Bob and Alice are at the carnival on a date...or not. They see one of those popular carnival games, and Alice starts eying one of the prizes, usually a stuffed animal. Bob realizes that he has a chance to prove how manly he is and give her a present at the same time. It's a win-win! The catch? The Rule of Drama and Rule of Funny say that Bob can't get it on the first try. There are five possible outcomes to this trope:
- Bob wins the prize on his first try and impresses Alice.
- Third Time's the Charm: It takes Bob at least three tries before he wins. Bonus points if Alice cheers him on.
- Epic Fail: Bob wastes all his money trying to win the prize. Alice just giggles, kisses him on the cheek, and thanks him for trying.
- She wins the prize: Bob tries and tries, but can't seem to get it. Alice gives it a shot and wins on the first try!
- The rival wins the prize for her: Oh, this is the lowest of the low. Bob tries to win it, then Charlie comes along and wins it for her!
There are other possible outcomes, but these are the most common. Usually is a boy gaining (or trying to) a prize for a girl, but also this can be seen in a girl getting the prize for the boy or an adult (mostly parents) gaining it for a child.
Carnival games used for this trope are usually strength tests, which amplify the hope Bob has to prove his manliness (hey, that's actually a real word). Games of chance are sometimes used as well. Also this can count for toy grabber machines that usually can be found on amusement parks and carnivals, too (but seen also in malls).
- In My Teen Romantic Comedy SNAFU, Hachiman Hikigaya and Yukino Yukinoshita go out in a Not a Date searching a good present for Yui Yuigahama. Then Hachiman tries to win a plush for Yukino in a toy grabber machine, but ended paying the machine owner to get a plushie for her.
- Kaguya-sama: Love Is War: While hanging out with his crush Tsubame during the culture festival, he ends up winning a large heart-shaped cookie and offers it to her as thanks for all the times she's helped him out. What he doesn't know is that giving someone a heart shaped object during the culture festival is a sign of eternal love, so the entire school interprets it as a love confession. In a bit of a variation, he gets it on the first try.
- In Archie Comics, Betty or Veronica have occasionally asked this of Archie.
- In an issue of Cherry Comics, Cherry's date attempts to win her a teddy bear at a shooting gallery at a carnival, but loses due to the game being rigged. He later attempts to steal one for her and gets beaten up for his efforts. Cherry, meanwhile, obtains a teddy bear by sleeping with the guy who own the carnival.
- One of the stock themes in Donald Duck comics. It's always about Donald attempting to make Daisy impressed and/or favourable, and the super lucky Gladstone is often included as a depressingly successful, sometimes highly unsportsmanlike, rival.
- Pony Courtship Rituals has Chrysalis trying to win a doubly rigged game. It takes many tries, but eventually she overpowers the cheating by brute force.
- In a non-romantic variant, Unexpected Surprise has Adrien get Emma a black cat plushie the first time he babysits her.
- Invoked in My Huntsman Academia. Yang and Izuku stop by a carnival while playing a game of romantic chicken during Color Week. She gives him tips on how to win a rigged game at one of the stands and asks him to win her a prize, waiting to see what he gets for her to watch his reaction for laughs. While hanging out again in Mountain Glenn, she returns the favor, winning him a Toshinori plush while making him blush with her usual flirtatiousness.
- Darkman - while the main character Peyton and his girlfriend visit a carnival, he plays a game to try and win a pink elephant doll for her. However he argues with an employee over whether he rightly won the prize or not, which results in Peyton gruesomely twisting the carnie's fingers.
- Hot Fuzz: Nicholas uses his Improbable Aiming Skills with air rifles to win a large monkey for Danny.
- Invoked in Mr. & Mrs. Smith (2005): John and Jane, two of the world's best assassins, visit a funfair for a date, where John tries to win a price for his girlfrend at a shooting gallery. Because he tries to keep his cover, he deliberately misses his first shot. But when Jane hits the bullseye on her first try a shooting contest ensures.
- In the movie Remember Me, the male lead ends up buying the stuffed animal for his girl. She thinks he cheated. He says he won.
- In Ladder of Swords Don DeMarco wins a blue fluffy teddy bear for Alice.
- In Magical Legend of the Leprechauns a variant is used. Jack is at the carnival, and nobody except the near-blind pastor likes him (he accidentally saw Kathleen bathing in a pond). The pastor is failing at the rigged ring toss game (the post is so close to the diameter of the ring that you'd have to drop it from directly above to have any chance of winning), so Jack volunteers to toss for him, hoping to win some brownie points with Kathleen. His invisible leprechaun friends make the ring land all the way down the post, and the pastor picks a stuffed pink elephant as his prize. Kathleen is not impressed. It'll take a few more scenes for her to warm up to Jack.
