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I never have trouble with the TSA. I like to think I'm a cool, sort-of-possibly-dangerous guy, but they always let me through. I send stern e-mails to the White House, and I even googled a possible trip to Cuba, but they never have put me on any of their lists, and I always cruise right on through.
I even buy one-way tickets, but it's always just, "Have a nice flight." I am a little disappointed not to seem more dangerous.
P.S. I recommend you all check out one-way tickets. Many good deals plus ultimate flexibility. The era of the round-trip may be over.