My former best friend was dating secretly another guy who wasn't out of the closet yet. He'd have me and our two other roommates go wait in our rooms so he could sneak his anonymous lover into his room without us seeing his face and then we'd repeat the process when it was time for him to leave.
The awkward had only just begun though because we figured it out the identity of this mystery man. It was a guy we all knew and he had just broke it off with his long term girlfriend recently. Word spread fairly quickly through a series of drunken over sharing at parties and general gossip among our respective friend groups. Within about a week shit hit the fan, and we knew we had all fucked up. I myself, was too afraid to face my friend so I pretty much just floated around other people's places for two days so as to avoid having to talk to him. My other roommate had texted me saying he would handle it, to which agreed (HUGE MISTAKE HERE). This led to me being blamed for everything. When actually the only person I had shared anything with was another friend who was also my boss at the time, which was mainly because we both worked with the undercover lover's ex girlfriend who was an absolute inconsolable wreck after being dumped and I was confident he wouldn't tell anyone else. (Still not okay but definitely not equivalent to announcing it at a party or using it as a topic of conversation while you're trying to pick up women. Which what the other two roommates had done and therefore was blamed on me).
Now we reach the awkward climax.
Fast forward another week or two and I find myself at a sorority date party. Things have started settling down for the most part and I'm having a great time with my date. We were leaving the dance floor for a break and I hear a girl shout my name excitedly. "sparkyfrosh!". It's literally the now outed guys Ex girlfriend. She comes over says hi, hugs me, looking utterly depressed she depressed she asks me "Is my ex boyfriend gay?". After a series of uhhh and Whaaa, I lied and told her I didn't know and that she should talk to him about something like that. She responded with "(insert my bosses name) says you know!".
Luckily the date party still had another hour and a half left, all of which I spent dancing my date while repeatedly making incredibly awkward eye contact with the Ex who was dancing pretty much right next to us.
TL;DR unintentionally "outed" a guy my Best Friend/Roomate was seeing by telling my boss about it. Guys ex girlfriend asks me if her former boyfriend is gay at a formal date party. I lie and say I don't know. She responds by saying that my boss told her that I know. I self destruct. The End.