I don't know if this is really a fail moment, since I couldn't do anything about it, but...
When I was at a Cities, I was playing DuskGar, with a 2-1-2 Gengar line (it was before PT, btw.), I had a Gastly on the bench, and I searched for a Gengar. (Had a candy in my hand.) I noticed BOTH my Gengars were prized. OK, I'll search for a Haunter and evolve to Gengar when I take my first prize...my ONLY Haunter was prized. >_>
This happened at a Battle Roads, I was planning on playing Amphy-Lock, but, due to circumstances, I played DuskCor instead. (Dusknoir/Gliscor, it's a fun rouge, but, that's about it. I Time Walk, and I look at prizes...I prized an entire Dusknoir line, and a Baltoy. (This was when I was only running 1-1 Claydol, due to having to borrow them.) The most annoying thing was, the Cities I had no hope of winning, as it was a horrible match-up for me. The Battle Roads I might've had a shot at winning if wasn't for the prized Dusknoir line. >_<