I've had some fun ones... flying into Montreal for a weekend in a January... why am I coming to Montreal in the winter? Well, it's 45 and sunny out and it's dirt cheap and no tourists around. They then started asking me about what I did, found out I worked for an airline, then were baffled I was flying on an airline I didn't work for (because the ticket on Delta was $100 one way and that's better than playing standby). Round and round for like ten minutes. Similar with UA into YYZ on another occasion going to a conference for work. I told them all things considered, I did not want to be there and found the whole trip inconvenient so if they wanted to send me back that gave me valid excuse to get out of my obligations. I should know better than to get mouthy at immigration but they ceased bothering me at that point and stamped me in.

Once drove across from Watertown, NY to some observation tower because I had about 4 hours free before my flight and there isn't squat to do around there. They went through my suitcase and wanted to make sure I wasn't entering just to buy meds and duty free. I had a couple of airline safety cards in my bag that earlier on my trip a friend gave me... they were from TWA I think from the 80s so way outdated... that got some questions as to why I would be in possession of such things.

And leaving Canada was the worst... traveling Air Transat YUL to MCO. Had trouble at check-in with whatever computer system they use that interfaces with customs. It required an address of where I was staying. I gave my home address and was told that was not possible. They ended up getting someone from border control to come out and question me as to why I was giving information the computer didn't like. I said I'm a US citizen going home and I guess I could always lie if that would make them feel better and said go ahead and put in the Westin Diplomat, which was a few miles from my home, and it all worked. The border agent and Swissport supervisor walked me to security, which was odd and don't know why (Air Transat was not using pre-clear gates, immigration in MCO was a breeze as I was the only American on board).