The Bet

Gambler #1: I'll never make another bet in my life!
Gambler #2: Three-to-one you do.
Gambler #1: You're on!
Gambler #2: You lose.

Some people will do just about anything for a bet, so wagers are a great excuse to have characters do just about anything. Just have someone bet them they won't. Regardless of how crazy the challenge, and how disproportionate (or nonexistent) the reward, they will go to any lengths to win. Maybe they want to show up their rival or make a point or maybe they just want to win the reward. Either way they're sure to have a whole lot of adventures trying to succeed, especially if their rival is trying to sabotage their efforts. And just maybe they'll end up learning that there are some things that are more important than winning the bet.

Examples only count when the bet is a major part of the story, if not the whole reason for the plot. So if The Hero and The Rival have a bet on who will win the sports tournament they've entered, that doesn't count because winning the tournament is the objective, the wager just adds to the rivalry. It doesn't have to be the main characters who make the bet though, they could equally be the ones being bet on, so long as the bet is the reason for the plot. May be made by the Professional Gambler or The Gambling Addict, or be part of an Absurdly High-Stakes Game. More minor examples may count as a Side Bet.

A common Romance or Romantic Comedy version of The Bet is when a character is bet that they won't/can't win over/date/sex up a certain lady. The guy will almost inevitably end up developing genuine feelings for the girl, and the girl will just as inevitably be pissed off when she finds out about the bet. This may lead to The Grovel when he asks for her forgiveness.

Compare to On One Condition, which is essentially a dead person betting their estate that you won't fulfill the conditions of the will.


  • There are a number of stories and films called The Bet which use this trope.

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    Anime & Manga 
  • In the Pokémon Special manga Ruby and Sapphire made a bet to accomplish their goals in 80 days. It ended in a draw.
    • Also, in the Emerald arc, Emerald made a bet with the Frontier Brains that he will beat them in seven days. He succeeds. Sort of.
  • This turns out to be the reason Sei Arisaka tries to steal the magical ribbon from Hime-chan, telling her he loved her and betrayal through all of that in Himechan No Ribon. The bet itself was getting a bowl of ramen if he succeeded.
  • In a Christmas Episode of Axis Powers Hetalia, Monaco agrees to go on a date with Seborga if he can beat her in poker. He loses, but she goes out with him anyway.

    Comic Books 
  • At least three of the Astérix books are based on a bet.
    • In Asterix and the Laurel Wreath, a drunken Chief Vitalstatistix bets his nouveau-riche bore of a brother-in-law that he he can serve him a stew seasoned with Caesar's Laurel Wreath; naturally it's Asterix and Obelix who are sent off to Rome to do the dirty work.
    • And in Asterix and Cleopatra, a furious Cleopatra, stung by Caesar's taunts, insists that Egypt is still a great country and bets him that she can build a palace for him in Alexandria within three months. An Egyptian architect is charged with it, Panoramix gets called to help, and Asterix and Obelix go with him. Unlike in a lot of stories, these bets are not just a pretext for a plot; they also represent the wider conflict between national pride and imperial arrogance.
    • In Asterix And The Belgians, chief Vitalstatistix bets the titular Belgians on who can destroy the most Roman camps, after Julius Caesar has stated the Belgians to be the bravest barbarians. The whole thing eventually becomes a tie, and they seek out Julius Caesar to judge. Hilarity Ensues.
  • In The Smurfs comic book story "The Gambler Smurfs", the Smurfs have Gargamel make a bet with the earl of Aubenas that he would best the earl's knights in a contest of skill so that the earl would not cut down the forest that Gargamel and the Smurfs live in, with Gargamel offering to be a jester to the earl for three years if he lost the bet.
  • Avengers Assemble #9-11 involves a bet between Tony Stark and Bruce Banner as to who can be the first to successfully rescue a missing scientist. The loser has to walk naked from Avengers Tower to the Baxter Building and back (in downtown Manhattan). In the end, they BOTH lose and end up taking the walk of shame together, Banner in his Hulk form, no less. Even better, Tony's effort to jam all electronics to prevent anyone taking pictures is defeated when Spiderman shows up to take a picture with an old-fashioned flash camera that ends up on the front page of the Daily Bugle under the headline "Naked Justice."
  • An issue of Laff-A-Lympics (Marvel) had the charity money from the day's events gambled away to a guy named Lucky Starr. The three teams confront him, and Starr issues a challenge: to locate a ceramic purple pig with clues provided to them. In a conclave of millionaires, wagers are taken as to which team will find the purple pig. Starr makes the biggest wager—on the Really Rottens. Needless to say, it doesn't end well for Starr or the Rottens.


