Told a guy I like him, what now?

Essentially I told this guy that I like him over text and he encouraged me to ask him out at prom (which is on the 27th of June); however, he kept reiterating that if he rejected me it'd build my confidence but also that wasn't him saying he would turn me down. He knows I like him so surely if he felt the same he wouldn't put me in an awkward spot and he'd take the initiative since he knows what my answer would be. That being said, wouldn't he have just turned me down when I first told him if he didn't feel the same? I asked him how he felt and he said he didn't know. Overall, I'm really confused and don't know where I stand, on top of that I've already asked him to hang out and told him to decide what we'll do so I'm not sure what he means by 'asking him out' – does he mean ask him to be my boyfriend? Sorry if this seems obvious but this isn't something I'm used to and I don't want to mess up. I want to go through with it since I think I'll regret not trying. I don't particularly want to bring this up with him again, I've been trying to give him space so he can make up his mind and also because I don't want to come across as overbearing. So what should I do?