1) funniest: I wore a diaper to my cousin's wedding and soaked it during their vows. As soon as they were pronounced husband and wife, and everyone started clapping, I messed my diaper.
2) strangest: I wore one to my doctor's appointment, and I wasn't thinking too hard so I wet myself on the drive there. When he had me pull down my pants so he could check my balls, he had to stick his hand down a soggy diaper.
3) scariest: I wore a diaper to Thanksgiving dinner last fall, and I was constantly worried that one of the dozens of family members present would notice something.