Should i tell him?

WEll there is this guy, we've been friends for a few years now and i think i like him. He's great funny we get along great, we text alot and i take a walk with him almost everynight. I'd really like to be somthing more wih him than friends but he dated my best friend. They are both over each other and are friends again but i'd still find it weird. People have been saying for years that we'd be good toghter but i don't really want to make the first move. What do i do?