ahem, that many quoted, made me feel like I had to just sit there and be cute and do nothing, lest I be deemed desperate and foolish.
    I would say that these particular suggestions really do help me a lot and I don’t need to do any approaching, as I simply enjoy socializing with anyone and getting over my shyness, more guys approach me and don’t see me as scary or something that I’m not; double win for me! :)
    I’ve had more guys approach me that past few months than I had in a many years.

    1. Awesome Debra! I love hearing people who give up the cold shoulder and are better off for it. Being cold makes you powerless and miserable.

      Thanks for the comment x

  • Steve, these are all great tips, and they work!

    I enjoy your posts; like that you kept it short, keeps our attention (women like to get to the point:).


  • The amount of weirdness I feel for you Husseys is only surpassed by the amount of admiration for your humor, intelligence, sensitivity and mysteriousness

  • I find these to be the old school mentality and also very European a.k.a. If you love or like somebody, make sure to beat their ass and let them know how things are to be done. I believe that this approach worked in the past bu it’s now evolved to a more secure, women-empowered dynamic.

    It’s great to have a constant reinforcement of the new ways of dating and relationship momentum because at time I find -selfish me – myself caught in the old school mentality where the little girl inside of me gets critical and bitchy. I guess we all have our demons moments :))

    Thank you for this article!

    Could you maybe write or make a video about male insecurities? I’m finding these to be hilarious (clearly from personal experience) and now I get it why men complain about female insecurities- they are tres ridiculous!

    Dina (tdot)

  • “Keep away from people who try to belittle your ambitions. Small people always do that, but the really great make you feel that you, too, can become great.” ~Mark Twain

    Thanks for another great article.

    1. Addition: In reference to your question “Do you think playing hard-to-get ever works?” I think it does work in some cultures. For example, in machista cultures where man is the dominant one and feels like he always has to prove that he is a real man, the women are expected to behave in conservative ways. No matter how lady-like you look, if you jump into bed with a machista guy right away, you will be labeled. Certain believes are just are ingrained in these guys’ heads and it over powers their romantic feelings. They like girls who play hard-to-get.

      Whereas, in countries like England, Ireland, Norway, France men have much more evolved mind-sets. They judge a woman based on her personality. If she comes across like a strong woman who is enjoying her body and doesn’t need anyone’s approval, then guys respect that. I think you guys can sense this kind of woman very well. She might not be hard-to-get but she will be hard-to-forget, so the guy will go back to spend more and more time with her.

      American men are not as open-minded as European men. You might meet some really evolved ones in big cities if you are lucky (NY, Chicago, San Francisco, LA) but the rest is quite traditional when it comes to relationships. They can’t look at the big picture. They don’t have much people experience and they are usually too shallow to read a strong woman properly. If only they were as great as those idealized boy friends or husbands portrayed in Hollywood movies. So, I would say it depends on the person and his background. But at the end of the day, you attract what you are. If you are a shallow guy, you attract a shallow woman who likes to play games. Problem solved. :) I just have a lot of people experience  xxxx

      1. I love your distinction between hard-to-get and hard-to-forget! What a great line.

        I think the problem is hard-to-get wears off so quickly. One the guy has the girl (or vice versa) the chase is over and all that matters is how special and valuable that person is, and if they have nothing about them other than playing games, then they soon get found out. So it’s a short-term strategy that makes no-one happy in the long-term, and distracts from the more crucial work of actually being a challenge by living an extraordinary and fulfilling life.

        Thanks for sharing your thoughts on this Kiraz,

        Steve x

  • Hi stephen,
    we, women have to pay attention to everything :
    be hard-to-get, but not too much, and pay attention to him, but not too much, you have to be authentic, but you have to change your looks,
    don’t be impressed by him, but not too much,
    you have to be honest but mysterious, you have to be so, but not too much, etc…. Really hard to be a woman, in these days. she has to pay attention to everything about the man she is about to date (potential dates)!
    all “this paying attention” denote a form of neediness (even if : “pay attention not to be needy, this is repelent to a man”)

    1. Hi rima,

      I don’t think it has to be so overwhelming as you say. It’s just about following certain principles about being high value and not playing games. I try to give plenty of examples so you can see this idea in action, but they are just there to help rather than to confuse.

