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The episode begins right in the action, with Lillian in the middle of doing the Saffron City Pokemon Contest opening. She riles up the crowd, getting them excited for the upcoming appeals and battles and the audience response, happy to go along with the show. Brock shouts his support to Lillian from the crowd, and Max folds his arms and says that the Kanto Contests should prove interesting. Lillian then pulls out the prize for the winning Coordinator, the Saffron City Ribbon! She explains to the crowd that with this and four other ribbons, a Coordinator may enter the Kanto Grand Festival, the goal of all aspiring Coordinators.
Watching all of this from the room in which all the Coordinators gather before the Contest begins is May with Squirtle. Holding the young Pokemon in her arms, he asks it to do its best and Squirtle responses happily. All of a sudden, Harley appears and puts his hand on May's shoulder. May is shocked to see the purple haired Coordinator, who instantly starts to apologise for his 'mistake' which nearly caused May to miss entering the Contest. May tells him that she isn't fooled, and that despise all his planning, she will win the Contest's ribbon. Harley smiles smugly and waves his finger in front of May's face and tells her that it will be he, in the end, that gets the ribbon. Back in the Contest Hall, Lillian introduces the judges of the Contest; Mr. Contesta, the Head of the Pokemon Fan-club and Saffron City's Nurse Joy. Lillian then proclaims that the appeal stage is about to begin, and asks the crowd if they are ready: To which the audience cheer. Ash, Max and Brock aren't the only ones cheering their friend on however, as James and Meowth sit in one of the higher stands to cheer on Jessie.
Lillian then introduces the first appeal, and Harley walks onto the stage blowing kisses and introducing himself. Ash and Max grumble at the sight of May's rival, and Brock glares at Harley while James and Meowth do the same remembering that it was Harley that foiled their last plan. Harley smirks, and sends out his pretty buddy Cacturne. Harley orders Cacturne to use Cotton Spore, and Cacturne shoots out several small cotton spores around the stage. The audience look on in wonderment. The spores hang in mid-air, circling each other as Cacturne watches them silently. Harley, confident of his appeal, then tells Cacturne to use Needle Arm. The cactus Pokemon steps forward, into the cotton spores which still hang in mid-air. However, the Pokemon does not use the attack and stands there unmoving. The audience, including Ash, Max and Brock look on in surpriseand wonder why Cacturne isn't doing what it was told to do. Harley giggles under his breath, and clicks his fingers. Several large white spikes rip out of Cacturne's body and pierce the Cotton Spores and Cacturne steps forward with the spores impaled on his spikes. The crowd cheer, and Ash Max and Brock look on in amazement and Brock comments that that was an original use of Needle Arm. Also watching the appeal is May on the screen in the Coordinator waiting room.
Several other appeals are then shown, which include a Pidgeot, a Vileplume, an Alakazam and a Tangela. Lillian then introduces the next Coordinator, and Jessie walks on in a long red dress and a Beautifly themed mask. Jessie smiles, and sends out Cacnea. Jessie tells Cacnea that it's time, and she runs toward Cacnea and Cacnea does the same to her. As they reach each other, Cacnea jumps into Jessie's arms and hugs her, but hurting her with its spikes. Jessie bits her lip in pain as sad music plays which causes the audience, including Ash, Max and Brock to look on sad and upset at this touching hug of love and pain. Lillian is amazed by the appeal, and comments on the feeling of love and peace as Jessie and Cacnea are drowned in spotlight. Jessie, still hurting from the spikes, reminds herself that she is doing this in her goal to be a Top Coordinator. Biting through the pain, she orders Cacnea to use Pin Missile into the air. Cacnea does so, sending several missiles into the air which explode on contact with each other and cause an explosion of rainbow coloured light which rains over Jessie. The crowd cheer at the amazing appeal, and James comments that Jessie has got it in the bag judging from the audience response. The judges seem to agree, as they praise Jessie for her appeal. Lillian asks Jessie if she has anything to say, but Jessie does not response as the pain as caused her to freeze and a Chansey has to take her away on a trolley.
The next COordinator enters the stage, May and Squirtle. Squirtle looks on at the huge crowd and suddenly loses its confidence. May tells the young Pokemon that it'll be alright, and that they can do it together. May then sends out Combusken for her appeal. The fighting Pokemon somersaults in mid-air and lands perfectly. May then rips off her bandana, throws it into the air and orders Combusken to use Fire Spin and then Sky Uppercut. Combusken does so, using Fire Spin to propel the bandanna further into the air, and then jumps through the rings of fire up towards it. Reaching the bandana, Combusken uses the attack to style the bandanna back into its original form. Combusken then hits it sending it falling to the ground where May is there for it to land on her head. They then finish with a pose together. The audience cheer in response, and Lillian says that it was an amazing performance. Squirtle looks on amazed, and Ash and Max shout support from the audience stands. Harley, watching the performance from the Coordinator waiting room however, is not impressed.
Lillian points to a screen above her, which has the pictures of the Coordinators who have made it through to the next round. Jessie, Harley and May are all shown. While the battle match-ups are decided, May watches with Squirtle excited that she has got through to the next stage. Harley walks up behind her, and sniggers telling him that she won't even be able to get to the Final Stage. May says that she will, and while the two Coordinators stare at each other, a figure wrapped in bandages walks over to them. Harley steps back in surprise the person tells them that she will be the one to make it to the Final Stage. The person then rips off her bandages and reveals her identity: It's Jessie! Both Jessie and Harley then point at May and tell her that they'll knock her out.
