Verbal processing

In camp life I have about 4 people that I'm really close with. One of which is my boss. Who is really fun, wise, and I'm letting him see the real me. Last night, I told him about ham. That's crazy, we are friends, but I don't talk about things like that. It was good though. (And he told me that work shouldn't interfere with any dates and he will cover any shifts I need--great boss!) and tonight I talked about it with my closest camp friend. It's seems so real. This is so unlike me. I really need to step up and tell ham I'm wanting to date him. I don't know how to do that, in my head this conversation is a night hike setting. But, I don't know, I have never had to take back intentions like this. I hope he is interested in dating me, or else this is just a lot of buildup for nothing. I like to be around this guy, I could potentially lose it all, is it worth it? I sure hope so!