Oh damn, I will never forget this one:
I just finished Charles Cottles "The Hidden Reality", thought I understood everything and got cocky. I've traded futures and spreads until then and had a little experience with derivatives math.
In the beginning of SEP 2009 I loaded the boat with call front spreads on GLD when it traded around 98$. Skew was insane and I sold 4 120$ NOV calls for every NOV 100$ call I bought. I think the position was even in premium. I was betting on a GLD breakout above 100$ and didn't want to lose in case I was wrong...lol.
Breakout really happened and I was immediately down more than I anticipated. On top of that I promised my girl to go on a 4 week vacation with her starting last week of OCT. Theta did it's magic and kept the position alive, but GLD was closing in on the short strikes.
My P/L wasn't doing anything but gamma got bigger and bigger. I ended up sitting in front of my laptop in the hotel room sick to my stomach and constantly fighting with my woman.
Mid NOV I closed the position for a small loss because I just could not take it anymore. The remaining two weeks of vacation were a disaster...it rained the entire time and we were stuck in the hotel.
Back home I realized that GLD topped out at 120$ and I would have made a healthy chunk of dosh if I just kept the position...on top of that I got dumped by my girl 2 weeks later.
Good times