This episode opens up with the nearing end of a final Contest Battle between a young Johanna and another girl. 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 that that's 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.
The episode re-opens after the opening sequence showing a Pokémon Center, and it turns out this is a past memory of Johanna's that she was telling her daughter 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 the top 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 Wallace's Contest outfit. 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 Celestic Town Contest Hall Marian introduces the Contest, the Judges and shows off the Celestic Ribbon. In the changing rooms, as Dawn and her Buneary are struggling with Dawn's hair (yet again), 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 Appeals Round as Dawn watches from the waiting area. 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 Lila's making a comeback. Lila calls upon her Pokémon, and bursting from a Poké Ball with a Flora Seal is a Cherrim who opens up to reveal its Sunny form. Ash then scans it with his Pokédex. Lila begins her appeal 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 it 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 co. 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, most likely due to the unnecessary Fantina impression and the appeal identical to her previous one. 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 it avoids with Substitute. Delcatty wraps itself 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 it 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.
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 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.
- The song "Oración", music from Destiny Deoxys, Pokémon Ranger and the Temple of the Sea and The Rise of Darkrai are used as background music.
- Professor Oak's Pokémon lecture: Starly
- Jessie, disguised as Jessilina, dresses up like Fantina for this episode's Contest. She also uses a French accent similar to Fantina's.
- Dawn's appeal corresponds May's Appeal in Lessons In Lilycove as it was their third Contest and both had some type of unintentional effect in the appeal.
- James and Meowth wore the same outfits they wore in Gymbaliar!.
- This episode contains the anime's first representation of Substitute, an attack that has existed since Generation I.
- The dub title for this episode is a reference to the phrase "bridging the generation gap".
- Team Rocket doesn't blast off or recite their motto in this episode.
- In one scene, when Lila's bodyguard pulled her away, the ribbons on Dawn's dress disappear.
- At one point after Lila made her appeal Cherrim posed, the viewer can see a line running down its flower petal giving it the impression it has two flowers on its head instead of one.
- The status ailment Attraction does not wear off on its own in the games: the afflicted Pokémon must be switched out or the one who inflicted it must be removed from battle.