Penny's dad would have made sure that Desmond got LOST one way or another. After the conversation in his office (the $80,000 whiskey scene) when Des wanted to marry Penny, and the scene when Pen's dad shows up IMMEDIATELY after Des is released from prison, just waiting in the car and gives him all of the letters he had sent Penelope(so penny never knew des was writing her, she must have felt abandoned). Or even that fact that he mentions the race around the world (which is long and dangerous) to him and then Des "happens" to run into a crazy lady who wants to just give him a boat to compete in this race... suspicious to me!

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