Twenty years ago, Dawn's mom Johanna lost a Pokémon Contest to Lila from Celestic Town. That battle ended Johanna's winning streak, but Lila quit Contests and became a top Poké Stylist. Now that Dawn and her friends are in Celestic Town, she and Brock visit Lila's store but learn that Lila is out. Disappointed, Dawn heads to the Celestic Town Contest, only to find that Lila is among the competition! Lila's making her big comeback, and she puts on a great show with her Cherrim. After Jessie puts on her Jessilina disguise and takes to the stage with Yanmega to try out her Fantina imitation, it's Dawn's turn to show off her ice-skating Buneary.
After that first round, Dawn finds Lila backstage—having a video conversation with Johanna! That twenty-year old battle was the turning point when Lila decided she really wanted to be a Poké Stylist, but her competitive spirit returned when she saw Dawn's earlier Contest battles on TV. Now she's back, and she'd love to win her fifth ribbon by beating Dawn. Jessie doesn't make it to the second round, but both Dawn and Lila move on and advance to the final round without any fuss. To start off their battle, Lila's trusty Delcatty uses Substitute to get the drop on Aipom. Then, after its Cute Charm ability charms Dawn's Ambipom, it hits Ambipom with Sleep.
Things are looking bad, but Ambipom manages to wake up and fight back. However, its attacks don't always work because it's still charmed by Delcatty. Dawn keeps battling anyway and as soon as Ambipom recovers its senses, it unleashes a huge Swift move. Delcatty counters with an equally amazing Shockwave. Their attacks light up the stage, with the crowd watching in suspense as Ambipom's Swift finally overpowers Delcatty. That makes Dawn the winner! Fortunately, Lila's a good sport, and she gives Dawn and her friends a chance to pick out free outfits from her store. Once our heroes get some new clothes, it's time for them to get back on the road and head towards their next adventure!
Johanna remembers her experiences with her rival Lila. During a Contest Battle long ago, Johanna orders her Glameow to use Iron Tail, but the opposing Trainer's Delcatty disappears, the announcer exclaiming that it was a decoy and asking the crowd rhetorically where the real one is. The Chinese-dressed female orders her Delcatty to use Shock Wave. The announcer remarks on Lila's famous "Tiger Lily" smile, as she poses with a fan and blows pink flower petals away, saying "the flowers have bloomed". After this the time runs out and the winner is revealed to be Lila from Celestic Town. Johanna and Lila then shake hands and compliment each other on their performance during the battle.
Johanna recounts the story to Dawn and her friends about over the video phone. Johanna goes on to say that she had never lost a match before and Lila was the one to break her winning streak. Ash then asks who Lila is, much to Dawn's surprise. She then shows him a page in a magazine showing the grown up Lila and her Delcatty and explains she is a well-known Pokémon Stylist that designs outfits and accessories for Trainers and Pokémon. Johanna explains that she retired from being a Coordinator before she could have a rematch with Lila and so the loss still stands, however Johanna is fine with that. Brock then remembers reading that Lila's store is located in Celestic Town, and Dawn becomes ecstatic about having the chance to visit. Dawn then turns to Ash to ask if he's coming, though he is set on training for his rematch with Fantina and finding a way to counter her Hypnosis. The gang agree to meet back at the Contest Hall and part ways.
Dawn, Brock and Piplup arrive at Lila's shop and are amazed by the clothing they see there, including the outfit Wallace wore for the Top Coordinator Carnival. Dawn then goes over to the checkout point and asks the lady working there if she'd be able to see Lila. The woman apologizes and says that Lila is out for the entire day, much to Dawn's annoyance.
Meanwhile, Ash is sitting in a park with all of his Pokémon. He asks them to all try and think of a way to counter Fantina's Hypnosis, however they all end up falling asleep. Eventually Ash wakes up and is surprised to see his Pokémon asleep, and he wakes them up without hesitation to train more.
Later, at the Contest Hall, the Celestic Contest is about to get underway as Marian greets Coordinators and fans who have come to the event and introduces the panel of judges, formed by the Chief of the Pokémon Activities Committee, Raoul Contesta; the President of the Pokémon Fan Club, Mr. Sukizo; and the operator of the local Pokémon Center, Nurse Joy. After that, she shows off the Celestic Ribbon, which will be given to the winner. In the changing rooms, as Dawn struggles with her hair, a formally dressed woman with a briefcase passes through the door telling someone to hurry up, then followed by a more casually dressed woman with sunglasses, who says that she does not want to do any work today. The woman then sees Dawn's less than perfect hair and excitedly fixes it. Dawn turns to thank the woman and recognizes her as Lila, who pulls her sunglasses down and also recognizes Dawn. The first woman comes in the room and drags Lila out.
