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."

- Rocky and Bullwinkle

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.

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. If the bet is in any way formalized, expect a Bookie to be involved somewhere. If we never see the bet being made, but only see the loser pay the winner after the event, that's a Side Bet.

Not to be confused with the multi-Crossover/Alternate Universe Fanfic story cycle from the late 1990s and early 2000s also collectively called The Bet.

General

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

Anime and Manga

 * In the Pokémon Special manga Ruby and Sapphire made a bet to accomplish their goals in 80 days.
 * Also, in the Emerald arc, Emerald made a bet with the Frontier Brains that he will beat them in seven days.
 * In Hime-chan no Ribon 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. The bet itself was getting if he succeeded.
 * In Yu-Gi-Oh, Solomon Mouto was known to be one of the greatest gamblers who ever lived, his luck even greater than Jonouchi's. After winning every game of chance he knew of, he made a bet with himself that if he ever lost one, he'd retire, open a store, and wear overalls for the rest of his life. (At the time the series takes place, he runs a card shop and overalls are his standard attire. One can only assume he eventually lost.) He still made occasional small wagers, like betting his old friend Arthur a chocolate shake that he could find all the cards for the Ancient Dragon combo before Arthur could. (He won that one, and later used the actual combo in the Grand Prix arc.)

Comic Books

 * At least three of the Asterix 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 In Belgium, 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, and they seek out Julius Caesar to judge. Hilarity Ensues.

Fan Works
"Crump: Good luck, fellah, You're gonna need it! Andy: I think I'm more than capable of winning. Crump: Bet you five bucks and a pizza you can't."
 * This is the central framing device -- and namesake -- of the late 1990s/early 2000s fanfic cycle The Bet. In it, a collection of gods, demons, spirits and the occasional mortal are competing to see who can cause the greatest divergence with the smallest initial change to an Alternate Timeline to any of a few "standard" universes -- including but not limited to the Canon versions of Ah! My Goddess, Ranma ½, Sailor Moon and Tenchi Muyo! Ryo-Ohki.
 * In a late chapter of Yu-Gi-Oh! The Thousand Year Door, Redux, Andy is about to go up against the Big Bad of the fic, and is trolled by one of her henchmen:


 * Andy doesn't say anything to indicate he agrees to this, but true to Crump's prediction, he loses the duel; the Big Bad is eventually taken down in an epic final confrontation, and in the epilogue, Crump (who is now in jail) is brought a pizza and an envelope with a $5 bill and a note presumably from Andy that reads, "I always keep my side of a bargain." Unfortunately for Crump, he quickly loses his appetite.

Film

 * "Nobody can eat fifty eggs!" Except for Cool Hand Luke.
 * Ocean's Twelve 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  ) on what will happen if they ruin a rich man's life and let a poor man take his place.
 * 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 Avengers: Nick Fury offers to bet Steve Rogers $10 that there are 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.
 * In The Three Stooges short "Hoi Polloi", a rich guy named Professor Richmond subscribes to the theory that environment and not heredity dictates social behavior, and bets another rich guy named Professor Nichols $10,000 that he can train three common folk into acting like refined gentlemen. Unfortunately, his test subjects are the Stooges, and at the formal gathering where he is to present the results of his experiment, it backfires completely. Not only do the Stooges act as they always do, but at the end of the short, all the other guests are acting like them. Naturally, Richmond has to pay up, and even the Stooges are disgusted by it all. Moe says it best when he says it serves them right for "associating with the hoi polloi".

Literature

 * In Mark Twain's short 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 Eighty 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- so yes, this is Older Than Radio.
 * 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.
 * 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 is about a bet: the protagonist bets $50 (in 1973) that he can eat one worm a day for fifteen days.
 * 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.
 * Discworld:
 * 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.

Live-Action TV
"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)"
 * 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 roommate Danny he can find 54 other Dave Gormans.
 * 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 Fiancée was essentially a bet between the network and the lead woman. She had to maintain the lie that a paid actor was her fiancée 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 episode The Human Bomb.
 * 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.
 * 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.
 * "Challenge accepted!"
 * One Drake and Josh episode titled "The Bet" had Drake and Josh betting they could quit they're bad habits longer then the other, in this case: Drake's addiction to junk food and Josh's addiction to video games.
 * 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 and 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:


 * 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.
 * In the second episode of How to Rock, the members of Gravity 5 make 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.
 * In Yo Soy Betty, la Fea, Betty's first sexual experience was with a neighborhood guy who only dated and bedded her because of a bet; the reveal of it destroyed her already fragile self-image.
 * In an episode of Mr. Belvedere, the title character bets George he can give up junk food longer than George can give up smoking, the winner being the "better man". By the end of the episode both need it too much and cheat, catching each other in the process, the results being George winning the bet by about 10 seconds. In The Stinger, Belvedere writes that the bet may have helped George kick the habit completely, and he himself has managed to cut down to half-a-pack of cookies a day.
 * The first season of Brooklyn Nine-Nine focuses heavily on the bet between Amy and Jake on who can obtain the most arrests.

Radio

 * 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.

Theatre
"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!"
 * 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.
 * 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.

Web Comics

 * Girl Genius: Why does Castle Heterodyne have a chapel? 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 chapel was built, he'd eat his hat. The Hash House Lingo for a hat sandwich is a "Prince of Sturmhalten's Big Bet".

