Should I tell him or not? And if yes, HOW?

I've know this boy for like two and a half years and never really thought of him THAT way until the end of this past school year. He's a really funny guy and has a lot of friends. In fact he's friends with most everyone in our class. He came over and talked to my friends and I a lot this year at lunch and joked with us and stuff. one day at lunch he was joking around with a bunch of people and was talking about ways to ask people out and chose me as an example and dipped me and hugged me and all sorts of things. I started to fall over one day at lunch and he grabbed me and pulled me back up and made sure i was all the way up before he even started to let go. Another day he was talking about hugs and chose me for all the examples again and then just didn't let go and would turn me with him when he turned to talk to people. He did all this for a phase and would smile and wave at me in the hall and then he just kind of stopped. He didn't really talk to my friends and i as often and didn't acknowledge me in the hall way and then right the VERY end of the year he started with all of it again. Its really heart wrenching. I know he's had bad experiences with girls before and is not likely to start anything. I think its up to me and I probably wont see him again until August when school starts. Really the only contact I have with him is Facebook and we don't really talk a lot on there we only really comment on each others statuses ever once and a while. Help please? Its really hard for me to just "go for it" so please be more detailed! thanks!