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Classic setups include someone coming out of the closet or the resolution of a Will They or Won't They?. Classic subversions include compromising situations that imply one of the above or the losing character immediately winning the money back due to a second revelation.
- Empowered: Ninjette and Caged Demonwolf make a side bet on how long Emp and ThugBoy will be apart after a fight. Demonwolf wins a set of The Wire DVDs
- At the end of Strange Powers after England and America hook up after a good deal of UST, Romano pulls out a binder and talks about some money he has to collect.
- Sinbad: Legend of the Seven Seas included among Sinbad's crew two men who passed money back and forth throughout the movie. The bets were on whether or not the earth is flat and whether or not Sinbad would survive his latest escapade.
- In Die Hard, when Hans is interrogating Takagi, who refuses to give up information, Theo says "I told you" and Karl replies "It's not over yet." After Hans kills Takagi, Karl hands Theo a bill.
- At the end of Down Periscope, there's not just a yell from the chronic gambler to "Pay Up" on the misfit's boat, but after an admiral who hated the protagonist took over the opposing boat a surreptitious exchange of a wad between the captain and first mate.
- The first Lipstick Lesbian close encounter in D.E.B.S. is followed by the villain's sidekick telling the heroine's friend "You owe me fifty bucks."
- The Avengers: Nick Fury offers to bet Steve Rogers $10 that there's still surprises left in the world for Steve. We don't see Steve accept, but after the Helicarrier takes off Steve walks onto the bridge and hands Fury a ten dollar bill.
- Fred and George Weasley in Harry Potter and the Order of the Phoenix bet on a Hermione vs. Ron duel.
- Moreso in Goblet of Fire, when the twins make a winning long-shot bet on the outcome of the Quidditch World Cup. And spend the entire rest of the book trying to collect their windfall, because they were paid in leprechaun gold, which vanishes in a few hours.
- In The Truth, Vimes assumes that someone in the Watch will be running a book on whether William De Worde will survive. "Find out who's responsible, and once you've found out it's Nobby, take it away from him."
- Nobby also runs a book on Moist von Lipwig's chances in Making Money. Such is the Lipwig mystique, however, that even though he thinks he's doomed, no-one will bet on that.
- Done in the Honorverse novel 'At All Costs' between Queen Elizabeth and Hamish Alexander as to whether Honor would realise that she was about to become Unconquered's new CO.
- The Wraiths make a lot of such bets. After Wedge learns that Wes set one up speculation about what he would do when he realized the flaw in a plan which involved working closely with Chewbacca when he himself didn't speak Wookiee, he decides to take his most serious revenge on Wes.
- Later books in the Stephanie Plum series make reference to Rangeman employees having a pool going on how long any car Stephanie gets from Ranger will survive.
- Hendricks in Dresden Files has one with Miss Gard at one point. It's on if Murphy will figure out a spy. She did. Hendricks won.
Live Action Television
- On an episode of CSI, Greg Sanders's replacement eventually cracks from the pressure to be just like Greg and quits. Nick forks over a bill to Warrick, who really shouldn't have been participating since he had a gambling addiction in the first season.
- There's also been a whole episode with a Running Gag about Nick and Warrick having a bet about what happened to the Vic of the Week, so it seems that Warrick can engage in "fun" bets with a buddy without a problem.
- Another CSI sees Catherine and Grissom making a bet over whether two murder victims' deaths were related or not. At the end it turns out they were both right, and Cathrine rips a bill apart and hands half of it to Gil after the very heavy conversation, this is a tension breaker when Grissom reminds her that doing that is a federal offense.
- On Scrubs, when an exasperated Dr. Elliot tells Dr. Kelso that she came out of the (fake) closet to her mother, he deadpans, "Well, it seems the boys in Radiology owe me quite a lot of money."
- When Ellen comes out of the closet, her friends ask her if she's sure about it, and, when she says yes, Joe pays Audrey, who then pays Ellen's cousin.
- In Tales of the Gold Monkey, Jake gets in a fight with a visitor and the following exchange ensues.
Sarah: (to Louie) Do something!
Louie: (to Gushie) Forty francs on Jake.
- It is a common occurrence during the show's many other bar brawls, too.
- House sets up bets with his underlings, friend and boss all the time, and some of them have picked up the habit from him. This is not the classic form of the trope, however, as that generally involves the audience not knowing a bet was in progress until money changes hands.
- In a season 4 episode, House's ducklings were making bets with Chase on which of them would be fired. At the end of the episode, even though they all screwed up one way or another, House doesn't fire any of them, meaning that Chase won all the money. Foreman then confronts House, saying that he can't believe he would do something that 'nice' without financial gain. Sure enough, it is revealed that House and Chase cut a 50/50 deal.
- Father Mulcahy from MASH does this virtually every time the subject comes up.
- Happens several times on Friends. Once, Joey was deliberating on whether to sleep with a casting director for a part. He comes in and tells the others that he refused, only to be offered a bigger part. Ross and Chandler pay Rachel and Phoebe. Then Joey implies that he did sleep with her for the better part. Rachel and Phoebe hand the money back.
- NCIS once featured Ziva, Gibbs and McGee having a bet over what interrogation method Tony would use.
