10 Silly Stories About Gambling

Casino Neon Sign, Slot Machines Inside Casino
Gambling is serious business. It’s a serious hobby with serious money on the line and, as such, is only fit for serious people. Right?

C’mon! Who am I kidding? While I would never argue that real money gambling isn’t serious or that being good at it doesn’t take work, that doesn’t mean you have to get all serious when you do it. Gambling should make you smile as often (or more) than it makes you money. Heck, if you collect more funny stories than big pots, at the end of the day, you’re still going to come out a winner.

In fact, as you’re sitting there reading these stories, I bet you have a pretty good tale about gambling yourself. If so, feel free to reach out and let me know. It might even be worth a second article of some of the best silly tales. In the meantime, though, here are 10 stories from the world of gambling we found a little unique, a little fun, and a just a bit silly.

1 – “That Is a Bad Beat”

A friend of mine knows a guy who runs a bar. A lot of the folks who frequent this bar tend to play cards and, like good card players do, talk a lot about playing cards. However, in the world of poker playing anecdotes, there’s always a danger that someone is going to start talking about their bad beats.

A bad beat is when a player wins even though the odds are against that person winning.

Pretty much any time you draw to an inside straight or two pair magically becomes a full house on the run in Texas Holdem, that’s a bad beat.

Anyway, sometimes bad beat stories are fun. Sometimes, they just turn into a player’s excuse to whine.

Because of this, at this guy’s bar in Philly, there’s a special tip jar set aside just for those who would grouse about their bad beats. Whenever anyone starts to tell their favorite bad beat story, the bartender points at the tip jar and waits for money to be deposited. Only then does the bartender listen (well, partially listen anyway) until after the story ends.

Then, he looks at the teller, says “That IS a bad beat” and goes on about his day. This just goes to show that even when you pay, no one is interested in your bad beat story.

2 – He Got so Angry Over Pocket Kings

I had an old boss who really got into online poker. This was back in 2003, when online poker was getting popular and you could still win some good money at it.

Anyway, he was working on a project that required him to sit and watch data get loaded into a system. He didn’t have anything to do while the data loaded, so he worked from home and played a lot of video poker. Plus, on the days he did come to the office, all he did was talk about his bad beats.

Because he was my boss, I was unable to collect tips.

Casino Poker Chips, Deck of Cards, Pocket Kings

Anyway, one Saturday, about 10 of us (including my boss) got together to play poker. From the beginning, he was clearly better than all of us. Fortunately, he just kept getting really crappy cards until at some point, he gets pocket kings. I don’t know this at the time, but I do know that I get ace/king off-suit and proceed to bet aggressively.

At some point, my boss folds because he thinks I have pocket aces when in fact, I end up winning the hand with ace high. The problem was, he was expecting us to act like players who knew what was going on. Because we weren’t, we kept unintentionally bluffing. Once he realized this, he started stomping around the house we were in, screaming that he should have stayed in the game.

Pretty quickly, he ran out of chips and sat at the end of the table reading Maxim magazine for the rest of the night because he was too angry to buy back in.

3 – The Gambler’s Fallacy Doesn’t Work Except When It Does

I had another boss who swore he could pick a slot machine that was about to pay off big. Being a facts and stats kind of guy, I generally find such claims to be highly dubious and figured his string of three straight nights coming back from the casino with more money than he started with was just luck.

Anyway, one day he convinced me to go with him so he could show off his superpowers. I went along figuring that I would be front and center for his luck to run out, thereby proving me right and setting everything right with the world.

Except he won. He was literally playing three slot machines at once when he pointed to a machine, gave me some coins and told me to go do a max play. Within three spins, I’ll be darned if the machine didn’t pay out.

He ended the night up 20 bucks. I end up losing about the same, but gaining a deep and abiding sense of confusion about how, exactly, he knew that machine was about to pay off.

4 – Jumping in on Hot Dice

A friend of mine’s dad likes to play craps and kept telling my friend to “play the hot hand” (make risky bets when a roller gets lucky). My friend just kept playing the pass line and pocketing his chip every time he won.

Casino Craps Table Layout, Two Red Casino Dice

At the end of the night, my friend’s father ended up losing his budget for the night and my friend took his $60 and bought us dinner.

5 – I Wanted to Quit, But I Had Three Hours to Kill

My wife once won some money at a slot machine in Kansas City within the first few minutes of being there. When I asked what happened to it, she said she lost it all. “I knew I was going to be there three more hours and I didn’t want to sit and do nothing.”

Casinos always find a way to get their money back!

6 – It’s Not a Gift Card

The first time my friend went to visit Las Vegas (which was her first time playing blackjack), the dealer gave her a card to cut the deck. Not knowing any better, she tried to pocket the card thinking it was a free gift.

7 – Beware the Friends List

Back in the days of Full Tilt Poker’s friends list, one of my friends got chewed out by a guy to whom he just delivered a bad beat. To get back at the guy, my friend added the guy to his friends list and spent the next two weeks finding him online, playing against him, and telling the table this dude had taught my friend to play poker.

After two weeks, the guy finally lost it and started yelling at him in the chatroom. Revenge achieved!

8 – I Think He Missed the Point

One of my friends met an older gentleman in a poker room. After a while, the older man asked my friend if he played golf. My friend said he did not. The old man said he used to, but later found out that bowling had air conditioning.

Poker Room

Later, the same guy asked if my friend went to the doctor because he, the older man, never did. His brother did, the older player said, at the age of 72 and died. The old man, at the age of 76, swore never to go to the doctor because that, after all, is what kills you.

9 – The Lobster

The Lobster falls under my friend’s list of great poker nicknames and sayings. “DBSRO,” the Lobster told my friend.

“Don’t be so results oriented.”

It was good advice. So good that the Lobster was hired to do some work for my friend who paid him ahead of time for additional work. Unfortunately, the Lobster was not results-oriented enough to actually do work he was hired to do.

10 – Doctor Kill

Another great poker nickname, “Doctor Kill”.

This guy would show up at the poker room in his scrubs around eight, play all night, go to work, go to bed around four, and come back for more.

Unfortunately, the man was always angry and one of the worst players my friend had ever seen. Hopefully, that was the only reason he got the nickname “Doctor Kill.”


As you can see, funny poker stories can come from different angles, different games, and different venues.  The stories can be funny, be about revenue, or focus in on the unusual conversations had around the table.

Hopefully, these stories were amusing to you and made you want to get out there and experience all of the unique players you might find at your local poker room or casino.