Most Helpful Guy
Most Helpful Girl
Well.. two come to mind.
The first is not really a day, but more like a few months. Dealing with the aftermath of my breakup over 3 years ago. Sexually assaulted by 2-3 friends + a taxi driver, getting cheated on by my ex, about a week after I had sex with him for the first time. All within a month or two.
Another is when I got into a really serious car accident when I was 14 by just a few days. Left me in hospital for ~half a year, pretty serious aftereffects as well. That was a horrible thing to happen health-wise, but I think I've come out of it all the more wiser so I suppose it depends how you'd define the 'worst' day ever.1