I've been reminiscing a lot today, and got to thinking about this. Things that were really cringy and awful at the time but make me laugh now and I bet we all have plenty stories like this.
One memory pops up of a man who I dated for a couple of weeks that spent large amounts of time moaning about his myriad health problems and announced "well, you're really fat but I'll think about sleeping with you because you're quite pretty".
Strangely enough, I declined his thoughtful offer. He was most put out.
I'm trying to think of some more but my mind's gone blank...