  • "Nobody can eat fifty eggs!" Except for Cool Hand Luke.
  • Oceans 12 starts as One Last Job but the main part of the film is the wager between the team and The Night Fox.
  • In Trading Places, two brokers disagree on the "nature vs nurture" argument. They decide to bet "the usual amount" (eventually revealed to be one dollar) on what will happen if they ruin a rich man's life and let a poor man take his place.
    • When said rich man and poor man find out, they hijack the brokers' short selling scheme to take them for all they had. When confronted, the poor man said he bet the rich man they couldn't get rich and put the brokers in the poorhouse at the same time. The bet? One dollar. The expression on the brokers' faces was priceless.
  • Rat Race was essentially rich Upper Class Twits sending a odd bunch of tourists on the titular race for their own betting amusement.
    • And while waiting for the tourists to get to the destination, they bet a lot as well (on a chocolate flavor, how much will a prostitute charge for a weird service, and who will puke first while in a turbulent plane).
  • In Latter Days, gay man Christian makes a bet with his friends that he can turn Mormon missionary Aaron gay.
  • Atlantis The Lost Empire: Mr. Whitmore was a friend of Milo's grandfather Thaddeus. After an argument about the Shepherd's Journal, the following bet was made: "Thatch, if you bring me proof of that so-called journal of yours, not only will I finance the expedition, I'll kiss you full on the mouth." Whitmore remarks to Milo, "Imagine my embarrassment when he actually found the damn thing."
  • The Russian comedy Man with a Warranty (or Man with a Guarantee) starts with a wealthy businesswoman making a bet with her long-time rival that she can find herself and marry an ordinary man in 5 days or she loses everything. One of the conditions is that she must do so in one of the shopping malls she owns (of the rival's choice), and she must pretend to be a poor woman with no place of her own. Naturally, the rival isn't content to just lose. He enlists the help of the mall manager to spy on her and the security guard she's seeing. He then crashes the wedding to reveal the truth to the stunned guard. In the end, the woman is content to lose everything juts to be with the security guard, but they end up registering their marriage license 1 minute before the bet deadline.
  • The plot of Love Me If You Dare.
  • Diggstown involves an ex-convict con man making a bet with a wealthy businessman who, effectively, owns the titular town that his friend (an almost-contender back in his glory days) can beat 10 boxers one after another in 24 hours. The size of the amount constantly increases, as the con man keeps borrowing the money from a loan shark he knows with his life as collateral.
  • The Sting: Convinced that Henry Gondorf's gambling den is legit, Doyle Lonnegan ponies up $500,000 on a horse race. Lucky Dan to win at 4:1 odds. Once the race starts, Donnegan's informant says he told him to place the bet as Lucky Dan would run second. Cue the "Oh, Crap!" look on Donnegan's face.
  • Monsters University: Mike plans to prove he is scary enough to join the university's scare program by joining the Scare Games. He even makes a wager with the Scare School's dean, Dean Hardscrabble, in which, if his fraternity wins, the dean will admit every member into the scare program. The catch? If his team loses, he and Sulley are to leave the school.

