What was your "I'm a real piece of shit" moment?

Broke up with a girl (let's call her Jenny) in July of my senior year, started dating a new girl about a year later (let's call her Sarah). Jenny tells me that she still loves me, I'm somewhat confused by this news. Things got weird and come Christmas I cheat on Sarah with Jenny. I don't tell Jenny I love her or anything, and proceed to manipulate things to the effect that Jenny and Sarah become best friends. I know Jenny has no self control when it comes to me so I sleep with her just often enough to keep her "on the hook". This goes on for about four years. Jenny eventually says she cant do it anymore, its fucking with her mental health etc. We stop the physical shenanigans but I maintain the emotional connection best I can. A few months ago Jenny tells me she's found someone else. I don't take it very well. Proceed to tell Jenny, after all these years of nothing, that I do in fact love her and that I'm going to leave Sarah for her. I said this knowing full well that it's not true, and although I was about to split with Sarah it had nothing to do with Jenny. My lie doesn't work initially but after about a month of really working on it Jenny "cracks" and while her boyfriend is overseas we end up fucking. As soon as I finish Jenny starts crying her eyes out. It was roughly at this point that I realised I am trash.

/r/AskReddit Thread