How Being a Challenge May Hurt Your Dating Life

being a challenge and datingFor years, the concept of being a challenge in dating has been marketed to both men and women. It has been suggested by different dating advice sources that to be more desirable, you have to be a challenge. This means that you have to act like you are less available than you really are, harder to get a hold of, and are otherwise “hard to get.” While there is some degree of truth to that, taking this idea of being a challenge too far might have an opposite effect. Not only will it suggest that you are playing games, which most people with any dating experience are aware of, but you will also likely come across yourself as needy and desperate – desperate to raise your value by resorting to a rather extreme measures of making it look like you are more busy and less available than you actually are.

Being a Challenge Can Actually Make You Appear Desperate

Being desperate is an interesting term in the dating context. People often use it in reference to someone who is needy – someone who is eager to date or get into a relationship quickly and/or someone who has low standards and would rather be with just anyone, even someone they don’t really like, than being alone. Obviously, this quality is unattractive and is a major turn-off to both sexes.

However, there is another kind of desperation, which I believe is even more unattractive and damaging to a person’s dating and romantic life. This is the kind of desperation that you exude when you are not doing the things you want to and when you don’t show your romantic interest in another person simply because you are afraid of being perceived as desperate or interested. In other words – you are trying to be a challenge.

There are so many examples of this kind of desperation. A high school student is afraid to sit in class next to a girl that he likes because he is afraid that she and others will know that he likes her. The girl is afraid to make an eye contact with a guy at a bookstore because she doesn’t want him to know that she finds him attractive. A guy is not asking a girl out who has rejected him before, even though it’s clear to him that she changed her mind about him, because he is concerned that she will think of him as desperate. A woman texts or e-mails the guy she met instead of calling him because she doesn’t want to be too “forward” and be perceived as too interested.

The above situations mostly happen because people are somehow embarrassed of their romantic interest instead of being proud of it, and also because the idea of being a challenge when it comes to dating has been marketed to both men and women through just about every media source. Just about every dating and relationship book encourages both men and women to be a challenge and play hard to get for a reason or no reason whatsoever. Because of all that advice we often act as if it was some kind of crime to approach and start a conversation with someone, or even to make an eye contact with that attracted stranger who sits or stands across from you. We tend to forget that your interest in anyone, when expressed in a confident and respectful fashion, is a compliment to that person regardless of how he/she feels about you, and if they can’t recognize and respect that, be it accepting your advances or gracefully rejecting you, it’s their problem and not yours.

The Notion of Being a Challenge Should Not Stand Between You and What/Who You Want to Have in Your Life

You have been given the drive and the ability to want to be with a few specific people in this world for very particular and pre-determined reasons. It is nothing to be ashamed of. It would be a much greater problem if you weren’t attracted to anyone. You should not allow those who don’t quite know how to handle that power to either discount or discourage it in you by their negative reaction toward you. You are never desperate when you do what you want – when you take charge of your life and show initiative in your romantic interactions with other people.

Who do you think will get the job sooner – an applicant who sends in a resume, follows up by phone, and sends a thank-you letter after the interview, without being concerned about being too pushy, or another applicant who sends in his resume, and sits back waiting for the potential employer to pick his resume out of the hundred received and contact. Although comparing dating to looking for a job is not a perfect analogy, the point I am trying to make is that being passive when it comes to meeting people and dating is often as fruitless as being passive in job search.

Although a different kind of enthusiasm is required in dating, the bottom line is this: taking action and taking your own dating life into your own hands – be it showing interest the right way at the right time, or making it clear to the other person that you want to spend more time with them – is the way to go about improving your romantic life, and it’s not the same as being needy or desperate. Being a challenge has its time and place in flirting, courtship and dating, but taking the notion of being a challenge to an extreme can backfire and make anyone extremely unattractive, confused, or simply stuck-up.

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About practicalh

Practical, effective dating tips and relationship advice.
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  1. Thanks! 😉 That’s an interesting topic. I don’t know if I can write a whole book about that, but an article or a video will be coming in the near future.

  2. Thanks! As for the book, I think that a problem, for all of us “young male viewers”, is
    that we’re too inexperienced and primarily REACTIVE. We react to the problem after it has occurred. Then we ask for advice, articles, videos, but it is too late at that time.
    For example, in my last relationship my huge mistake was that I have not realized that my ex-girlfriend has become insecure and that she required reassurance from me.
    And I behaved in that moment like a “cold fish” and like I do not care. And since then, my relationship was like a plane that plunges and crushes in the end. There was nothing I could do after. If you could write a comprehensive book (about 300 pages) with all relevant stages of the attraction and the relationship we could act more proactively and we could anticipate what might happen, like a Leaders do. When you e.g. write about the topic of attraction you could just reference “Google PH How Being a Challenge May Hurt Your Dating Life.” That way, you could become unique on the market i think. And if you really do this, you could share with me 1% of your profit, you give a tip to your waiter, aren’t you? Hahahaha!

