Coral Gables High School, Florida, 1986. (Photo: Erica Berger/Miami Herald)
This stylish gentleman is asking a question of Vice President George Bush during the latter’s visit to the former’s high school. That night, filled with newfound confidence, he (the stylish gentleman, not the VP) surprised Molly Ringwald at the prom.
(Photo via the Boston Archive/eBay)
2 Warps to Neptune 
I thought you were doing something on the Duckman TV show about the Private Dick/Family Man and his pig sidekick. This guy looks like a dumbass, so I guess there’s that.