  • Older Than Radio: In Mark Twain's story The Million Pound Bank Note the bet is actually between two rich brothers as to what the main character will do when given the titular bank note.
  • Around the World in 80 Days, where Fogg embarks on the trip just because other members of his club bet him it couldn't be done.
  • The Betrothed's main conflict (Renzo and Lucia's efforts to get married) is caused by a bet between Don Rodrigo and Count Attilio: the former bet he would manage to lay his hands on Lucia.
  • The basis for several Roald Dahl short stories, the most famous of which is probably "Man from the South". In this story, an old man named Carlos offers a boastful American boy his Cadillac if the boy can strike his lighter ten times in a row. The catch is that if the lighter does not light ten times in a row, Carlos will cut off the boy's left little finger. It fails on eight. Just as Carlos is about to take the boy's finger, his wife stops him - Carlos doesn't own anything; she owns all his possessions. She also has three fingers left...
  • Garren's father, a Hrum senator in the Farsala Trilogy, bets his seat in the Senate if his son can't conquer Farsala with only ten thousand troops.
  • How To Eat Fried Worms
  • Han Solo's penchant for gambling is almost a Running Gag in the Star Wars Expanded Universe, with the Millennium Falcon being the best example of that. He won it off Lando Calrissian in a sabacc game, lost it back to him in another game, won it back, and then finally lost it permanently. Luckily, Lando was trying to impress Mara Jade and gave it back.
    • That's nothing — he once won a planet in a game of sabacc, an outcome that even he conceded was pretty incredible.
  • In Heart In Hand, Darryl's spur-of-the-moment bet that he will sleep with Alex if the latter scores a "Mexican hat trick" (six goals in one game) kickstarts their relationship.

