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While in [[O-Hina Town]], {{an|Misty}} and [[Jessie]] enjoy the perks of the [[Princess Festival]] while in [[O-Hina Town]], a holiday with events, shopping sales and discounts, festivals, and games that are exclusively for women. Misty goes on a shopping spree, making {{Ash}}, {{an|Brock}}, and even {{AP|Pikachu}} carry her purchases. At a local park, Jessie shows off her expensive finds, including food and clothing, and hopes the Team Rocket company credit card can handle the pressure. Just then, a {{TP|Jessie|Lickitung}} appears and swallows Jessie's food. Irritated, Jessie throws a {{i|Poké Ball}} and abruptly [[Caught Pokémon|catches]] it, much to {{MTR}} and [[James]]'s surprise. Jessie then drags James and Meowth with her to do more shopping.
At a store, Jessie encounters Misty, and they fight over a dress, only to have another shopper grab it while they aren't looking. They quickly forget about it when an announcement is made over the store's intercom about the [[Queen of the Princess Festival]] contest. Jessie and Misty decide to enter, fueled by their desire for the prize, a set of Pokémon Princess Dolls. The other prize is a picture with a movie star named [[Fiorella Cappuccino]], but they don't show interest in that.
During the competition, Fiorella, an announcer, and a line of pretty girls dressed in kimonos and crowns, including Jessie and Misty, stand on a stage. The announcer reveals that the contest isn't just a beauty pageant, it is also a Pokémon battle competition. The contestants are split into divisions, and they must use four {{OBP|Pokémon|species}} to {{pkmn|battle}}. Misty then begs Ash and Brock to let her use their Pokémon for the contest, and they reluctantly loan Pikachu, {{AP|Bulbasaur}}, and {{TP|Brock|Vulpix}} to her. When Ash is confused as to why Misty wants to meet Fiorella, she explains that she just wants the dolls, because [[The Sensational Sisters|her sisters]] all had their own doll sets, while she only got their hand-me-down dolls, which were broken by the time she got them.
Misty wins several matches with Ash and Brock's Pokémon, as well as {{TP|Misty|Staryu}}. Jessie also wins matches with {{TP|Jessie|Arbok}}, {{TP|James|Weezing}}, and Meowth. Misty and Jessie then face off in the finals, but not until after Jessie reminisces about her hatred of the Princess Festivals because, like Misty, she never had a Pokémon Princess Doll of her own, while all of the other girls did. The story brings the emotional trio to tears, and James and Meowth give her support. During the match, Pikachu makes quick work of Arbok, Weezing, and Meowth. At first, Jessie and James lose hope that she will win the contest, but Meowth reminds her that she caught a Lickitung earlier, and the battle continues. Lickitung easily defeats Pikachu, Bulbasaur, and Vulpix with a confusion-inducing {{m|Lick}}. Then, Misty tries to send out {{TP|Misty|Staryu}}, but her {{TP|Misty|Psyduck}} pops out instead. At first, Misty is in despair, thinking that she can never win now. Just then, in an unexpected turn of events, Lickitung's attacks give Psyduck a headache, triggering its potent Psychic powers. Misty wins the match and the Queen of the Princess Festival Contest with Psyduck's {{m|Confusion}}, while blasting off {{TRT}} in the process.