After what seemed like years of traveling, Ash, Misty, Brock, and Pikachu have finally reached Goldenrod City, the home of Goldenrod City Gym, and hopefully, Ash's 3rd Johto League Badge.
Fascinated by the town's amazing size, Misty sets her sights on the local shops, while Brock focuses on what he likes best; girls. Ash tries to pull them away from all the distractions, when he finds his favorite thing as well - food. Mustering up all his strength, he resists the urge and tells the gang that he came here to win a badge, not to shop, meet girls, or eat burgers.
Much to Misty and Brock's delight, Ash finds the gym closed for the day. Brock suggests that they head over to the Goldenrod Galleria, where they can spend the day and have fun until tomorrow. Unfortunately, Brock's navigating skills prove to be useless as the gang winds up lost in a dead end. Pikachu runs back the way they came, only to cross paths with a Clefairy. As Ash picks the Clefairy up to ask if it's hurt, its owner goes over to see if Pikachu's okay. She kisses it on the forehead, telling Pikachu she knows how to make a "boo-boo feel better". Suddenly, Brock smashes his head against a wall, suggesting that she should do the same for his boo-boo. As usual, Misty drags him away by the ear, saying the girl only kisses boo-boos, not bozos.
The girl introduces herself as Whitney, and tells Ash that she'd be happy to take him and his friends to the Goldenrod Galleria. Unknown to our heroes, Whitney is also the Goldenrod City Gym Leader. She takes the gang to an underground shopping arcade and up a staircase; saying this semi-secret passage should lead them to the galleria lobby. It turns out to do just the opposite, and the group ends up even further away than they were before. Everyone runs back down and goes another route, this time landing in a Pokémon Salon. Ash, Misty, Brock, and Whitney leave on the note that they're looking for a shortcut, not a haircut.
By now, Ash is famished. Brock mentions that he'd be happy to go back to hamburger stand they saw when they first arrived in Goldenrod. Whitney tells him she knows the way, and goes through another staircase. Much to her surprise, it leads to the gang's previous destination, the Goldenrod Galleria. Whitney realizes that maybe she only knows where she's going when she doesn't know where she's going. In any case, she charges forth and tells everyone to follow her through the automatic doors. Problem is that the doors aren't automatic, as Whitney soon finds out by running into the glass
Inside the galleria, Team Rocket helps themselves to a couple dozen "free samples" of food. Not knowing what free samples are, James tries some out, and tells Jessie and Meowth that food tastes so much better when it's free. As Team Rocket enjoys their lunch, one of the employees approaches them from behind and asks them if they're going to buy anything. Jessie and James reply by performing a different variation of their motto, talking about denouncing the evils of paying for food and scarfing down free samples at the speed of light. After they're done, the employee tells them that only one of the dishes was free. The rest was not. Without any cash, Team Rocket is forced to work off their debt, selling drumsticks, turkey, and other assorted items. That's when James spots Whitney's Clefairy wandering around the store. They rush after it, hoping that they can steal it and give it to the boss. Meanwhile, Whitney apologizes to Misty for starting off on the wrong foot, and tells her that she's glad she was able to finally find a place to do some shopping. Misty says she was lucky that she only had to pick up a few little things, which is an understatement since Ash and Brock are carrying piles of boxes of her new stuff. As Whitney is about to bid the gang farewell, she finally realizes that her Clefairy is missing. Everyone, with the exception of Brock, who is lagging behind with all the paraphernalia in his arms, chases after Pikachu as it runs off to find the lost Pokémon.
Not too far away, Team Rocket sneaks up on Whitney's unsuspecting Clefairy, and after successfully bagging it, our heroes spot them. With two options, fight or flee, Team Rocket decides to flee. They head for Magnet Train Station, where they hope to get away by train. When they ask the man when the next train leaves, he replies, "a year from next Tuesday", and walks away. With no other way to go, Team Rocket uses a handcar to as means to escape. Ash tells Pikachu to give chase, who has no trouble catching up, since the handcar hovers as fast as Pikachu walks. Ash then commands Pikachu to use Thunderbolt, but before it can deliver the attack, Jessie surrenders and gives the Clefairy back. Of course, Team Rocket never gives up that easily, and Meowth bags Pikachu off guard. Whitney orders Clefairy to use Metronome, and a powerful Gust attack ensues. Pikachu is blown out of Team Rocket's grasp and back into Ash's arms. Ash decides to finish this as Pikachu unleashes a Thunder attack. The handcar and its occupants are shocked, and suddenly it starts moving at an insane speed. James figures that Pikachu's attack must've activated the electromagnetic engine in the car. Team Rocket speeds away, zooming off again.
Ash thanks Whitney for rescuing Pikachu. Whitney says she would love to have a battle with him, but Ash politely declines, saying he needs to get ready for his gym match tomorrow. Asking Ash why he didn't say so sooner, Whitney tells him she could've gotten him in today. Confused, Ash asks Whitney if she's the gym's cleaning lady. Whitney realizes that she forgot to tell Ash who she was before, so she reveals her identity as the Goldenrod City Gym Leader.
Inside the Goldenrod Gym, the referee announces the number of Pokémon that will be used for the imminent match - three on three. First, Whitney calls out Nidorina, while Ash sends out Cyndaquil. Both Pokémon appear on opposite sides of the battlefield and the round begins. Nidorina starts things off with Poison Sting, but it's stopped short by Cyndaquil's Flamethrower. Nidorina then tries to charge at Cyndaquil using Tackle, but another Flamethrower is enough to stop it and win Ash the first round. Whitney recalls Nidorina and brings out Clefairy, who uses Metronome. Expecting the worst, Ash and Cyndaquil get ready for whatever attack that'll follow. This time, the Metronome ends up being a total flop, as Clefairy is stuck using Splash. Cyndaquil begins to fire flames at Clefairy, but it surrenders. Now a one on three battle, Ash begins to get the impression that all of Whitney's Pokémon are pushovers. However, he's proven wrong when Whitney summons Miltank and its Rollout attack. Cyndaquil gets thrashed around several times before going down. Totodile is Ash's next choice, and it uses Water Gun. It connects, but has no effect. Whitney warns Ash that her Miltank's Rollout gets stronger by the moment. Totodile is hit by the devastating attack, and after one blow, the playing field is now even again; Ash only has one Pokémon left. Brock suggests that since Miltank is now wet, Ash should use Pikachu. He complies, and tells Pikachu to use Thunderbolt. However, like everything else Ash has tried, it fails to effect Miltank. Whitney commends him for the idea, but says Miltank's spinning so fast it's already dry. Ash tells Pikachu to use Agility in hopes to dodge Miltank, but it's too late. Pikachu falls, and Ash loses the battle.
Whitney congratulates her Miltank for a job well done. She turns her attention to Ash and tells him if he ever wants a rematch, she'd be happy to accept his challenge. Whitney walks away, leaving Ash and his friends to themselves. Getting the Plain Badge will not be as easy as Ash once thought.