I am in my early 30's, a rural gay who has never had a gay friend in his life. Most of my friends have been straight men. With just about every one of them I can recall a time when I thought they might be interested. I was always too scared to make a move. As I got older I stopped giving a fuck and made a move/told them how I felt at every opportunity. I've had at least 7 straight friends politely reject me, 2 that said "someday when I'm ready", and 1 that rejected me at first but then eventually came out as bi to me in private and we have been fooling around ever since. I know that sounds like a lot but there's dozens more guys I regret not making a move on, including one who I caught looking at my dick once who has since passed away (that one hurts the most cause maybe I could have fixed him). It's a small chance you will get your desired outcome but I would rather try and fail than spend my life wondering what could have happened if I was a little more brave at the time. Tell him, anyone who is advising you not is speaking from the pain of being rejected or hurt by guys like this, and it's more likely than not he will hurt you too, but it's worth the risk I promise. I would rather live with the pain of rejection than the torture of wondering what if. Keep us updated.