My absolute worst? I was given RussianPreteen.com & was very happy about it at first, since it was aged & aged domains are valuable...
...or at least I was stupid enough to believe this. I got too close to the picture to see it for what it was. I had it on adult parking (it made about 50 cents or so) and I tried selling it in an adult forum. It was only after I was royally chewed out that I stepped back and truly realized what I had. I tried dropping it, but Moniker refused to allow me to. They then auto-renewed it. I demanded a deletion after. It was, and I forfeited the renewal fee. To this day, I feel sick thinking of the domain. I donated 50 cents to charity--thus removing all profits--and learned a great lesson: NEVER GET TOO CLOSE to the picture. It'll obscure you.
Irony: the domain wasn't aged, at all it dropped, thus its time reset. Obviously, this was long ago