I had one occasion where the upgrade requests went the other way.
Back when I worked for one of those big, ginourmous, international companies, I was traveling with two colleagues. We had no clue about status or perks. At the airport, we ran into a fast rising senior manager (who soon went on to become a fast rising senior partner). A bit of idle chit chat, and he invited us into the DL Club. We were awed and amazed that such nice places existed, and also that he would invite us in.
On boarding, he took our boarding passes and went to the gate agent and asked if we could somehow get upgraded to F with him. No room at the inn, but just the thought that he tried was a very cool thing to do.