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Best proposal story I've ever heard hands down goes to my friend's brother:
They're Orthodox Jewish so he was studying in Israel while they were dating. She came to visit him once and he asked her how the trip was and she said "it was ok except that I hate flying alone" and he went "I promise you that the next time you fly you won't be alone." So then after they were both back in the U.S., he told her they were going on a date, in the car he went "I'm really sorry, but one of my friends is flying in from Israel today, do you mind if we go pick him up?" and started driving toward the airport then he asked if she has her passport on her. When they get there, he asked her again "do you have your passport with you?" and after she said no, he went "that's ok, it's a local flight." So he hired a plane to fly them around the city, and when they got in he went "I promised you that the next time you flew you weren't going to be alone." So as the plane was landing, he went "look out your window" and she looked outside and he had taken a giant sheet and spray painted on it "Chaya will you marry me?" so it was the first thing that she saw when she was looking out her window.
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