Worst bet ever was actually a competition on whi could drink more. But worse it was not alcohol or anything like that. Its was Balsamic Vinaigrette. Both of us ended up going through the entire bottle taking turns. Evidently I puked first due to not eating prior so all the oil kinda was just sitting in my stomach.
The easiest bet ever for me was when some of my south of England friends came up to Scotland for my 21st a few years ago and we had a drinking competition they didn't believe that I was a stereotypical scot who can drink them literally under the table I carried them home that night ?