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Most I ever lost - this one occasion, I scooted through an unlocked door into a banquet room at a hotel to bang my gf under a table at a hotel downtown chicago... took my wallet and phone, set them on the windowsill overlooking the river.
We were just about done when some people came in, aparently getting ready for some luncheon next day or something. We got a little spooked and headed out real quick... I forgot my wallet.
Went down the block, laughing and having a good time, found a restaurant. Ate, the bill came - fuck! Where's my wallet... oh, hell no! I ran back to the hotel, into the banquet room, and it was all set up for the next day. My phone ended up at the front desk, wallet did not. Said wallet had almost $3000 in cash, it was all I had at the time. Since then I've never kept big amounts of cash in my wallet, I always put it in my front pocket now.
The most I ever found was a swing the other way... I was about 19 years old, broke, and in Mesa AZ. My "friend" that I was staying with just told me that although I was broke and had nowhere to go, his pregnant fiance said I had to leave. This was about 11PM, I was pissed and planning on hitchhiking to Florida to meet up with some friends... when I spied, on the ground right in front of me, a hundred dollar bill. Greyhound fare to Fort Walton Beach FL was about $80 - I grabbed some smokes, a bus ticket, and headed on out.
Good shit. :D
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