1. The summer I turned 15, my boyfriend's family spent a week or so in Stowe (yes, it still exists when there's no snow), and invited me to come down for the weekend. So my boyfriend, our buddy Dean, and I hopped in the car and drove from Quebec to Vermont.
We crossed the border at one of the little tiny crossings, where I guess they just have too much time on their hands.
Now, remember, we're teenagers on a road trip. And Dean, in all seriousness, wanted to be a mortician when he grew up.* For some reason, Dean chose to pack most of his possessions for a weekend trip, stuffing it all into a rather large hockey bag.
So when the border guard asked us to take our bags out of the trunk, we collectively winced.
It took about five minutes for this guy to go through my bag and my boyfriend's. He was much more methodical with Dean's bag, in part because my boyfriend and I were dressed in shorts and t-shirts, whereas Dean was wearing black jeans and a trenchcoat with a large U2 lapel pin. At one point, he actually said "isn't a U2 a kind of Russian submarine or something?" He went through that hockey bag with some weird determination to find something incriminating - he got very excited about the Hawaian lei, for instance. Eventually, he decided there was no real reason not to let us across, so he let us pack up our bags drive off...
without ever finding the weirdly modified German hunting knife with the lead ball on the handle that Dean decided to bring along, just in case.
2. When I was in my early twenties, my biological father was working as a flight instructor in Jeddah, Saudi Arabia. After an unbelieavable amount of paperwork (including a fax that I had to bring to the corner store to have translated), I got a stamp in my passport allowing me to enter Saudi Arabia.
So that winter, I spent Christmas with my father's family in Ireland, and then the two of us flew to Jeddah. Since he was technically crew, he had to go to a separate building to clear customs - which left me on my own to go through regular customs. Alone. And female. And very obviously Western.
Naturally, one would expect a problem. In fact, it was pretty easy - I think the customs agents were afraid to look in my bags in case they found naughty lingerie or something. Their primary concern was to determine without a doubt that there was, definitely, really, absolutely a MAN on the other side of the frosted glass doors who was willing to claim me, if they let me through. Which they did, eventually, to my great relief.
2a. The return trip was the real killer - because the flight was overbooked, our flight from Jeddah to New York was diverted to Paris to refuel, which made us late into New York, where I had to change airports to get my flight to Montreal. I barely made that flight, and arrived very tired, very airplaney, and very cranky at Dorval, where the customs guy started asking me all about the declarations on my reentry card.
I wish I knew how to recreate the look I must have given him, because he immediately stopped asking questions, bade me welcome home, and sent me on my way!
*Dean did, in fact, become a mortician.