    Live Action TV 
  • Several books and TV shows are based on peoples real life experience in trying to win a crazy bet.
    • Are You Dave Gorman? : Dave bets his roomate Danny he can find 54 other Dave Gormansnote .
      • Dave and Danny have both written other books that follow a similar format (Dave Gorman's Googlewhack Adventure, Yes Man) but without the initial impetus being a bet.
    • Round Island With A Fridge : Tony Hawks tries to win a bar bet by hitchhiking round Ireland with a refrigerator.
      • Hawks followed this up with two other books/challenges: Playing The Moldovans At Tennis, Exactly What It Says on the Tin, only he played the entire Moldovan football team at tennis, and One Hit Wonderland, where he attempted to have a number one hit in any European country. He succeeded.
    • All the above, and similar personalities, are mocked on a That Mitchell and Webb Look sketch about a 'wacky guy' who makes a bet that he can make a cup of tea for everyone in Belgium.
    • The reality show My Obnoxious Fiancee was essentially a bet between the network and the lead woman. She had to maintain the lie that a paid actor was her fiancee until the wedding, and convince her family to attend, while he acted like a boorish loser for several days leading up to it.
  • This is the entire premise of the show Kenny vs. Spenny.
  • The Adventures of Superman: The Hostage Situation of "The Human Bomb" was set off by Bet-a-Million Butler making a gamble with another man that he could control Superman for thirty minutes. Of course, he lost
  • Rebelde Way. Pablo Bustamante. Again, and again, and again...
  • Subverted in Scrubs. Dr. Cox and Turk have a bet, Cox betting that Turk is going to kill his patient, and Turk betting the opposite. The Patient makes a full recovery, Turk does a victory dance, holds out his hand for the money, and Dr. Cox calmly points out that he just wagered 20 dollars on a human being's life. Cue Heroic BSOD (despite betting on his skill as a surgeon SAVING the man's life).
    • Another episode of Scrubs had the Janitor bet JD he couldn't learn the names of everyone in the hospital. The stakes are that if the Janitor wins, JD has to do his job for a week; if JD wins, the Janitor will do his own job for a week. JD questions this, until the Janitor explains he means he'll actually do his job for a week. The Janitor wins the bet of course, by exploiting his own status as The Nameless
  • Seinfeld and the episode The Contest, a bet of who can remain Master of their domain the longest.
  • A recurring element of Barney's character on How I Met Your Mother is that he is a gambling addict. This comes in two flavors. Him readily and willingly betting any amount on anything, or - more appropriate to this trope - going on wacky hijinks because somebody said something (normally seducing a woman) couldn't be done in some bizarre situation.
  • One Drake & Josh episode titled "The Bet" had Drake and Josh betting they could quit their bad habits longer than the other. In this case, Drake's addiction to junk food and Josh's addiction to video games. The episode also has their parents making a bet on which boy would cave in first. Audrey betting Josh would win, and Walter betting Drake would win.
    • In another episode Drake and Josh bet who can get more dates in a week. Drake ends up falling in love with the first girl he meets.
  • In Kenan & Kel, Kenan bets Kel that he can't go a week without drinking orange soda. Anyone who watches the show knows how much Kel loves orange soda.
  • In Friends, Ross bets Chandler $50 that he can't go a week without cracking a joke. Of course, during the next days everybody does their best to screw Chandler by putting him in situations in which he would normally make jokes. In the end, Chandler ends up giving Ross $50 and tells all the jokes he would have said during the whole chapter.
    • In another episode, Chandler and Joey make a bet with Monica and Rachel that the guys know more about the girls than the girls about the guys. Monica (in her usual ultra-competitive self) raises the bet: if the girls win, the guys must get rid of the chick and the duck, but if the guys win, they have to exchange apartments. In the end, when neither Monica nor Rachel are able to remember what Chandler's job is, they lose.
  • An episode of Barney Miller had a bet between Yemana (to stop gambling) and Harris (to stop smoking) to see who could last the longest. At the end of the episode, when the couple from the main plotline settled their differences, there was this exchange:
    Yemana: You know, I think they'll make it.
    Harris: Aw, I bet they don't.
    Yemana: You're on!
    Harris: You lose. (lights up)
  • CSI 'Hitting The Cycle' centered on a betting pool regarding who would be the first to have a natural, accidental,homicide and suicide all in one night. Superdave, the coroner's assistant, won, though only because the other assistant died of natural causes during his shift.
  • The subplot of CSI NY 'Nine Thirteen' has the team trying to figure out whether or not Lindsay is pregnant. It's only made fully clear at the end, but they're trying the whole ep to get her to talk. When she admits to Danny that she is, they are all shown paying up on the bets.
  • In the second episode of How To Rock, the members of Gravity 5 challenge each other to give up their signature habits. (Texting for Casey, insulting people for Stevie, checking his reflection for Zander, and a fictional version of Angry Birds for Kevin and Nelson.) Predictably, they all spend the entire episode trying to tempt each other into indulging their respective habits.
  • The show Ed had this with Mike and Ed constantly betting each other $10 to do random stupid acts. This includes having to make an order at a diner in rhyme and only being allowed to say burger me to order.
  • The Aquabats! Super Show! episode "Cobraman!" is filled with a lot of these. The MC Bat Commander's tendency to accept these bets, despite his losing history with them, is used against him in a battle against the Cobraman for the Battletram.
  • Subverted in Elementary. Sherlock Holmes (not shown to have any particular skill at basketball) bets a suspect he can make a basket from a very long distance, and the suspect agrees to be interrogated if it happens. Holmes squats, swings the ball back and forth dramatically, and tosses it behind himself. "He wasn't going to talk anyway," says Holmes.
  • Zoey 101: This is the plot, or sub-plot, of several episodes (commonly, girls vs. boys, but also guys vs. guys, everyone vs. Logan)
  • An arc in the first half of the first season of Brooklyn Nine-Nine revolves around a bet between Detectives Jake Peralta and Amy Santiago over who solves more felony cases; if she wins, he gives her his beloved car, if he wins she agrees to go on a date with him. When Peralta wins, he intends on using the date as an opportunity to prank and humiliate her, but it quickly becomes clear that it's actually unresolved feelings he has for her bubbling up to the surface.

  • A Radio 4 comedy series about "books you've never heard of, but which sound strangely familiar" opened with the story of a stand-up comedian who accepted a drunken bet to stay at every Travelodge in Britain, only to realise he was on a spiritual journey. Parody of Round Ireland..., Are You Dave Gorman, etc.

  • George Bernard Shaw's play Pygmalion, which was turned into the musical My Fair Lady, has Colonel Pickering betting his friend Higgins, professor of phonetics, that he can't make good on his boast that he could turn Cockney flower girl Eliza into a Duchess.

