Flying with boss
Several years ago, I was upgraded to first class on a flight from BOS to DEN on UA. I arrived at the airport and realized that my boss was also on the flight, albeit in coach. I told him that I was in first class and asked for his ticket, saying that I would try to get him upgraded too. I brought to the podium and told the agent my sad story. She promptly upgraded him. I brought the ticket back to him and said, "Sorry". He never even looked at it.
When first class was called, I got up and said, "Come on". He said that only first had been called, so I told him to look at his ticket. It was like a kid at Christmas!
Unfortunately, the flight was diverted to ORD because of weather and we had to switch planes and both of us ended up in coach for the ORD to DEN trip.