I made one really stupid mistake in college that sticks out. It left me with a misdemeanor that was since expunged from my record, but the news story can still be found pretty easily - it sucks to have to explain when I'm going through job interviews. I hate myself for that one. Another more recent regret is that I didn't work harder in a lot of different ways in my relationship that ended a couple weeks ago. It's hard not to dwell on the thought that if I had just done this or that, the relationship could've lasted a lot longer - if not for the rest of my life. That feeling of emptiness in the gut after a breakup is such a shitty thing to feel on a daily basis. I know it'll go away eventually but I'll be damned if it doesn't hurt like hell right now. Thanks for asking this though :) It feels good to let it out.