Marian introduces the Performance Stage as Dawn watches from the waiting room. The first Coordinator is introduced as the "Tiger Lily" of Celestic Town who is making her first Contest appearance in over 20 years, Lila. Up in the stands, Ash and Brock are excited to find out that Lila is making a comeback. Lila calls upon her Pokémon, and bursting from a Poké Ball with a Flora Seal is a Cherrim who, thanks to the bright stage lights, opens up to reveal its Sunshine Form. Ash then scans it with his Pokédex. Lila begins her presentation with Cherrim using Magical Leaf and Sunny Day to create the image of a beautiful green flower shape in the stadium. Brock comments that she really knows how to show off Cherrim's unique qualities, and all three judges like it as well. Dawn is amazed by the combination as well, but remembers that for today, Lila is her opponent. After a number of performances, Jessilina enters the stage promising a Fantina-inspired performance while putting on a poor French accent. Her appeal round, however, is just her Yanmega using Silver Wind to allow her to fly, very similar to her appeal with Dustox in the Solaceon Contest. Ash and Brock seem almost embarrassed to watch it and wonder what connection it has to Fantina at all, while James, Meowth, and Wobbuffet seem equally embarrassed, as do the three judges.
During Dawn's appeal, she calls upon Buneary and has her use Ice Beam to create a slide of ice that Buneary can skate on. Dawn then tells her to use Dizzy Punch, which allows her to skate on her ears, however she spins out of control and flies across the stage. Fortunately, Dawn catches her and with a smile and a pose, they cover up their mistake. The judges gave Dawn good comments.
While waiting for the results, Dawn and the others find Lila and Johanna, who had been watching the Contest on television, talking over the video phone. Lila compliments Dawn's performance and Dawn asks about the battle between her and Johanna. Lila goes on to say that it was the most important battle of her life because it helped her decide she wanted to become a Pokémon Stylist. She and Johanna agreed to go on and do what they really wanted to do and Lila went to study Pokémon styling abroad. Johanna is still surprised that Lila would enter a Contest again, so Lila explains it was because of seeing her rival's daughter on television, Lila thought she could stake winning her fifth Ribbon in a battle against Dawn, allowing her to compete in the Grand Festival. Johanna guesses there is another reason for Lila competing, and Lila explains that if she battles Dawn the way she did Johanna, she may learn something about herself.
Marian then announces that the judges are done and the eight Coordinators that got through are shown on the screen. Lila and Dawn make it through but Jessilina does not. The pairings are shown with Dawn and Lila shown at opposite ends. They agree to meet in the finals and Johanna wishes them both luck. With Lila using Delcatty and Dawn using Ambipom, they both make it to the final round. Dawn worries in her head about getting her third Ribbon and the loss her mother suffered to Lila, while Lila is quite excited about the battle. Dawn reassures herself she will have a good chance at getting her third Ribbon. With five minutes on the clock the battle begins, they both send their Pokémon and Dawn makes the first move. Ambipom spins and uses Swift on Delcatty, which he avoids with Substitute. Delcatty wraps hiself up in Ambipom's tails and uses Shock Wave, creating a rainbow flower across the stage, at which point Lila then poses her signature "Tiger Lily Smile", which appears to be quite a crowd pleaser. Back in Twinleaf Town, Johanna is pumped at the sight of the battle on the television. Ambipom breaks free with Double Team and hits Delcatty with Focus Punch, however she becomes attracted to her foe. Brock explains to Ash the effects of Delcatty's Cute Charm Ability, revealing that Lila's Delcatty is male. To make matters worse, Delcatty puts Ambipom to sleep with Sing, which catches Ash's attention. Ambipom is hit by Iron Tail and is sent flying across the stage, queuing another "Tiger Lily Smile". Delcatty continues to attack Ambipom with Shock Wave before she wakes up and counters with Swift, which Delcatty dodges the way he did before with Substitute. Ambipom manages to strike back with Double Hit, however she gets affected by Cute Charm again. Dawn tries to command Ambipom anyway, and she manages a Double Team. Lila tries to put Ambipom asleep again with Sing, but gets knocked away with Double Hit. Ambipom then snaps out of it and attacks with a huge Swift that Delcatty is unable to avoid, even with Substitute. Delcatty uses Shock Wave and the two massive attacks collide. Swift breaks through and hits Delcatty just as the time runs out. The smoke clears and Dawn is revealed to have more points than Lila. On camera Dawn speaks a message to her mother who is very proud. Lila thanks Delcatty and congratulates Dawn. Raoul Contesta then awards Dawn the Celestic Ribbon. Lila goes up to Delcatty and comforts him about the loss, and then she sees the big smile on Dawns face as Dawn hugs Ambipom excitedly.
Later, to celebrate Dawn's victory, Lila lets the gang pick out whatever they like from her shop. All of them, including their Pokémon, try out a lot of clothes, (for Ash, Brock, and Dawn), and jewelry for the Pokémon, before thanking Lila. Lila also thanks Dawn for letting her experience excitement she has not felt in a long time. Ash also reveals that their battle helped him come up with a way to counter Fantina's Hypnosis.