- Another one had Abby, wearing a cute hat she'd cut from a clean room uniform, present a similar hat to Kate, and ask her to try it on. She does--and McGee gives Abby twenty bucks. He leaves, despondent...and Abby gives Kate her ten-buck cut.
- In an episode just before the one where McGee and Abby made a bet, there was a bet between Tony and McGee where Tony had to get Kate to admit she was Tony's wife.
- One episode of Frasier saw Lilith's husband leave her...
Frasier: ...and get this - for a man.
Niles: Damn - I owe Dad $5!
- Several instances on Myth Busters, either from Adam and Jamie or the Build Team, on the outcome of an experiment. In one Build Team wager, a cameraman was drafted to hold the money until the bet was resolved.
- On a first-season episode of Extreme Makeover: Home Edition, there was a bet between the four designers over which pair (the men or the women) could make a nicer room, with the losing team cooking dinner for the winners. The competition heated up to ridiculous extremes, to the point where they were even trying to sabotage each other. Ty called off the bet, bought everyone pizza, and (off camera) told them to never do that again.
- An entire episode of The Office revolves around this, as bets are placed on the characters' quirks. Such as: Whether or not Creed will notice if his apple is replaced with a moldy potato, or Whether Kelly will mention five Romantic Comedies in a speech about Netflix.
- In The Big Bang Theory, Sheldon once ends up offering "his spot" on the couch to Howard in an attempt to apologize to him. While Howard is describing the advantages of the spot, Sheldon cracks and tells he wants his spot back.
Penny: "How long?"
Leonard: "Ninety-four seconds." [reaches for money]
- When Alan's marriage to Dumb Blonde Kandy fails in Two and A Half Men, everyone seems saddened... because they picked the wrong month in their betting pool for when they'd break up. Everyone, that is, except for Judith, his previous ex-wife, who won the pool.
- During the second season of Food Network's Worst Cooks in America, chefs Anne Burrell and Robert Irvine had a side bet about whose team would win. If Anne won, Robert had to bleach his hair blonde. If Robert won, Anne Burrell had to lose her trademark hair and get a make-under. Burrell won, and the photo evidence is here.
- Married... with Children: Marcy once showed up at Al's with a boyfriend (the episode was from after Steve left and before Jefferson's debut) and had him ask Al what his job was. Once Al confirmed being a shoe salesman, the boyfriend gave Marcy some money. When Al told how long he kept the job, Marcy's boyfriend gave her more money.
- In Cyrano De Bergerac, Cyrano has threatened punish Montfleaury if he acts in “La Clorise”. Raguenau and the first Marquis bet a fowl “a la Raguenau” about if he will fulfill his threat.
First Marquis (shrugging his shoulders) : He will not come!
Raguenau: I say he will! and I wager a fowl—a la Ragueneau.
The Marquis (laughing) : Good!
- In Jedi Outcast when Kyle decides to keep his lightsaber, we are informed that Lando owes Jan five credits.
- In Dragon Age one of the side conversations between companion characters Morrigan and Zevran (the side bet being between Zevran and a third party member)
Zevran: They are goddesses receiving their subjects, just as you should be. Whatever would be annoying about that?
Morrigan: I have no wish to be placed upon a pedestal.
Zevran: But you deserve no less. You should be admired by painters, copied by sculptors, exalted by poets! Surely you know that yours is a beauty so exotic it-it would turn the eye of the Maker Himself!
Morrigan: Well, I suppose I...
Alistair: By the Maker! You were right! You win.
Zevran: I think you owe me five silvers, yes?
Morrigan: I hate you all.
- Emi and Rin of Katawa Shoujo repeatedly make bets on whether Hisao will keep his word and show up to events. Rin tends to lose, since she's the one betting that he won't show up.
- Kenji also loses a 1000 Yen bet over Lilly's ethnicity.
- Ace's mother in the webcomic Too Much Information is a repeat offender.
- This strip from the webcomic Narbonic.
- Seen here in the webcomic Get Medieval.
- Betting on who the new mayor is in this Dominic Deegan comic.
- Here in Knowledge is Power, with the twist that the character in question is wrong about winning the bet. (The bet was on whether Emjay's supposed boyfriend David really existed; the "David" her friend just met was actually an alien shapeshifter who happened to be using the name.)
- This strip from Order of the Stick.
- This has been used twice in Wapsi Square. The first time, Shelly made a bet with Bud that Monica wouldn't be able to figure out how she protected herself from being shot. The second time, Bud bet Brandi that Monica wouldn't be able to keep her hands off of a supernatural artifact.
- When Butters in South Park tells his parents he has a girlfriend, they exchange money according to their bet on his sexuality.
- And of course, the entire subplot about the Kyle sucking Cartman's balls in "Imaginationland."
- Johnny Bravo was subject to this trope once. His sensei was arguing with a rival martial atrs teacher. When Master Hamas (Johnny's sensei) said even his worst student would defeat his rival's best, the rival picked Johnny. After the fight, it was revealed Hamas was so sure Johnny would lose, which he didn't, he made a side bet against his student. Instead of promoting Johnny to a higher belt for winning the fight like Johnny hoped, Master Hamas punished Johnny.