  • Girl Genius: Why does Mechanicsburg have a cathedral? Because the Prince of Sturmhalten at the time of construction bet the Heterodyne lord of the time that he wouldn't build one. The prince said that if the cathedral was built, he'd eat his hat. The Hash House Lingo for a hat sandwich is a "Prince of Sturmhalten's Big Bet".
  • In Tower of God, this trope is used several times:
    • First a small bet between Lero-Ro and 25th Baam on who will pass a barrier first. The winner got to ask the loser some questions.
    • Anak and Androssi made a competition out of who would beat the bull first. The former wagered her Cool Sword, the latter herself.
    • Prince wagered Yeon to whoever would win the Shinsoo Competition, thinking it would be him. He came in second, his score topped by a sixfold by Viole.

    Western Animation 
  • An episode of The Flintstones revolves around the revival of Fred's gambling addiction (never mentioned in any other episode before or after) triggered by a bet with the newspaper boy.
  • South Park: Cartman formed a massively successful Christian Rock Band just to win a bet that he could win a platinum record before Kyle could. Cartman's band becomes wildly successful, but he loses the bet because the Christian Rock industry awards myrrh records instead — so he angrily denounces Jesus in front of his own fans.
  • Hurricanes: Jackson Black is a gambling addict. Knowing about that, Stavros Garkos managed to win Black's soccer-themed resort and his eco-sphere in a rigged roulette game. Since the terms of their bet included that, every time Black lost, he'd be allowed to try to recover his losses in another bet, he decided to bet on the upcoming Hispanola Hurricanes versus Garkos Gorgons soccer game. Black would win it all back if the Hurricanes won, which gave Garkos, who owns the Opposing Sports Team, another motive to sabotage the Hurricanes.
  • In Gravity Falls, Stan and Mabel make a bet on who could make more money: Mabel while running the Mystery Shack, or Stan while on vacation.
  • In The Simpsons, Homer and Flanders made a bet when both of their kids were competing against each other in Mini-Golf: If their kid doesn't win, they have to mow the other person's lawn in one of their wife's dresses. The kids call a draw, and thanks to Exact Words, they both have to do it

    Real Life 
  • Real life example: Roger Zelazny wrote A Night in the Lonesome October because someone bet he couldn't get readers to root for Jack the Ripper as a hero. The resulting novel won him both the bet and a Nebula Award nomination.
  • Jim Butcher, author of The Dresden Files, began his other series Codex Alera because of a bet. He was in a debate (described as 'the kind where you hit capslock and mash the keyboard') with another writer on a message board over the 'sanctity of the idea'. The unknown other party said that if you have a great idea then it doesn't matter how bad your writing is, you can turn it into something publishable. Jim believed that no matter how tired and overdone the idea, if you're a good enough writer you can make it great. The other party challenged Jim to 'put his money where is mouth is' and turn a bad idea of his choice into a book. Jim (being 'quite the internet loudmouth') said that he would take any *two* of the other person's bad ideas and combine them into something great. The ideas? The Lost Roman Legion...and Pokémon. And he did it.
  • Tony Hawks, twice, each time getting a book out of it. The first was Round Ireland with a Fridge, the second Playing the Moldovans at Tennis, the latter is a very interesting look at a country with a truly messed up economy and has started charitable donations to help out a bit.
  • H. Rider Haggard wrote King Solomon's Mines on the basis of a bet with his brother, who said H. Rider couldn't write a novel half as good as Treasure Island, the current bestselling pageturner of the day. Whether King Solomon's Mines is as good as Treasure Island is up to the reader, but Haggard's book sold so well publishers had trouble keeping up with demand.
  • Dr. Seuss wrote Green Eggs and Ham on a bet he couldn't write a story using just fifty distinct words.
  • Stephen Hawking, after deducing the existence of black holes, bet Kip Thorne that they didn't actually exist. He lost the bet.
  • George Lucas and Steven Spielberg once made a bet over Star Wars: A New Hope and Close Encounters of the Third Kind: they bet 2.5% of their film's proceeds that the other film would be more successful than their own. Steven Spielberg is still receiving proceeds from the first of the Star Wars movies.
  • A celebrated anecdote involving Calvin Coolidge, the 30th president of the United States and a man of few words. A female reporter told Silent Cal that she was bet by her editor that she couldn't get at least three words out of him. His response?
    "You lose."
  • Cole Porter famously bragged at lunch one day that he could write a song on any subject. The friends he was dining with challenged him to write something based on the next thing they heard in the restaurant. The waiter at an adjoining table then said to the person at that table "Miss Otis regrets she's unable to lunch today". The song, Miss Otis Regrets, is about a socialite who kills her lover and is then lynched by a mob was written in 1934, and is still popular today, some 80 years later.
  • Prior to the Trinity test, the first test of a nuclear weapon, the scientists were making bets on what the yield of the device would be. While the final estimate was very close, one of the scientists was taking side bets on the destruction of the entire state of New Mexico, right in front of the governor of New Mexico, who was in attendance (and suitably terrified).

