[Serious] What's the hardest thing you ever had to say to someone?

Back when I was a dumb asshole kid in high school I was in a very lonely dark place. I was feeling desperate for any kind of human connection and intimacy. My good friend's longtime girlfriend came on to me and I was so lonely that we ended up hooking up before I even thought about it. I felt terrible about it afterwards and he eventually found out. He was way more understanding of where I was in my life and why I would do it than I could have ever asked him to be, and we even managed to save the friendship, but he didn't want to keep dating her and he told her that. She freaked out and threatened to cut herself and he was scared and didn't know what to do. So my only idea of how to take responsibility for the situation and make sure nothing happened was to call her mom, and explain that her daughter and I hooked up behind one of my closest friend's back, I didn't do it because I was romantically interested in her daughter (she asked), and that she was threatening to cut herself. The worst part was that all four of us had gotten food a week before, and her mother was an incredibly sweet lady that I now knew personally, and this was my second conversation with her ever. I was only sixteen back then. By far the most difficult/ uncomfortable conversation of my life.

/r/AskReddit Thread