How can I tell my crush that I like him?

So I have a bit of a dilemma. I was friends with this guy for 3 years in high school. We never really hung out outside of school, but we do get along in our own way. We joke around and make fun of each other alot but it's all in good fun. Where it gets complicated is at the part where I began to like him. I'm not really sure if he's gay or not, but I think he gave me very strong hints of flirting that he would only do to me. For example, he loves to look at me whenever he can and for long periods of time too. And anytime I catch him staring, he either looks away quick or tries to make me laugh. When we were on the soccer team together, he said sometimes how he liked being in the position behind because he liked the "view". I swear he's an idiot lol. I don't remember much after graduation but I swear it was strong. The only reason why I didn't pursue him was:
1. I wasn't ready to come out yet. I went to a Christian high school, so you know...
2. He was kinda "homophobic". I put quotes because he only was around his friends and he would try his hardest to be as vocal as they were about it. I could tell he was just saving face. And even then, the loudest ones are the ones with internalized homophobia. However his friends aren't really gay tho. They were just ignorant idiots.

But anyway, 10 months have passed after graduation and I recently talked to him the other day over text. We again had our usual sarcastic, make fun of each other thing, but that was it. So i plan to actually have a normal conversation with him tomorrow asking him how he is and stuff although I'm not good at that. I feel like I'll run out of these to say/ask fast. He also kinda tends to send one-worded responses as well. Sorry but the real dilemma is that I really want to go out with this guy. But I just can't bring myself to tell him that I'm gay let alone tell him that I like him. I honestly haven't told anybody. I'm just scared of doing so. But what I do know is that I'll be the one who needs to make the first move and try. Even though he flirted with me alot, he would tend to get very shy around me as well. If anything were to happen, I'd have to be the one to act. He's sensitive, defensive, and shy: all similar traits that I share so I understand what he's going through (if my gut is right about all this). So what would be the best approach to this? I don't want to sound desperate, but I don't wanna be missing out on a relationship that could last forever... I hate love lol.