I'll bet on anything.
I love to bet 100 dollars with friends on tons of funny stuff, unfortunatly most of my friends don't have the same desire so they just own me. I've won and lost some hilarious props over the years and some we're just amazing to witness.
Last weekend I got generally crushed on props, and it got started right away when inyaface, eagles and I were in a cab quite late to get to the airport. We were on hold with the airline while racing along the highway in a snowstorm. I proposed the bet of "will we get there or will the airline pick up first" I wanted to take them answering side and when nobody would take that I took the other side just for the action... of course the dude picks up right before we get there.
At one bar while we were out we all ordered these ridiculous 25 dollar giant drinks that look like something you should only drink with a girl poolside in the dominican and of course I issued an open hundo chug challenge to the table. Inyaface took me up on the offer and I jumped out to a decent lead before succumbing to brainfreeze.
The night before that while out drinking with Gavin Smith, Bill Edler, Kelly Kellsner (The tournament organizer) and a few others we were playing some game where everyone puts 0-3 coins in there hand and you take turns guessing how many coins everyone holds as a group, whoever is the farthest off gets eliminated until one person takes down all the money. In one round I got heads up, and I had the 'button' meaning I got to guess last... HOW COULD I LOSE? I put three coins in my hand giving myself plenty of chance to win. Somehow the old man I was up against insta says 3 and opens his hand proudly displaying 0 coins!! How did I get owned so bad?!?!? Well he was kind enough to let me know as he was raking in my money that as I was drunkingly waving my other hand around gesturing as I was talking about something he saw I didnt have any coins in my hand so they all must be in my clenched fist...

what a fish
I couldnt even win the neutral EV gambles, I lost a few hundo betting vs Snoop Todd and some others where we would pick 'horses' to win low stakes SNGs on Poker Stars and then cheer them on. let me just say if you are a three dollar sit 'n' go player, dont ever let me cheer for, you will come last every time.
By far the biggest ownage of the weekend was served by the hands of Bill Edler. He was talking about how the night previous him and some others at dinner were taking turns setting over under on celebritys ages and betting them for a hundo a pop. He said he made a killing on Avril Lavigne. I told him I was pretty sure I knew how old she was and someone else said 25. He said look, Ill let you take either side you want for a hundo I know she's not 25. I paused and thought about it, I had just made it clear I thought she was younger and he still offers me the bet? Now I dont know what to think... I go over to 'out-smart' him... sigh/lifetilt (she's 23).
Its funny how much money you'll pay to find out something you thought you knew but really didn't. I paid a thousand dollars just to find out I couldnt do one thousand push ups in 24 hours once, pretty sick right? Then again I paid a share of 5k once to find out how awesome it would be to see someone jump into a tank full of sharks and that was worth every penny.
"Sometimes you eat the bar, and sometimes, well, he eats you."
-Peter
Also I was just reminded of another prop I have lost recently to my good friend chuddo. We bet 100 bucks on a pro dwarf vs teachers basketball game where he set the line at -4.5 "giants". If you dont know what Im talking about ask away here and Ill explain further. Anyways, I gave him the points and picked the giants and of course somehow the giants win in double OT BY ONLY 4!!!! The really funny thing is he also bet durrr a 100 on the over under and he picked over. I told chud he was a huge dog to scoop and would offer him 3 to 1 which he didnt take citing 'I already have enough action on a dwarf basketball game I cant even sweat'
Sometimes my friends save me money like that.