Many years ago, flying LGA-ORD and my boss (President of a big division of a F500 company) catches the plane at the last minute and is in the first row of Y. I politely asked (and offered to pay) to send back a bourbon to him, which the FA did for free.

Turns out he'd been to corporate and they announced his leaving the next day. He was a really good guy (and went on to run a pretty big company and did fine afterward) who got somewhat shafted so I'm glad I sent him a bourbon that day - he probably needed it.