It’s a way to get to know someone better, so no, it’s not weird. Just base your questions around the flow of your relationship. If you two are a bit kinky/flirty, then feel free to ask more sexually charged questions like what their favorite positions are. Otherwise, stick to basic things like where do you see yourself in 5 years or other get-to-know-you type of questions. If you want, ask things that you find to be dealbreakers, like their religious views or what their stance is on controversial political topics.
No. I usually enjoy it. By the way, isn't twenty questions the game where you have to figure out what the other person is thinking of in twenty questions or less? I assumed you meant just asking each other questions about yourselves. I've called it truth or truth before. Maybe twenty questions can mean either one.
I had no problem before, used it to get to know the girl I'm seeing and I'm 23. Just seemed an easy and fun way to get to know each other as both of us complained that we knew nothing about each other. Played that and after a couple of hours I knew more about her than the majority of her friends
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I do it all the time. It's about as perfect a setup as possible for that purpose
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