Never know when to take the plunge and tell a boy I like him

Background info: 22 y/o gay man, sophomore in college. Ended a 4.5 year relationship in spring 2015 with a guy who encouraged me to distrust people and doubt my own feelings.I had several classes with a boy that I thought was cute and who I talked to a lot, in a kind of small-talk "how'd you do on that test? I bombed lol" way. Never really talked seriously, never asked if he was gay, never told him I thought he was cute--just normal friendly chat. That's fine, just like "ah well, it would've been nice to get to know him and tell him he's cute."Haven't seen him 6 months.He adds me on social media, talks about wanting to hang out, and that's where I am now. He added me about a week ago, chats happened intermittently.Mutual friend says he came out recently. Bang.So my problem. I told him we'd hang, with mutual friends, play games, etc. Basically being friendly. Great.But! I was thinking about talking to him, about telling him that I thought he was cute, and asking him out. And I get incredibly anxious. "Of course you can't. He just wants friends probably. You'll make him uncomfortable and then you won't even be friends." Tortured myself for a night.I know it's all about taking risks, when you like someone.But is there a way to tell when someone likes you more than just as friends?My anxieties rile up every time I think about it. And I get into decision paralysis, and things pass by.Help?