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 gold record before Kyle could. Cartman's band becomes wildly successful, but he loses the bet because —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.
 * Gravity Falls the wager between Mabel and Stan in "Boss Mable":
 * The Terms: If Mabel earns more money running the Mystery Shack than Stan can in three days while on vacation, he'll let her be boss for the rest of the summer and sing an "apology song" that Mabel wrote. If Stan returns from his three days vacation with more money than Mabel could earn, Mabel will have to wear a t-shirt with the word "Loser" written on it all summer.
 * The Result: After Mabel becomes Drunk with Power and uses underhanded tactics, they got a net worth of $1 . However, Stan loses all the money he makes in a 'double or nothing' segment on a game show. The word he fails to guess was "please", the word he mocked Mabel for using. However, everyone (Mabel included) agree that Mabel will not run the Shack as she realizes she cannot. Nevertheless, Stan still does the apology dance. Funnier still, he has to repeat it until he gets it right, taking at least 31 tries.
 * The Owl House is a Spiritual Successor to Gravity Falls, and has a lot of bets. Eda even has a logbook detailing past times she made a bet with King, and won each time, this leads to:
 * Episode Three:
 * The Terms: If King proves he can be a better teacher to a slug-like creature than Eda is to Luz, Eda has to wear a dunce cap and live in the tool shed. If he can't, his name is officially changed to Mr. Wiggles.
 * The Results King initially wins, Eda begrudgingly accepting the punishment, but once he runs out of food to feed the now-giant slug, it turns on him. Seeing as Eda saves his life as a result, they agree to forget the whole thing.
 * Episode Five:
 * This bet is made by Luz and her rival Amity after the former challenges the latter to a Wizard Duel. If Luz wins, Amnity has to apologize to King for ruining his cupcake and admit - in public - that humans can become witches. Amnity wins, Luz has to give up learning magic forever, and to make sure she complies, places a Magically-Binding Contract on both of them.
 * The results. Eda and lilth both cheat to help their respective proteges win, so Luz and Amnity are disqualified. This leads to a real duel between Eda and Lilith, while Luz and Amnity have a heart-to-heart talk for the first time.
 * Episode 8
 * The Terms: Eda does a three-person Freaky Friday Flip on herself, King, and Luz (Eda becomes King, King becomes Luz, Luz becomes Eda) and states that whoever has the easiest time living with the new body and identity doesn't have to help clean the house.
 * The Results: All three lose. Eda is nearly turned into a lobotomized living doll by some Evil Old Folks who think King's body is cute, King is nearly killed by a group of teenagers after trying to get revenge on them with Luz's body, and Luz uses Eda's magic far too blatantly, getting herself arrested and nearly conscripted into the Emperor's Coven by Lilith. It's only via a series of Contrived Coincidences that the trio manage to find each other and change back. And they all have to clean the House, which thanks to Hooty, has become far more messy while this was happening.
 * Happens Once Per Episode (at least) on Xiaolin Showdown, the title of the cartoon being the mystical challenge that a warrior can use to take a Shen Gong Wu from another. The challenge can be practically any sort of contest the challenger can envision - a footrace, sumo wrestling, basketball, bird-catching, ice hockey, you name it, and each competitor is allowed to use the wagered Shen Gong Wu. The Powers That Be provide any equipment needed, and also warp the area where the participants are standing to make it more exotic, and often more dangerous.
 * Also, if one is challenged and feels cocky, he can "double-dare" the challenger with a Shen Yi Bu Dare, where two Shen Gong Wu are wagered, and the area is even more hazardous. Again, each competitor is allowed to use both wagered items. This only occurred five times in the series, Master Fung claiming after the first time that it hadn't been done in centuries due to the difficulty.
 * The rarest variation is the Shen Yi Bu All In, where each competitor wagers every Shen Gong Wu in his possession, but in this case, may only use one during the contest. This wager was only made once in the series.
 * In an episode of Duck Dodgers, Cadet (ie, Porky) makes a bet with Queen Tyr'ahnee as to whether Dodgers can beat Martin in a spaceship race. Initially he wagers the contents of his wallet over her necklace, but as the race heats up she raises the ante to 100 million cheeseburgers. While Dodgers wrecks his ship, he still crosses the finish line first, so Cadet wins the bet.

Real Life
""You lose.""
 * 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 the Codex Alera because of a bet. In a debate between him and a friend, he said a writer was only really any good if he could take a bad idea and turn it into a good story, so the friend dared him to take what he considered two of the worst, most overdone ideas and turn them into a book. 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 the same fifty 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?

Anime and 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.

Comic Books
"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.'""
 * At one point on The Spectacular Spider-Man, 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.
 * This was adapted into the cartoon of the same name, where Flash, not wanting to be the only one dresses as a cheerleader while honoring the bet, forced his teammates into similar outfits.
 * 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?).

Live-Action TV

 * There is an episode of Cheers where Sam and Woody make a bet as to who can be the first one to convince Jessica to kiss him; Carla acts as mediator, stating said kiss must last at least 5 seconds and be given willingly. After several halfhearted and lame attempts, Rebecca catches on, and tricks them into kissing each other. In front of the whole cast, no less.

Film

 * 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.
 * Parodied mercilessly 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 three women)
 * 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 fall in love with him so he can be in charge of his advertising company's big diamond account. Note that the woman is only doing it out of 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 stepsiblings 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.
 * Likewise Dangerous Liaisons, a more straightforward adaptation of the same book / play.
 * 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.

Professional Wrestling

 * In the WWE, Chris Jericho and Christian bet each other 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.

Theatre
"Sky Masterson: My father told me, "Son, I don’t have much money to send you out into the world with, so I’ll give you some advice. Sky Masterson: If you ever come across a man that says he can make a jack jump out of a sealed deck of cards and spit cider in your ear, do not bet this man. Sky Masterson: For as sure as you stand there you will end up with less money and cider in your ear.""
 * 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.
 * A Con Man version is also presented:

Web Comics

 * 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.
 * 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.
 * Also, there is an episode where Cartman bets with Kyle that he will win a platinum album before he does.