Not my tale and I don't tell it as well as my mom does, but the Germany thing reminded me
When my mom was in high school, her family (my grandparents, mom, and uncle who was ~8 at the time) went to Europe for - I don't know what you call it, but it's when a pastor swaps churches with another pastor for a month or more. Anyway, as part of this, they did some touring around, including East Germany. Mom remembers it as being one of the scarier aspects of the trip, because of the intense security involved in getting into the country.
I should mention that my uncle has always been a huge nerd since before being a nerd was cool, and he looks (and has always looked) it. At the time, he had giant glasses, buck teeth, and wispy white-blond hair that stuck up in all directions - about as stereotypically dorky as you could get at the time
So they get to the wall and they hand over their passports and exchange some very, very limited German with the guards (who didn't speak English). And the guard is staring intently at the passport, scowling at mom, staring at her passport, scowling at her again, etc. Same with my grandparents. And then he gets to my uncle's picture - giant glasses, buck teeth, anti-gravity hair. And he looks at my uncle - dorky glasses, buck teeth, and crazy hair - and absolutely loses it. He calls all the other guards over, and they're all looking back and forth from the passport picture to my uncle and laughing their heads off (in German).
They were waved through, but Grandma kept my uncle's passport picture in their scrapbook of the trip as a memento. And yeah, his picture was hilarious