Back in the Contest Hall, Lillian announces that the first Contest Battle is about to begin. She then points to a screen above her, picturing the two Coordinators facing off. It's Harley and Jessie who both stare at each other with confidence. The timer begins, and Harley sends out his King of Cool; Ariados. Jessie responds by sending out Wobbuffet, a choice which puzzles James. The two Pokemon face off, and Jessie smiles to herself, and thinks over her plan in her mind. Ariados will attack, and she will order Wobbuffet to counter, knocking Ariados out and winning her the battle. Harley stares at the Wobbuffet and grits his teeth- He's fully aware of Wobbuffet's abilities and doesn't want to attack. May wonders from the waiting room why they aren't battling, and Brock explains to Ash and Max that should Ariados attack, Wobbuffet can easily use Counter to send the power of the attack right back. Lillian proclaims for the Pokemon to battle, but both do nothing which annoys Jessie. Jessie then shouts at Harley, asking him why he isn't attacking. Harley refuses, and Lillian punishes both trainers for not battling by giving them both a yellow card and cutting their health in half.
The two Coordinators then shout and fling insults at each other, and Lillian says that maybe she should punish them again before Harley begs her to reconsider saying that he'll do what she says and attack. This gives Harley an idea however, and orders Ariados to use String Shot. Jessie was waiting for the attack order, and tells Wobbuffet that it's time to go as the Pokemon prepares a Counter attack... which is stopped right there as Ariados fires its String Shot on Wobbuffet, tying it up in its sticky webbing. Jessie asks what is going on, as Counter should have worked. Harley explains that String Shot isn't an attack, and since its trapped Wobbuffet anyway, it can't Counter in response to it. Ariados then pulls on the string, causing Wobbuffet to move along to the pressure. Harley, happy that his Pokemon is winning as Jessie's health bar goes down, starts to dance. Ariados copies its master's moves and forces Wobbuffet to dance along too. Jessie looks on, shocked, and asks how this could have happened as the crowd cheers at the hilarious display. Harley then tells Ariados to finish, and Ariados flings Wobbuffet into the air and catches it on its back.
The audience cheers once again, as Jessie, James and Meowth shock in disbelief.
Several battles leading up to the last are then shown, and include Squirtle going up against a Crobat, Ariados defeating a Walrien, and Squirtle beating a Weepinbell. All of these battles leads up to the last match-up of Harley and May; the third time the two Coordinators have been paired up against each other. On the stage, the two Coordinators face off as Lillian goes through her usual speech about the Final Battle and the winner receiving the Contest Ribbon. May starts off by sending out Squirtle, and Harley sends out his King of Cool, Ariados. Harley begins things straight off, as Ariados fires white webbing from its behind and swings over to Squirtle stopping right in front of its face. This causes Squirtle to step back and fall in shock. May tells Squirtle to get up and use Ice Beam. Squirtle does so, but it appears to not have mastered the attack yet and the force takes the young Pokemon off balance. Ariados then lifts itself up on and dodges the attack. Ash comments that the attack has amazing power, but Brock reminds him that it still hasn't got full control of it yet as Squirtle lies on the floor, crying and flailing around like a baby. Harley laughs at this, and mocks May and her choice of Pokemon. May pleadswith Squirtle to get back up, but the baby Pokemon continues to flail. Harley then orders Ariados to use String Shot, which it does lifting Squirtle up towards Ariados who is hanging off the ceiling. May shouts to her trapped Pokemon in anguish as Ash, Max and Brock look on feeling useless. As Squirtle squirms in Ariados' grip, Harley orders his Pokemon to use Spider Web to cover the arena. Ariados does so, sending several streams of webbing across the stage causing many sparkling webs to hang above the ground. This causes the audience to cheer as they marvel at the shiny webbing.
Harley smirks, and tells Ariados to swing Squirtle around. Ariados does so, and the string holding Squirtle snaps and Squirtle falls onto the webbing below and sticks fast. Harley smiles to himself once again as May looks on worried at her trapped Pokemon. Harley enjoys May's obvious anguish and orders Ariados to finish Squirtle off. Ariados lowers itself onto the webbing and crawls over to Squirtle along the webbing. May tells Squirtle to use Bubble to hold off Ariados, but the spider Pokemon counters by using the feelers on the top of its body to block them. May grits her teeth as her health counter goes down and Ariados crawls faster and faster toward Squirtle. Just at that moment, however, she remembers what happened before when she tried to attack with Ice Beam: The force of the attack send Squirtle flying backwards. May realises that she can use the power and Squirtle's ill control of the attack to her advantage and orders her Pokemon to use Ice Beam. Squirtle does so, and the force sends it backwards and crashing through the web. The attack also hits Ariados freezing it in a block of ice. The crowd cheer, and Brock, Max and Ash all stand up in amazement and shout support at their friend. Harley stops back in surprise as May tells Squirtle to use Bubble. Squirtle jumps onto the web it was once on, and uses Bubble, breaking the block of ice while doing so and sending Ariados sliding backwards. Harley tells Ariados to get ahold of itself and fight back, and Ariados tries to, but the ice coating which covers its webbing stops the spider Pokemon from gaining a grip. May then tells Squirtle to finish it off, and use Tackle. Squirtle slides down the web and smashes into Ariados which sends it falling toward the ground and smashing into the stage floor. Squirtle then lands on Ariados, flexing its muscles. Lillian announces that Ariados is unable to battle and that May is the winner.
May hugs her Pokemon, and Harley calls back his and walks off the stage in disgust. May is then awarded the ribbon and she, Squirtle and Combusken pose in celebration.
The episode ends with Ash, Max and Brock congratulating May and the group setting off once again for their next destination: The place of Ash's next battle in the Battle Arena.
Thanks to Alfonso for writing this for us
421: A Hurdle For Squirtle
421: Pokémon Contest! Saffron Conference (Part 2)!
May wins the Saffron City Contest, beating Harley, and earns her first Kanto Ribbon