Romance Examples:

    Anime & Manga 
  • In an episode of the Future GPX Cyber Formula TV series, Randoll asks Hayato what he thinks of Asuka and earlier he makes a bet with her that if he wins the Spanish Grand Prix, he gets her kiss. He didn't.

    Fan Works 
  • The pro wrestling story But It's A Whole Canadian Dollar is a comedic take on Chris Jericho and Christian's bet over Trish Stratus and Lita seen in the Pro Wrestling folder.
    • The story spawned a sequel, But It's A Whole Canadian Dollar 2: The Un-Nailables in which Jericho and Christian make another "who will score first" bet: Jericho with Stephanie McMahon, or Christian with Molly Holly.

  • In She's All That, Zack Siler bets his best friend Dean Sampson that he can turn the girl of Dean's choosing into the Prom Queen. Zack loses, but the payoff is hilarious.
  • Parodied mercilesly in Not Another Teen Movie.
  • 10 Things I Hate About You (prom again)—slight variant. Here it's not a bet but a bribe—Kat's sister isn't allowed to date until she dates, wannabe suitor arranges for Patrick to be paid to take Kat out. The part where she finds out about it works out pretty much like the bet trope.
  • Worth Winning (get engaged to 3 women)
  • Bet Me (pants version)
    • Subverted, in that Cal didn't actually make that particular bet. As he says repeatedly. Played straight in that he did make multiple other bets (and passed the profits straight on to Min; is that another subversion?).
    Min smiled cheerfully at David. "I know Cal won it," she said, "but we have this unwritten rule that I get all the money he wins on me. I'm picking up quite a bit of spare change that way, so this—" She looked at the check and almost dropped her comforter. "Oh, my God."
    "Not ten bucks," Cal said, yanking up the comforter before she lost it.
    Min looked up at him, appalled. "You bet ten thousand dollars you could get me into bed?"
    "No," Cal said. "I'm going to get a T-shirt made that says, 'I did not make that bet.'"
  • Crazy In Love (get her to island makeout spot)
  • How to Lose a Guy in 10 Days is about a woman who writes "How to" articles for a magazine. She wants to write "real" stories, with actual substance, so her editor tells her to write the titular article. The male lead just wants a woman to show off as a successful relationship so he can be in charge of his advertising company's big diamond account. Note that while both are just trying to further their own career goals, the woman is depicted as motivated by creative integrity, while the man is doing it just for money.
  • Little Darlings revolves around a bet between two girls as to who can lose their virginity first.
  • In Cruel Intentions, the whole plot revolves around a bet two step siblings make. Kathryn promises she will sleep with Sebastian only if he manages to sleep with Annette (the headmaster's daughter) before school begins. Sebastian ends up falling in love with Annette instead.
  • Jocks from two rival frats bet on who'll be the first to bed a gorgeous woman staying at the same resort in Fraternity Vacation. Subverted in that neither contender even comes close to success, and both fake evidence to the contrary; she instead winds up with a nerd they'd only dragged along because his dad paid for the trip.
  • The Big Bet is all about this trope where the lead must bed the new girl in school or lose his car.
  • The latter part of Dirty Rotten Scoundrels revolves around a bet between Steve Martin and Michael Caine's characters over who is the better seducer/con-man. The mark WINS; turns out SHE was the infamous con artist mentioned earlier, and was onto them from the start, playing along for the fun of it
  • In The Book of Life, La Muerte and Xibalba have one concerning who Maria will marry. The former backs Manolo, while the latter backs Joaquin. The winner will take over the Land of the Remembered.