  3. Thank you, sir. Much appreciate your words and the idea. That would be a long term project but something I definitely consider doing. Closing the deal – this is the time when I would isolate the girl as they are a little embarrassed and self-conscious about giving their tel number in front of friends. Ideally, it would happen naturally. As you talk to the group, and focus on one of the girls, you would probably want to move a few steps away from the group or speak one on one with her. If things go well, and she is interested, then you will be talking to each other and the rest of the group will fade at least a for a few minutes. This is the time to ask her for her tel number and politely exit and let her get back to her friend. The one mistake that guys make is lingering around as long as possible in order to try to score the same night. This makes them come across as annoying quite often. There is no reason to linger around a girl you just met for 3 hours. Chances of sleeping with her the same night will always be relatively small compared to the chances of tiring her with your company, or saying something silly that will turn her off.

  4. Hello again, young male viewer here hahaha!
    Massive respect man, I did not expect you to make this video so fast.
    Just one more question. After approaching and speaking with a group, what do you think is the best way “to close the deal” and isolate a special girl from the group???
    It would be wonderful if you wrote a few examples for the final step.

    I’m glad you responded to my request. Every honor man! Here’s one more suggestion.
    You could write a book, a kind of coaching manual that gives the baseline knowledge of how to interact with women successfully, from the pick-up to the break-up. And you could reference your videos/articles throughout the book. Just a suggestion…

  5. Hey, there. Here is the video as per your request on approaching a girl when she is in a group:

  6. As always, Mickey – half glass full kinna guy. 😉

  7. What will probably happen is that a guy will approach a group of girls and they will just pile on him…and not in a good way.

  8. Thanks, sounds good. I will probably update the article and will also make a video and will embed it on the same page. I will let you know when it’s done, unless you are subscribed to my videos in which case you would of course be notified automatically.

  9. That’s it, that’s the topic! You could really expand on that. Your article is old almost a decade, I am sure that you gained a lot of experience in this period haha. I personally do not know anyone who is very successful when it comes to approaching girls in a group.
    Keep up the good work!

  10. Thanks for your kind words again. I think one of the reasons that I am more responsive, ironically, is because this is not my day job or main business. I really enjoy observing, analyzing and helping, regardless of whether a few of my programs and services swell.

    About hot v average girls. I would go even further – an average girl with great personality and skills in bed is going to be hot and hotter than a hot girl with a bad personalty or who doesn’t know what she is doing in bed. You are bringing up one common mistake that guys do – especially in bars and clubs – they look at the hottest and the sluttiest looking girls on the dance floor, not realizing that often wallflowers are better and even more sexual.

    About approaching girls in a group – I wrote an article about this a while ago but I will make a video about approaching in a group very soon:

  11. I think that there are 2 biggest problems for guys. 1) Dismissing in the start girls who look normal and chasing just the hot girls. We are not willing to give a chance to a normal girl but we are very disappointed when hot girls do not give us a chance. And normal girls perhaps have great personalities. I’m sorry that we are so strict when it comes to appearance and looks. 2) Focus on just one girl. You inevitably become needy and desperate if you’re all time focused only on that one special girl! And if she’s not interested and you are persistent. It’s like digging gold where there is no gold. You work hard, digging deeper and deeper, but still nothing. You become angry and disappointed because you worked SO HARD, but in vain, there is no gold and it will never be at that place. And then you give up dating.
    Your greatest quality is that you always reply!!! Believe me, I’ve followed several other “dating gurus.” But they never answered any of my comments! They just offered Live coaching and advertised their products. As if they are so busy and care only about money. Just one more question. Do you have an article/video about approaching girls when they are in a group??? If not, I encourage you to think about it. I think this topic is underestimated. I’ve always had problems when I had to approach the group and to meet a girl who is attractive to me…

  12. Thanks, I am glad you find the articles and videos on this site useful. I will be making more for sure. It’s a good strategy – you show your interest in so many ways, but if it’s clear that she is not interested, it’s time to move on, as the more persistent you are with the ones who are not interested, the more unattractive you will be to them. The “Notebook” kind of dynamics are very rare these days or might not even longer exist, so taking “no” for an answer is usually extremely ineffective or even counterproductive.

