I'm getting mixed signals about messing around

I'm struggling with someone

I feel like he hints at messing around because of how he touches me when I sleepover at his house but he never directly does anything

I don't know if he is just nervous about moving to fast or what

We are good friends and he is super sweet

I just don't know what to do because I feel like he isn't really meeting me in the middle and I'm nervous to initiate because last time I tried we made out only for it to not advance which I took as rejection. I started to realize I have feelings for him and I know he has feelings for me. I don't know what to do. But if I don't do anything I feel like nothing he going to happen. (He also struggles with anxiety, so I don't know if that's a main factor) but I don't feel totally comfortable communicating which I know I should but I feel like I just need some reassurance that he actually is hinting and he is just nervous, so I feel comfortable initiating.