Relationship advice

I have been hanging out with one of my best guy friends here lately and he has been so sweet to me in all that time.

A couple of weeks ago he put his arm around me on the bus (because I was feeling extremely sick with my acid reflux) He said "You got this sweetheart", and snuggled me in a way. He will talk to me about pretty much everything, and he is amazingly supportive to all my decisions.

He smokes and dips (which is not good, I might add) but anyway, he is VERY selfish when it comes to tobacco but he has actually offered it to me.

He is really the only guy that I am comfortable being around.

He flirts with me and steps on my shoes going down the halls at school. I really think that he is amazing, but I'm scared of rejection and/Or heartbreak because it has happened SO FREAKING MUCH !

I really believe he is an amazing guy and we are both pretty outgoing. We have many of the same interests and I really feel a connection between us.

I'm just scared to tell him that I like him.

Should I go for it and ask him out ?

If you all say 'yes I should', I'll tell him Monday.