Influenced by the what are your greatest achievements/moments as a frequent flyer I was thinking we should start a "whats the dumbest thing you've done/worst moment as frequent flyer?" I'm not sure if this is my worst, but off the top of my head it was my first mileage redemption. I had 60k US Airways DM miles and was looking at flights to Vegas that cost ~$300 from NY. I went online to check if I could book an award ticket and I found a low first one way and full economy one way (25k miles each for a total of 50k miles). I was so happy that I was able to get F one way for the same price as Y the other, but that was before I knew that 50k US Air miles could get me 1/2 of a J ticket to Europe with a stopover (at the time, one stopover each way). Somehow, I managed to call and ask if my "full" Y award was eligible for an upgrade and I was upgraded on the spot, so I guess it didn't turn out all that bad. I still regret this decision and wish I had been smarter/done my research, but I'm happy that it, along with another trip, made me question if what I was doing was the best way to go about traveling and it led me to FT (and now MP). What's yours?