      I think you’re right though, that a lot of it is about balancing certain qualities i.e. showing him attention/affection but NOT being needy. It’s a matter of getting the calibration right, and this can be tricky, which is why we all make mistakes so much when we get it wrong!

      But more importantly, I find when you feel confident and happy internally you begin to instinctively know how to respond in an authentic and powerful way, so working on your inner confidence is always the most important part of attraction.


      Stephen x

      1. You go on about not game playing but it is what you advocate! Also there are times when everyone gets insecure and needy and needs reassurance that’s human you shouldn’t be afraid to ask your man for that.

  • Yes I agree with it all! I realised that I had subconsciously been doing your third suggestion (paying attention to everyone) and it really works – on me as well as for me! It is good to see a guy able to get on with loads of people and display that social value – but always make the effort to come back to me or be receptive if I go over. I guess the same must go for girls. The acting disinterested/shunning thing is the oldest, lamest but most common thing I see all around me!

    1. Thanks Teresa. It’s always sexy when a woman is able to hold the room and then suddenly gives you the attention. It shows her confidence, sociability and makes you feel special at the same time.

      Steve x

  • I don’t agree with playing games… It surely isn’t my thing! However I do have issues knowing how and when to be the one who makes a move, usually the guys that I like the most seem to have a great time when we’re on a date but are not any good at texting or talking on the phone and it’s not like we never see each other again, it’s just that it’s kind of a “face-to-face thing” or nothing at all… It has happened to me a couple of times and it’s really hard ’cause I’d love to talk more and get to know them even if we can meet up so frequently but don’t know how to approach the issue, I don’t want to seem desperate or overwhelming by being the one who always starts conversations… (BTW I’m latin and moved to Europe, people here is sooooo different -much colder and distant- from what I’m used to so dating has become kind of frustrating for me here)

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  • Awesome article as always Stephen. I see so many women out there making all of these classic mistakes. I know I have been guilty of some of these things in the past and didn’t even realize it. You are so good at clearing up confusion. I love your suggestions. It’s always great to get perspective about how men feel. Sometimes we forget that men have feelings too.

  • Somehow that “hard to get” thing did worked, well at least in my case and considering our culture… :) It did for so many years with one guy,he adjusted…i did too,but most of the time it was him-never realized that i was the one “killing him softly” lol-so it did happen (the break up) Which i initiated and assumed would help him to commit himself to me….it was most likely a need that i did not know how to relay :)

    Point? It may work but it will not lead you to where you must be heading…it will Just bring you to the same place, the same state & the chasing…happy but not happier.lol, you’re both doin good but not at your best-until, one of you or both of you will give up on the relationship- coz’ you were both unsatisfied.lesson learned? mistake #3 must really be avoided while not being “clingy” or i guess it’s really knowing his language and how to say your need in the right way.

    Sorry such a messy thought:).i could not just admit that i did this 3 mistakes.lol and i am guilty…but i am learning ;) Haha

    1. Just to support all your thoughts Says, i did this all too… after a week this “hard to get” works but your giving him a distance and thinking that “is there something wrong with me?” or “she’s the same like other girls who wants to be chase”.

      Sometimes he needs to feel that he is also important to you,
      i know it sounds that you’re the needy but it do works also.

      :) very interesting topic

  • Weirdly, I can’t relate to this post at all.. As much as I wanted to, but reality has shown me different..
    I learned the hard way:
    Guys mostly don’t approach you because they ‘like’ you, but because they wanna get laid – I think they might have a much better chance by showing that honestly.
    Also I’m a little pissed off by the whole ‘fragile male ego’-thing, which seems to be our responsibility as women to maintain – even if it’s a stranger we just met.
    I really DO like what you guys do here on the blog, it’s amazing and strengthening-BUT taking so much advise when we should be setting our own rules and standards to be taken serious (and being attractive) might be contradictory.
    Show a man you need him, but don’t be needy.
    Show him he’s special but don’t depend on him, i.e. you can always replace him.
    Maybe I have a real life and am not just a showcase..
    We as women shall not need a man’s reassurance; any kind of insecurity is unattractive – BUT always make sure you strengthen a man’s ego??
    Because he’s fragile and needs it?
    I don’t think I’d be a woman a man wants to live up to if I behave this way, flattering him like a fan.
    How does it fit with a man being interested in me? Maybe he’s just out to get his ego pushed.
    What stuck to me was a phrase I heard here that went: don’t like a guy for who he is in general but who he is for you(=towards you)

