I'm really sorry to hear about what happened to that guy, getting beaten up is awful. But I think Olly's situation is different because he didn't do this out of nowhere. Back in chapter 4, in a way that came natural in conversation, Olly said "“It’s not a prowl, it’s more like…what’s the worst thing that happens, even if I don’t know if a guy is into dudes…worst case they reject me and I’m embarrassed? Both Mack and Declan agreed with that and Declan went further by saying “I gotta broaden my strategy here, think more about doors opening that maybe I might not expect to…” This didn't guaranteed they'd be open to Olly making an advance, but I'd say it means they'd either say yes or reject him politely. Of course, if Olly got rejected once, he'd need to not make any further attempts with the same guy.