Scariest: Crossing from Jordan into Israel back in 1976.
Longest: Crossing from Ukraine into Poland. If I didn't pay a man to pay another man to help expedite the process I might still be there waiting there.
Stupidest Question: Crossing from Poland into Lithuania, the border guard asked me how many "chassies" my car had. I atill don't don't even know what a chassie is. I went into the glove box and handed him the pack of manuals for the car.
I was studying in Israel during College, and went on a day trip to Sinai to go diving on my birthday. I crossed the border without a problem, hectic as it was. The boat docked back closeto the last time that you could cross back into Israel. I handed my passport to the Russian emigre and she studied it for a while. I am used to having people take second looks, because I have long dark curly hair in the photo, but at the time it was buzzed and dyed blond. She calls a friend over to look, all the time speaking in Russian. I am beginning to think I will be spending the night in Egypt. Finally, they count to three in Hebrew and started singing Happy Birthday. Its fun crossing the border on your birthday!