I knew a Penthouse Pet when I was a regular/part of the furniture in a strip club got to know her pretty well and drove her to and from home and the airport a couple of times.

A few months after meeting her on a quiet night while having a bit of a banter with her she disputed the correct spelling of my name. I bet her a coffee date she was wrong, added a stipulation she had to wear jeans and a t-shirt not any of her usual wardrobe.

I won, we had coffee a couple of days later, she turned up in denim shorts so cut off she was risking being done for indecent exposure and a t-shirt that looked like it was purchased from the kids section.

I spent our “date” getting the expected looks from every other guy in the cafe wondering how the ugliest guy in the place was with the girl who looked (and dressed) like a pornstar. Was fun. Glad I don’t move in those circles anymore.

Still kinda entertaining to me that I was at the strip club 2-3 nights a week for a good 7 months when I was unemployed and had no money, use to pick up odd jobs for the bar and get dancers rates on my drinks cause I was friends with the management. Once I was working and had money I pretty much stopped going entirely.

When I was in about 8th grade, I had a history teacher bet me a case of pop that he could prove 1+1 did not equal 2. I said okay, and he told me to come in tomorrow and he’d have the proof on the board.

He was also our football coach and taught several grades. I went to a small k12 in the country. He was generally liked by the students but didn’t much like smart kids so he was a real smug prick about it.

That evening I mentioned it to my dad. He smirked and told me he knew exactly what was about to happen. Bear in mind this was pre broadband and I wasn’t going to crawl gopher at 9600 to find it, so it was good my dad is a nerdy engineer.

Next day; knowing he’d have a divide by zero issue somewhere in a sea of math salad, I walked into his class. It wasn’t my class but the first of the day. Kids a few years older, looking at me askance and laughing as he smugly said nothing but pointed me to the board, where there was predictably a math salad, tons of variables and algebra.

I think he expected me to crunch for a while… really chew on it, so he went right back to lecture. About 10 seconds later, I saw it, and just turned and looked at him, waiting patiently. He didn’t see me, but the class changed. A small din rose and the older kids started smirking and whispering.

He had such a shitty look when he turned to me, “I’ll take Diet,” he said.

“Really?” … “You can’t divide by zero.”

“I didn’t.”

“Right here, coach. x-y here is zero in the denominator. Better luck next time. I’ll take Cherry Coke.“ And I walked out, like a movie arsonist walking away from the fire. In my head, I was screaming. My heart beat like I’d run up a mountain.

Only silence was left in my wake that day. I was, for one day, the coolest bloke in town. I didn’t get the girl or anything, but there was Cherry Coke for the class the next day when I arrived.

My family was making bets on when a grandchild was going to be born. I bet he would be a week late to coincide with his parents anniversary. I was right.

2 cousins and me participanted in a Formula 1 Fantasy league over the whole season (24 races, all year long). We bet some money on it.

I created a program that would run simulations, scenarios and see tendencies that helped me make informed choices before the next race. Aditionally, one of my cousins was very annoying about it, he would use every small victory of his team to agressively mock us in our faces, and this made impossible to talk with him about actual F1, because all he could see was this fantasy league.

Each of us had right to manage 3 teams, and we agreed that winner takes 75% of bet pool, and second team takes 25%. In the end, I won it all :)

It was satisfying to 1. win thanks to a program I created; 2. win to my annoying cousin, 3. win both first and seconds place.