    I mean when a guy is just talking about himself and I play the cheerleader, it gets dull – and I’m surely not feeling like he’s interested.
    Being an admirer is, for most men, just boring – and it’s not a good trait to be impressed too much, I really got to learn that it’s no good!
    I found from my own experience, quiet shockingly, that the girls who were the least impressed, talked a lot about themselves and, yes: made most fun of the guys, somehow ignoring, talking them down and teasing, were the ones they tried to get.
    Sounds childish but that’s life, I guess.
    I found those girls have it much easier, guys would never even accuse them of hurting them/not being there for them as they would with a nice girl – they would just put their heads down and try harder, wooing for her to look in his direction.
    Who wants to be ‘chosen’ for being the NICE GIRL, because you’re no trouble, finally don’t have an opinion on your own, or surely never make a man doubt himself?

    Maybe not the best criteria to be chosen as a girlfriend – I might have made it all right then – but it surely wouldn’t feel right for ME.
    A lot of guys, I found, have a hurtfully wrong image about women nowadays: they believe – and even told me kind of cynical – that we women have it easy: we always have someone taking care of us, if we don’t know how something works surely with a smile somebody shows us, if we’re sad we get cuddled, and we have people doing stuff for us.. well surely not by those guys.
    All the love and applause to the women who lead this kind of life, wished I was there as well;)
    But I can’t make up for any mean girls a guy has encountered in his life, or some he just thinks had so many benefits- it wasn’t me! so..
    When guys assume this of me, I wish at least they were right. I had nothing being done for me – may be my fault, if they already assume it I might be just too stupid to make my charm play for me. I might even take it as a compliment that I look good enough that guys would do all sort of stuff for me – but it hasn’t been my reality yet.
    Maybe I’m not enough selfish, or assured, haven’t learned it – or it’s just not the world we’re living in today, not sure about that.
    Fact is I haven’t had it easy myself – where is the guy stroking my ego?
    I might need it and deserve it as much! :) Women have egos too.
    The most admired ones even by men, sometimes in secret, are the ones who are proud and not submissive.
    So one must be careful with this advice, not to attract a depending, selfish mama’s boy (yep sounds mean.. but they exist) – maybe it’s a bit demeaning for a woman who had to get it all herself, to make sure she’s never ‘competing’ with a man?
    Is that my only job.. where’s the fun for me?
    Maybe she has a field where she’s better (I hope so! Finally that’s what a guy wants isn’t it? We might have some ambitions in our lives too)
    If he can’t handle or admire that he might need a time machine.
    I once played pool with a guy and I won – I wasn’t even being inflated by it as he might have been, of course – he never wanted to play with me again.
    The lesson? Tell me.

    I found if I’m talking to everyone.. well it might be liberating for me, if I get lots of attention. But I found if I guy is into me but doesn’t show it and I behave this way he gets jealous even though he has no right to it at that point at all, or simply gives up instead of chasing – wrong guy?
    One problem of mine, I admit, is you surely need lots of confidence to pull that off! Like talking to everyone, showing him some interest, go off again – I’m not sure where I’ll ever get this confidence from.

    1. HOW GOOD is this comment! Love it!

      But I’m not even sure to say whether you’re right or not. Like both points make sense (the article and your comment). I mean, stroking a guys ego all the time – but not too much of course – is one hell of a job! und why is noone stroking my ego? Like you said, we have egos too! I never had such guy but a friend of mine did and then she left him because he was all cherish about her and talking good about her too much. So she left! crazy world :D

  • A guy friend once told me I wasn’t “easy”. As we
    are only good friends, I wasn’t sure what he meant. I think I will take it as a compliment.

  • Hello, I have a question about a guy I would like to get to know but not sure how. He is in my family. He is like a friend to me. I thanked him for something and he replied, he told me about some of his interest like hobbies and commented on an article about science I sent to him. He seems to like me but has not shown too much. He did not contact me nor did I for few weeks now. I don’t ask guys out and don’t know how to possibly try to get to know him or whether to even email him again and what to say? I wanted to email him and see if he replies not sure what to say? He thinks women that he dated wanted him for his job or money but it never came across or maybe he doesn’t feel anything to think about possibly getting to know me or maybe doesn’t want too. Anyhow, I am understanding and cool either way, just wanted one chance to see. Please help me.

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