Geek "Tragedies" and Horror Stories

What's the worst thing(s) that ever happened in your life as a geek? Not genuine tragedy. I'm talking about something ultimately trivial (losing a prized collectible item, having your 300+ hour skyrim saves deleted, etc) that felt absolutely terrible at the time.

For me, it was playing the original Final Fantasy on NES and realizing I had used up all of my spell slots and didn't have one left to purchase the most powerful spell in the game. I was in 7th or 8th grade. I went to my room and silently cried for about 30 minutes.

There are certainly lost saved games...or never saved games, the GI Joes smashed with whiffleball bats, and the "Jazz" Transformer that I transformed one too many times... but the biggest geek tragedy has to be losing my connection with the guy I made armor with.
It was a time and money drain, but the satisfaction of seeing a bunch of sheet metal turned into a full suit of armor was well worth it. Couple that with working a Renn faire and being behind the scenes, and feeling like you (sort of) "fit in" with a crowd (in the same way Bono's drummer, whoever that is, basks in reflected glory); yeah, that would have to be my greatest geek tragedy.

I was working on this trophy that takes real skill to get and after trying hundreds of times to get it I finally pulled it off and the trophy glitches and didn't pop so I had to try it again.