  13. It is important to say that I approached her first, and I helped her a lot at one exam. At that time I was not at all focused only on her. I approached and tried with 5-6 other girls (in this semester). But they all showed little or no interest, or they had a boyfriend. Only this girl was different, totally! It was not typical and an exception for me. Many times before I was very persistent with girls who were not interested, and I never got the chance. I only got the answers, “let’s just be friends, and you’re not my type.” I did not understand then why this is so. I read your articles and watched your videos a few years ago, it helped me a lot to look for and recognize real interest signs. I gave this girl a chance, although I challenged and tested her, and it was the best choice.
    Best Regards

  14. That’s a great story, Yudzin, but I would’t expect this to happen very often and wouldn’t count on women to be that forward and that persistent. It is still our job to to make interest known and to make a move. This doesn’t mean you have to beg or continue showing interest if the girl doesn’t, but the gender dynamics are still there.

  15. As I said, being a challenge, but not a jerk, is not bad at all if a woman is a goal getter. Here is a story with my ex girlfriend. We met at the university. She was attractive to me, but at that time I was not ready for a relationship. From the start I noticed that she was very available to me. She was always there. She even picked up one subject only because she wanted to see me. Once, while I was talking to her friend, she passed and said: “And when are you going to say Hi to me?” At that moment I knew that she was very interested. It was to me like she took the megaphone and she said to me “Come on, do something!” And I took that advantage. 🙂 I did not want to rush anywhere. I wanted to test her to see how far she will go. She sent me messages, called me to her friends house party. Even she waited me after class in order to travel together home by tram. Since I knew that she did not exercise very often, I invited her to run with me. And she ran 5 kilometers without a break (although she swore all the time that she will have her revenge haha, and after she reminded me in a relationship to all her past effort). I was impressed with her effort for me. She was so persistent and I gave her a chance, and I kissed her that day. I will never forget her…
    I just want to say how many women are willing to go far if they are very interested. That playing hard to get is not always a bad idea. And that we also need to test and challenge women!
    What are your thoughts A?

  16. That seems to be a lot to ask these days, in large part because a lot of people sadly believe that being normal and being boring is the same thing.

  17. Whatever happened to just being NORMAL???

  18. Thank you. I am glad you found this article helpful. Hopefully, it will help you adjust your mindset and behavior in away that will prevent you from sabotaging your own interactions and relationships with the opposite sex.

  19. This is a great article. Two months ago I met this guy who I felt I had an amazing connection with. I initially sent him a few text messages but he only responded to one. His phone was flat and I took his number. Anyhow, this man is still in my headspace. I've decided to give him a phone call and try one last time. I'm petrified but not acting on it one last time also makes me feel sick. He was really striking & not an average man. He also has come out of a 10 year relationship recently. I've developed a bad habit of not calling a guy & hiding under a SMS or email. I wish I had called him first time around. Talking is the better form of communication. I've been gutless for so long.

  20. To Andy101: I do have a problem to flirt myself. I have a relationship going on and I'm not going to stop because I'm a bad flirter. It depends on what you mean with flirting. You don't need to flirt all the time either. Just spend time together and have fun. Desperation is hard to explain. Just don't jump away when you see that girl you like. I did that the first time I saw that girl which is now my girlfriend.

    It's very very easy. If you want to get to know with a girl you don't have the guts to approach, then I can tell you what I did. You only need to say hello and keep saying it. When you have the chance to see her you don't want to be arrogant.

    I was so afraid every time I saw her. I made shortcuts every time I saw her. I jumped to find a place to hide away from her. Now I want you to understand that first impression is the start of saying hello. It's VERY easy. Believe me. Many other friends of mine did say to her that I liked her. That didn't ruin it. You can't trust anybody, I didn't expect that my friends said that I liked her because I thought they would not say it.

    Don't think that you can get away with a secret. You will be visible when you spend time together. I wanted to keep this secret myself and you can't get away with it. I didn't have anything to hide.

    You need to take your time in a relationship. Don't say something like: I love you. She won't say the same automatically. Only you. Wait till she says it. This is desperation on my side.

    It's not true about nice guys. Nice guys can be mean aswell. When you agree with all she says it's like talking to a wall. Nice guys?! It depends on what kind of person you are. Don't think that being a bad boy makes you a better man. Just be yourself.

    It's not a bad idea to sit beside a girl. You're not a sexual being, Mike. You're just a normal person just like the girl. Don't be scared, she will get used to it. I sit beside my girlfriend at school and we even play cards together. Sooner or later she will feel more comfortable about you. But it's just a start.

    Giving a woman a break is also a good plan when in a relationship. I totally agree. Girls need some time alone sometimes.

