Uncommon Gambling Stories

Okay, so you’re standing on the produce aisle and your buddy bets you ten bucks that you can’t toss a cabbage all the way over to the deli section. Since you’re generally an idiot you quickly take that bet, but little did you know that some nice old lady with the walker on wheels was bent over inspecting the pastrami. Sure, you probably gave her the scare of her life and you’re never allowed to enter that particular grocery store again, but ten bucks is worth at least fifty when you take it from a friend on a bet, isn’t it?

Truthfully, there is not a whole lot of gambling going down inside a grocery store nowadays, but that doesn’t mean that men will cease to be men. We will sometimes place wagers on the most ridiculous things imaginable and actually feel good about it after we win, even if it sets the neighbor’s cat on fire in the process. Here are two of our favorite ridiculous gambling stories that we’ve received from our readers-

The Lady in Waiting

Okay, we’ve all done this one a couple of times, but never as ridiculously funny as one of our readers. A friend bet him $100 that he wouldn’t walk up to the first random female they passed and kiss her on the lips without uttering a word (even though this crosses so many lines he could have easily ended up on the Sex Offender’s Register). He agreed, but as they walked down the street his buddy kept making sly comments and crushing his self esteem. Our reader simply couldn’t do it, but instead of admitting defeat he blamed it on his friend’s violation of unwritten man laws and demanded a do-over. They finally altered the terms a little so that the buddy would stay in the car and watch with binoculars.

Well, they pull up to a convenience store to see a quite attractive female standing at a payphone. Our reader gets out, goes straight up to her and leans in, and the next thing you know the entire area is swarming with police. It turns out that the female was an undercover cop posing as a prostitute…but that’s not the worst of it. The buddy didn’t happen to have binoculars with him at the time so he was viewing the gal through his hunting rifle scope…they both barely avoided jail time over that one.

The Chug

Another one of our readers was out on the town with some friends and they decided to gang up on one of the non-drinkers. This guy wasn’t the designated driver or anything so everyone else felt like he was wasting the night by not having a few beers…but he insisted that he simply did not care for alcohol. Well, as the night wore on, the taunting and insults kept getting worse, so finally the sober friend posed a friendly wager with the rest of the group. He bet everyone there that he could chug more beers in the next five minutes than the rest of them combined; so everyone quickly shelled out $20 to make it happen.

Well, the sober guy went straight to the bar, chatted with the bartender, and casually walked back to the table with two beers in hand. They were ready to start the bet but the sober fellow insisted that his friends start with full beers, and out of good spirit he even handed them a twenty out of his wallet. Since they were on the clock, all three guys rushed to the bar and ordered a beer each…but the bartender refused to serve them. It turned out that the sober friend told the bartender that all of his friends had fake ID’s and a police officer was about to arrest them, so the argument lasted just long enough for him to finish two beers and collect the money.

We also have a lot of stories from readers who managed to win something from Leicester City’s EPL victory in 2015/2016. But quite frankly, we’re too envious of them to report them. We told them it was old news. Not interesting enough. But what we were actually thinking was, “Lucky bastards”.

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