It's pretty straight forward. These are the two basic ways which apply to being a challenge, without driving women away:
1. During a discussion, (in a group setting or 1:1) there will often be times when a women disagrees with you and when this happens, usually if a guy is attracted to a women and/or intimidated by her, he will cave to her disagreement and change his opinion. Also, a fair number of women are masters at employing shame when they disagree with you. They will look at you with a sneer of disgust and talk at you as if you crawled out from under a rock. This often elicits some sort of pre-programmed matriarchal response in men instilled from their mother's raising them in childhood and causes men to back-pedal and cave and change their opinion. Don't do that. You don't have to lash out in response - don't match their hostility.... instead, contrast it by saying something like, "Wow, I'm sorry that a simple difference of opinion causes you to react with such judgement and venom. Seems like you have some things to work out there," and be confident.
I usually just laugh it up and restake
What I said. It annoys me when they do that.
2. Questioning women is good, but there is a way you need to do it and you need to mix it with validation. Most guys will literally cut women off in the middle of something they are saying in order to say, "OMG WOW! YOU ARE INTO PHOTOGRAPHY?! THAT IS SO COOL!!!!!" Don't do that. Instead, think of it like this: "Be hard to impress, but give validation when you are impressed." So If she says, "I'm into photography," just look at her completely flatly and say, "why". That's an example of a good challenge. If her answer is, "I don't know, hehe, I just like it." That's a lame ass answer and deserves no flattery or validation from you so you just look at with a little bit of a confused grin. If she gives you a detailed explanation that really shows you something about who she is as a person and what makes her tick and what makes her wake up in the morning or motivates her or something else that you admire or respect, then you can light-up a bit and praise her for it with a compliment or acknowledgement etc. So you can't just challenge everything she says. Just don't be easy to impress, but don't be impossible to impress either.
I see, thanks