  21. I need your help. Question: how often should I hang out with a girl, and how much time should we spend together. And she is very shy and silent… I also said the first time I met her, I said that I like silence. She’s asked me if I want to be with her and go for a walk and we meet. Today I did something unusual. I sat beside her and asked how she is doing. Afterwards in the “Lunch“, me and her had planned to play cards. That went well and we talked a little bit. I won 2 times and I don’t know how that is for her but whatever… I hope this is interesting for you guys AND girls. I need your advice. I asked if I could hold her hand and we did. We were sitting and having eye contact constantly and I asked after I held her hand across the table, if I could kiss her hand. That was ok.
    I’ve might done some stupid things like complimenting her the wrong way… I have said to her that she is the most beautiful girl in the world and that she is not like other girls. I have also said she is naturally pretty. But, is complimenting a kind of seducement or something? It doesn’t make me feel better unless she find it a good compliment and her pupils get larger and they didn’t. She’s even asked me if I want to be together with her, and I said **yes, I’m very interested**. We’ve met each other more than 3 times and I have said that we need more time to get to know each other. And she said the same. I’ve held her hand last time, and we talk calmly and silently. I’m not that kind of guy who is very sarcastic, but I am kind. And girls don’t like kind guys? What is it with this *kind* thing?! God, help me please. Do we need the three S’s? Self-confident, sense of humour, and self-control.
    I need to know when to take the initiative. I take a lot of initiative. She does that aswell. I’m only 17 years old and I’ve met this naturally pretty girl on school. I said: I’m glad we meet each other. She said the same, and she agreed. I ask her questions like: Do you like when I hold your hand? Did you like when I complimented you? Don’t be scared. And she said: I don’t have a reason to be scared. First impression was good. A friend of mine said that she said she liked me. This is the first time I meet a girl I like and want to be together or still good *friends*. Time has not come that I can say we are together… Or how is this working? I have no idea.

  22. Spent the last 2 years trying to get to grips with my ex leaving me for someone else 2 weeks after a big engagement party. Trust and confidence are totally shot after that as it really did come out of the blue. I really want to get out of having a negative mindset, but the trouble is I've never been into dating casually, even less so now, so when I approach a girl I like, I'm aware of trying to mask this and I feel the weight of both loss and expectation.

  23. Thank you for writing this article. It really resonates! A lot of times (in my life) I have falling prey to this type of desperation. Consequently it has robbed me of a lot of opportunities for potential happiness and to have a more fulfilling life. I never looked at desperation in that way. It is truly a unique perspective. After reading this article I now have the permission to go after what I really want without apologizing.

  24. practicalhappiness.c

    Hi, Walter. Interesting approach, but… perhaps it's a good idea to give a woman a break. There are different reasons why a woman might not be interested – from being in a wrong place at the wrong time, to having recently break up with someone and many other reasons. I am not sure if we can assume a whole lot about a woman's judgment in other things just based on that alone…

  25. Great advice as usual.

    I don't approach women the second time who have turned me down for the folowing reason:

    If they so misjudged my value before, how can I trust their opinion on really important things?

  26. This happened to me recently with a girl in an adult evening class. I was ashamed of approaching her, but then my issues are somewhat different. My parents were repressed about sex, and they never treated relationships as a normal subject. The problem with people seeing me pursuing a woman in a class is that I am then perceived as a sexual being – the very irrational shame I have. For me this and the shame of rejection are completely different.

    It's interesting that woman can view guys as "creepy" if guys approach them in public, but that it is apparently socially acceptable to approach people in class, maybe even if they do not want us sitting at the same table as them. Or is it just me. Is there anything wrong with sitting at the same table as someone you do not know in class just to get to know them?

  27. practicalhappiness.c

    I understand, but this would only be a shame if the guy allows it to be. So what if the others go and tell the girl all that? I realize it's hard to have that much confidence that early on, and it might be too much to expect from someone as young as a high school student not to let it get to him. It of course also depends on the high school and how much "drama" there is in the environment you are in.

  28. i disagree with all my respect when you said about student afraid to do a move on girl in class.its not shame if others find out but its a shame after those people start telling things to the girl that makes her change her opinion about a guy and she actually does.The others will ruin it because they will go to the girl telling her that your in love with her and takes all the romance away.It happened to me twice at highschool.I dont know in college but in highschool its better to keep things secret.

  29. Great article. I believe that we have intuitive instincts for a reason-however-our culture often advises us against them. I think that the examples in your article clearly speak to that issue. (It can go the other way too, when people ignore the 'warning signs' that they are getting-and forge ahead anyway with negative results.


  30. I think this is quite true and have witnessed it firsthand with other people as well. I believe the reason behind this, as you said, is the fright of being rejected, too needy or revealing that they have attraction towards that individual. Well written article Arkady! Keep it up!.


  31. Great article. Dont get discouraged through a mannerless rejection. Nobody needs to be ashamed to approach somebody. It is completly normal to desire the other sex and when a girl or a guy has a problem with it then he or her had a wrong education. Remember when you approach or flirt with somebody you are doing something good to the other person and when you get a stupid reaction it is really not your fault. Moreover you can recognize very early that you should better stay away from this person. If somebody has a problem to flirt with you or approaching, you can be sure that a relationsship would be a horror.

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