What’s the most awkward position someone’s ever put you in?

Moved in with one of my closest friends and his girlfriend at the time. Later while her and I were driving home from lunch, she told me that she was going to break up with him and that she knew he might need me to talk to him. No big deal, we go to a friends house, have a few drinks and prepare to look for new apartments. Later one morning, we have woken up a bit early and were playing video games in the living room when one of the guys she had apparently been cheating with walks out of her room and out the front door. Not too long after, she finds out she has syphilis and doesn't know who she got it from but tells my friend he needs to get checked and that she is so, so sorry. He packs his stuff and moves into his parents place that night instead of waiting for us to find a place to live. I was now living with his ex-girl friend and her latest overweight boy-toy. When I finally moved out a week later, she thanked me for being civil but it took a lot out of me to not spit in her face.

/r/AskReddit Thread