This happened a few years back.
I nominate the United Captain who sat next to me on my DH. He says hi and puts his bags in the overhead then proceeds to sit down. Then leans forward to take a look at my wings and asks "What's Shuttle America?" I say we're a regional airline and operates on behalf of United and Delta flying the Emb 170. He says "Oh, so when are you due to upgrade?" I tell him probably another year. He says "I don't want this to sound douchey, but I'm in the prime of my career and making great money". I told him, while cracking a smile, yeah that's pretty douchey. He laughs.
He goes on to tell me United is hiring and that I should put my resume in because they'er a great company to work for. I'm trying to exit the conversation at this point because he obviously is completely out of touch with the regional world and out of the corner of my eye I see him reaching into his blazer.
He pulls out a pair of those United Junior Pilot gold wings and a 767 baseball type card that has the aircraft info on it. Then taps me on the shoulder and says "Here you go."
At this point I am at a complete loss for words and keep quite the rest of the flight. Now I don't know if he was ****ing with me or really that clueless. To this day I get a kick out of it and picture him passing wings out to other regional guys.