Over the weekend I had to cross borders twice, first entering the USA from Canada and then going back to Canada from the USA, unfortunately my passport has not been updated for several years :c(
When crossing into the States me and my partner (she's CIS) drove to the booth and the man politely told us we had to go inside for me to get a visitors permit, at this point he takes both our passports and then tells us to go inside a building and wait for our names to be called which we do.
When our names were called we took different paths so I got to the desk first, the immigration agent then referred to me by my partners name, I corrected her and told her no, I'm (insert old name here) at which point she got that "deer in the headlights" confused look, then my partner arrived causing a second wave of confusion to wash over her, she recovered in about 5 seconds, a bit later she asked me if I was sure because my first visit to the US on my own was in '99 and that did not add up, I then pointed out I'm 35 and she wen't "Ohhh".
On the way back I handed the Canadian Immigration official our passports, he looked a bit, we had a talk about customs things and value of things I was bringing and then he said: "I don't want to be a stickler but you really need to renew your documents", I proceeded to explain to him about all the hoops I've been trying to jump through and told him I'd like nothing more than to get them updated, he then commented that this was really silly because it made their job so much harder.