Why is he scared or careful asking?

[Anonymous]

Im talking to this guy and he's like really cautious asking questions i really dont get it. Like we getting along pretty well talk about anything. But then when he asks personal questions he takes it back and doesn't wanna make me uncomfortable. Does he want me to open up?

[dankstranger]

Sounds like he does. I was this way with a girl once. I wanted her to open up so we could have more intimate and personal conversations but didn't know how to do it without taking the risk of accidently stepping over a line.

Eventually one day we were at a coffee shop and she saw the tattoo on my arm that I had never discussed. She grabbed my arm and started tracing the tattoo with her finger and asked "what's this"

It shocked me a bit that she would break the touch barrier so rapidly and confidently. After that I completely shook the jitters out and returned the same level of confidence when asking questions and opening up.

He may be nervous about accidently poking a hot button issue for you, but he still wants to have those intimate opening up conversations. He's struggling with a way to start those conversations in a way that poses as little risk as possible.

Show him your ready for him by doing it to him. Break the touch barrier or ask a direct personal question. If uou show a bit of bravery he will probably then be ready to realize you aren't afraid of opening up and be ready to match your confidence.

[sensible27]

Sounds like me, I doubt he would mind if you opened up

[Asker]

Okay so why you so careful then dont get it like the questions aren't even that deep. I mean its personal but it isnt… okay is it that, you rather want me to tell you instead of asking?

[sensible27]

No, it's not that I'd rather have you tell me instead of asking. I don't expect you to be.. like that, it's appreciated of course that you can freely communicate whatever is on your mind. I don't really understand myself well enough, but I don't think I wanna hurt people or ask them something that makes them uncomfortable. It's possible he likes you and doesn't wanna lose you, I do it with almost everyone because it's be rude.. to just ask something that shouldn't be my buisness even if I'm something. Generally it's "can I ask something?"

Imagine you're going somewhere and you wanna move through a line, you would say excuse me no? It's just a part of the personality possibly, and it might reduce as the time goes on and he's more comfortable with you but I don't know if it'd ever go away (all away)

[Wise4myage]

Maybe he's said the wrong thing in past relationships and just wants to be cautious?

[Asker]

Maybe