What is the biggest "I shouldn't have said that" moment you've ever had RIGHT AFTER you said it?

uuughhh.

I was incredibly petty and just angry after my last girlfriend of four years broke up with me. I had some pretty severe depressive and temper problems at the time. There was another girl that I had become friends with while my girlfriend and I were dating, who was really attractive and did cause a bit of jealousy from my girlfriend. Lets call the friend 'amber'. So shortly after my girlfriend broke up with me I told her "oh hey cool, now I don't have to just fantasize about amber while fucking you"

That was just awful of me, and I felt so bad about it. That was almost four years ago, and my ex and I still haven't spoken more than one or two angry exchanges. Thankfully, I think I have grown up a lot, and wish I had the chance to apologize for it, but I'm not so sure I ever will since it has been made very clear that she wants nothing to do with me. (granted, not because of that one thing I said, but still)

/r/AskReddit Thread