Tried to play secret santa safe, accidentally bought a super offensive gift.
I had recently joined a company of 100+ staff and signed up for secret Santa (trying to be a team player). The problem was I had absolutely no idea who the person i was given was. I asked around and all could find out was his name was Sam, he was at manager level, a family man, loved football, dad jokes and was left handed.
Ended up buying a novelty Christmas tie that lit up and put it in a novelty box that said 'left handed tie' (as all ties are sort of ambidextrous so i thought it would be cheeky and show some thought.)
I wasn't there for the gift opening, but apparently it went down REALLY badly because, unbeknown to me, Sam was missing his right hand, not only was the box in poor taste but he can't really tie a tie in the first place
Fortunately nobody knew it was from me and whoever organised the secret santa didn't tell on me, so I continued to work at the company and with Sam for another 9 years without anyone finding out. On my last day at the company i confessed and he called me 'an utter prick' bur we has a laugh about it.