- In Watch Out, We're Mad!, a mobster in an amusement park is hanging out with a couple of girls gaining prizes for them in the games. Sadly for him, Ben and his partner Kid goes after him, and everytime the mobster makes a record, Ben plays the game after and destroys it to the surprise of all the crowd (the mobster included).
- Journey to Chaos: During Dnnac Ledo's Festival of Arin's Ascension, Nolien tries and fails at a shooting gallery. Tiza wins more easily and consoles him by saying she's just better at carnie stuff than him, "just like how you're better at tent stuff than me". Eric teases him for carrying the giant stuffed bunny she won, and remarks that he'd like to win one like it for Annala.
- In Lois & Clark when the title characters were "not on a date", Clark did this. Before you think he was being a jerk pretending to be weak, he was suffering the aftereffects of being exposed to kryptonite for the first time.
- Played with and possibly Invoked on an episode of the The Andy Griffith Show, Opie complains to Andy (who is both Opie's father and the local sheriff) that the carnival shooting gallery is rigged so Andy goes in undercover with Thelma Lou, pretending to be a local yokel trying to win a prize for his gal.
- There is a sketch on Saturday Night Live that pokes fun at this where legendary quarterback Tom Brady struggles to win a prize for his girlfriend at the carnival.
- In Tim McGraw 's song "I Like It, I Love It", he describes all the things he does to impress the girl he's infatuated with. The first line of the song includes:
"I spent 48 dollars last night at the county fair. I throwed [sic] out my shoulder but I won her that teddy bear."
- Kane tried to get a toy from a toy grabber machine for a kid in an arcade room. After an unsuccessful attempt, he just broke up the machine and gave the kid a lot of toys from there.
Kane: Stay back, kid.
- During Shizune's Act 1 ending in Katawa Shoujo Hisao is "persuaded" by Misha and Shizune to try his luck at ball and bottle game at the Festival and tries to win the two girls a pair of stuffed cat dolls. He eventually wins one for Shizune but is forced to stop when his arrythmia acts up.
- In the cutscene that plays when you first enter the Carnival room of Stay Tooned!, Fiddle tries to win a prize for Katrina at the bottle toss game. When he fails miserably after just one try, Katrina tries and succeeds at knocking both the bottles and Fiddle down every time. The cutscene ends with Katrina having won many stuffed animals and having Fiddle hold them for her.
- The Witcher 3: Wild Hunt DLC Heart of Stone, the ghost of Vlodimir Von Elrec spends the one night he's given to possess Witcher Geralt at a wedding. The celebration includes different competitions, all of which Vlodimir attempts to win in order to impress Geralt's date, Shani. If Vlodimir-as-Geralt is able to win the hog wrangling competition, Shani receives a stuffed animal as a prize.
- Unwinder's Tall Comics takes this in a surreal direction. Mildred really really wants a stuffed doll from a game at the County Fair, so Barbecue Sauce tries to win a knock-over-the-target game for her. But instead of throwing a ball at milk jars, Barbecue Sauce is supposed to throw a toy airplane at a model of the World Trade Center. Then the game turns out to be completely unwinnable: it's actually just an excuse for the carnie to lecture people on how 9/11 was an inside job.
- Played for Laughs in Despicable Me where Agnes wants a unicorn plushie they have on display. The girls try twice and fail - Agnes even hits the target once but was unable to knock it down. When Gru tries it, he takes out his laser blaster and blows up the stall. Agnes gets her unicorn.
- As the quote from Teen Titans indicates, Beast Boy won a prize for Raven in one episode. She was less then thrilled and discarded the prize at the first opportunity five seconds later. It wasn't romantic in nature...no really, it wasn't!
- Gravity Falls: Dipper tries to win a stuffed animal for the girl he has a crush on, Wendy, by knocking down glass bottles with a baseball. He knocks them down, but the baseball hits her in the eye. Then, Robbie, Dipper's rival who also likes Wendy, shows up with a sugar cone to help ease the pain in her eye while Dipper was getting ice.
- Olive Oyl has Popeye and Bluto win her prizes on various occasions.
- Principal Skinner tries to win a prize for his Mother in one episode of The Simpsons.
- Peter did this for Liz in one episode of The Spectacular Spiderman. Naturally, the carnival was attacked by supervillains soon afterward.
- Gender Inverted in the Kim Possible episode Emotion Sickness. Kim, under the influence of a moodulator set to "lovestruck," wins a carnie game plushie for Ron.
- Seen a couple of times on Hey Arnold! between Arnold and Lila, when he gained (or tried to gain) a prize this way for Lila.
- Gender flipped in the King of the Hill episode "Chasing Bobby" during a scene at a movie theater.
*Bobby and Connie walk into the lobby with Bobby ecstatically holding a stuffed animal.*Bobby: And they say nobody beats the claw machine!Hank: That's great, son. Now give it to Connie.Bobby: No, she won it for me.