One key element to attracting a woman and keeping her interested over time is to be challenging to her. However there are many ways in which you can be challenging and the ways that you will be challenging will change over time as you interact with her and on the personality of the woman you are interacting with.
Before I discuss different ways in which you can challenge her, let’s talk about why you need to be challenging. Most women who are even moderately attractive get a lot of attention from guys even if they might complain about not getting enough. They have gotten used to the idea that most men are interested in them just because of looks alone. However they are often most attracted to the guys that they are genuinely interested in who they are and that they feel they have to work for and pursue at least a little bit. As a general rule, the more attractive a woman is, or thinks she is, the more of a challenge you need to be to engage her interest.
Another reason for a challenge relates to a woman’s self-esteem, generally a woman with higher self-esteem and goals will need more of a challenge to get her interest and keep her interested over time.
As far as the kinds of challenges that you need to provide: when you first meet a woman one of the ways in which you can be a challenge is to actively demonstrate that you are not entirely interested with her until she has done some things to demonstrate that she is an interesting person besides being physically attractive.
1) Scarcity/ Physically unavailable
When you first meet a woman one of the first things you will want to do things that test and challenge her to find out what kind of person she is. There are many ways to do this, one way is to provide what is often called a false time constraint, i.e. “I can only stay a moment and then I have to get back to my friends,” accompanied by body language that shows you do not intend to stick around. A false time constraint does many things, although one of the reasons it is effective at generating interest is by making you a challenge, which will make them know that they have to be friendly and demonstrate interest in you or else you will not stay.
2) Tease her/ demonstrate disinterest mixed with interest
Another way to challenge her, especially during the first moments after meeting her is to playfully tease her and she will probably tease you back. The reason for this is to show that while you may be interested you are not just going to fall for her just because she is physically attractive and that you do not need her approval. The key here is to adjust and calibrate your teasing to her personality so that you are not hurtfully insulting her. A good guideline is to tease her about something that she would consider to be a strength rather than something she would be self-conscious about. Or do things like compare her to a little sister or friend. This challenges her to make you want her romantically and sexually.
3) Challenge her on qualities that do not involve her physical appearance
Other ways to be challenging include challenging her self-image in a way that includes presenting a personal quality that you look for in a woman. For example you could say something like “I like adventurous women, what is one of the most adventurous things you have ever done?” Some things to look for in her response include how much is she trying to impress you, as well as how genuinely interesting she seems to be. Some women might feel put on the spot and not know what to say, in which case you could share one of your stories first and recalibrate.
Remember to smile or mix in with a compliment when you tease. This will soften the impact of your words and convey a mixed message that is playful and positive while also keeping her guessing. With practice over time you will get better at this and also adapt to your personality and adapt to the personality and the mood of the woman you are talking to.
That is all for now in terms of initial challenges. I will also discuss more challenges that you can use later in the interaction as you escalate the interaction emotionally and sexually. Also learn how to be challenging in the context of a relationship too.