We weren't very close. Not friends, but not acquaintances either. He'd invite from time to time to his dance clubs and introduced me to his friend circle. At school, I noticed there was one cute girl in my social circle who was CRUSHING on this guy. At a houseparty of his she'd grind on him all night long. At the club she'd follow him everywhere. Same at school. Always hanging out around him.
I learned from a friend of mine that this dude would often lament about how he's never had a girlfriend (kissless virgin). He'd been shown interest several times in the past from various other girls, but he would just ignore them saying he was "not interested", only to end up regretting it later. I felt a certain pity for him, so I thought I could try to hook him up with this girl. She was giving him some very strong IOIs and this chump just couldn't see them. I had to act.
So I decide to message him one day about it and tell him that I've noticed that she liked him. He said "I know, we have a date set up on Friday". He said he liked her too. Out of curiosity, I've asked him if in the past two months he's made any move on her. NONE AT ALL. So I'm frank with him - I tell him to be smooth about it, but to get a k-close on this date. Guess what he does next..
He SCREENSHOTS the convo, sends it to the girl's best friend (who happens to be the most avid gossiper for miles), who ends up sending it to the girl in question and everybody in both her and my friend circles. Lots and lots of drama ensue about how I'm "objectifying women". I wouldn't normally mind but she was a latchkey to a lot of new girl friends. Now she's legit pissed at me to the extent that if I say a "hi" or try and start small-talk she ignores me.
I confronted this guy in a calm way, told him that what he did was not respectful and that he should learn about the concept of discretion. I told him not to do that again and wtf did he do? Stared in his phone screen the whole time and was like "uh-huh, yeah, sure, ok man". Told him the rest is up to him and if he fucked up, I wouldn't help him.
See, I tried to help a drowning man and ended up getting pulled down under. He's probably going to screw things up then start crying again about how he's a kissless virgin. The lesson here, gents: you can lead a horse to water, but you can't force it to drink. If you do you get a kick in the nuts.