Six weeks ago, I told you about a $100,000 prop bet between two poker players, Rich Alati and Rory Young. To win, Alati would have to spend 30 days alone in a pitch-black bathroom, with occasional food deliveries, but no electronics. His only luxuries were a yoga mat and a massage ball.

Here’s the update: when it got to the 15-day mark, Young started getting worried he’d lose the bet, so he offered to buy out for 50%, but Alati said no, despite suffering hallucinations and depression. Each day after that, Young upped the offer until, on day twenty, Alati agreed to accept $62,500.

That’s the craziest bet I’ve heard of between poker players, but far from the only one. Brian Zembic became famous in the mid-90s when he won $100,000 by getting 36D breast implants and keeping them for a year. Not only did he get paid, but he kept the breasts (and still had them as of a few years ago). Gambling writer Michael Konik told Zembic’s story (and many others) in a book appropriately titled, “The Man With The $100,000 Breasts.”

Bets between poker players, usually done to break up the boredom of a long session, can be as simple as whether the flop will have more red or black cards, or which team will cover the point spread in some random college basketball game neither cares about but can see on the nearest TV.

But I’ve also bet a friend how long it would take before a certain known-to-be-bad dealer would pitch at least one of the cards to the wrong player as he went around the table (he set the over/under at 4 hands, I took the under and won when it happened on the very first!). I’ve been involved in wagers over how many water bottles someone could throw across the room into a trash can (he hit nine out of ten and I lost), as well as how long it would take for one guy to drink three 10-ounce bottles of water (less than 24 seconds, if you’re wondering).

Just a couple of weeks ago, I was at the table when Ron and Ross bet on how long it would take my friend Andy to finish that day’s Wall Street Journal crossword puzzle. Ross set the over/under at 34 minutes, which I knew was way too high, considering that Andy does these things every day. Also, this was early in the week, when the puzzles are less difficult. I’m nowhere near as good as Andy, but I did that day’s NY Times crossword in less than a half-hour. Ron smartly took the under and easily won the bet when Andy whipped through the clues in just 12 minutes.

Several years ago, a basketball hustler named Clint came through town, sat down in our hold ’em game, and started bragging about his talent for shooting three-pointers. He was willing to bet anyone that, out of 50 attempts, he could hit 37 or 38, even if he had to get his own rebounds. That started some of the players talking, but I stayed silent. One thing I know about hustlers is they always start way below their actual range, so I figured Clint’s true accuracy rate was well above 90%. To make a long story short, he hooked one guy into a bet for five thousand dollars if Clint drained 40 baskets, and they left to go to a gym that was open around the clock. The next day, I heard that Clint had clanged the first two off the rim, then offered to double the bet — which the sucker accepted — before making 47 of the next 48, or 96%!

Then there’s the one I heard about in Vegas years ago. I don’t know anyone involved (or if it’s even true), but it’s a great story.

It involved a guy (let’s call him Bob) who was talking about being a top ten tennis player in college but never turning pro. He was regaling the table with tales of his successes, when one of the other players (let’s call him Jim), who had been very quiet, offered up a wager for a thousand dollars. Jim said he’d meet Bob on the court for one set of tennis. Next, Jim said he’d give Bob a huge advantage — five games and a 0-40 score in the sixth game. Despite that disadvantage, Jim said that from then on, Bob would never be able to hit a winner before the set was over. Bob thought about this, asking Jim several times to repeat the conditions. Satisfied that he’d only have to score a single point, Bob agreed.

The next day, they met on an outdoor court, surrounded by everyone else who had been at the poker table and lots of others who had heard about the wager by word of mouth. Before they started, they each handed a thousand dollars to a third party they both trusted. Then they went out onto the court, where Jim promptly served the ball into the net. That meant he lost the point, and the set. But, he pointed out, Bob had not returned it, so Jim won the bet. Realizing he’d been conned, Bob laughed and told the third party to give the cash to Jim, who accepted it with a huge smile.