Should I ask him what he feels?

So I’ve been hanging around this guy lately and it’s awkward because he’s not very expressive of what he feels. He will put his hand on my knee and show affection that way, but I’ve initiated the kissing and hugs and such. I also told him I enjoy our that stuff. We also spend 3x together and we have only hung out in his car. I want to go on dates to learn more about him but I feel like he’s horrible at initiating things so I feel like I have to be the one to ask him to go places. I am fearful of rejection , but I feel like our hang outs have been awkward because I can’t read how he feels and it makes me put my guard up
Should I ask him what he feels?
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