Replying to Encouraging My Friend’s Progression

I’m trying to get my one buddy to attempt more things in the park. He’s super chill, he always laps the park with us even though he doesn’t really hit anything. I just feel bad because I feel as if he’s getting bored. Last year I was trying to coach him through sliding a box and he hurt himself kinda bad, and he just seems to have fear of hitting features now.

Any ideas of how I could help him overcome his fears? Of course I can’t force him to do anything, but I know he would love progressing in the park