    Live Action TV 
  • In the Scrubs episode "My Best Laid Plans", Dr Cox learns the Janitor has a crush on Eliot, and bets his Porche against the Janitor's van that it'll never happen. The usual plot is subverted when the Janitor simply explains the situation to Eliot and she jumps at the chance to annoy Dr Cox ... and then inverted when the Janitor falsely claims Cox wants to see them on an actual date before he pays up.
  • In Drop the Dead Donkey Damian and Henry bet Dave he couldn't get Joy to sleep with him. It actually rebounds more on Damian and Henry more than Dave.

    Professional Wrestling 
  • In the WWE, Chris Jericho and Christian bet each othernote  that they could hook up with Trish Stratus and Lita respectively before the other did. Naturally, the ladies were quite unimpressed with said bet, but Jericho ended up developing feelings for Stratus. This being Professional Wrestling, the end result was Trish turning heel, kicking Jericho in the nuts and siding with Christian.

  • In Guys and Dolls, Nathan bets Sky that he won't be able to get Sarah (a pseudo-Salvation Army lassie) to go to Havana with him. Romance ensues, but Sarah returns to find her mission raided because Nathan has been holding a crap game there. Subverts the usual play in that he tells her straight in Havana about the bet, which doesn't bother her much. It isn't until the crap game that the "boy loses girl" portion of the plot begins.

    Video Games 
  • Joshua from Fire Emblem: The Sacred Stones is a Gambling Addict and his supports with Natasha revolve around making bets. In their B support, for example, he bets that she's going to fall for him, sooner or later. In their A support, she tells him that he has won that bet, after he made a bet that he would make her happy, essentially proposing to her.
    • Even his recruitment, done by talking to him (when he's still an enemy unit) with Natasha, hinges on a bet. Although it implied that he rigged that particular coin toss so he wouldn't have to kill her.

  • The Wotch had Robin bet that he would ask out the next girl he saw. Naturally, that just happened to be his longtime Stalker with a Crush Cassie.

    Western Animation 
  • Drawn Together has a chapter where Captain Hero bets with Spanky Ham he will get laid with Princess Clara's retarded sister. And even more so vice versa.
  • South Park has a chapter that reveals Ms. Choksondik's only date in her life was with a guy who lost a Super Bowl bet.
  • The Spectacular Spiderman:
    • At one point, Peter makes a bet with Flash Thompson that he'll have a date for the upcoming school dance to show his confidence that he actually has one. However, his intended date cancels. When Peter ends up at the dance with the extremely attractive Mary Jane Watson, Flash tries to break the two up by telling Mary Jane about the bet. However, in a brilliant and downright awesome subversion, MJ doesn't care in the slightest, even making crack to Flash about the fact that he lost. Of course, it helps that she's probably aware that Peter's Aunt May set up the whole thing, plus MJ knows that she's hot and Peter would have been willing to go out with her, bet or no bet. Flash, not wanting to be the only one dresses as a cheerleader while honoring the bet, forced his teammates into similar outfits.
    • Liz Allen's brother Mark also has a gambling problem, which leads to him becoming the Molten Man. In his second episode, Spider-Man takes advantage of his gambling weakness to taunt him.
    Spider-Man: Hey Molten Man! Bet you can't hit me from here with a lava ball!
    Molten Man: I'll take that bet!
    *throws lava ball, only for Spider-Man to pull the Mysterio robot into his line of fire*
    Spider-Man: Sucker!