How do i tell him i like him?

Im 13 and i have a crush and my best guy friend. We are the same age and we have kissed before(while still friends) I used to have a crush on him in kindergarden and now i have a crush on him again!His mom LOVES me and he's always snuggling with me and has his arm around me. I want to tell him i like him, and maybe, possible go out with him. Is it bad for a girl to lead? Thanks :)