Ash and co. arrive in Veilstone City and meet Reggie, a breeder who happens to be none other than Paul's older brother. They also meet Maylene, the Veilstone Gym Leader who trains Fighting-type Pokémon, and her signature Pokémon, Lucario. Ash challenges her, but Maylene is too despondent to take challengers. She recently had a gym battle with Paul, who wiped the floor with her in no time and then belittled her skills. It turns out this is on top of more confidence issues she's been having since becoming the gym leader just six months prior. Knowing what Maylene is going through, Dawn decides to talk to her, while Ash and Brock get to know Reggie. Ash and Reggie have a best two out of three, which Ash wins (with Reggie offering to teach Ash's Staravia Brave Bird afterwards), and Maylene gets her confidence back. However, before Ash gets the chance to battle her, Dawn reveals that she has challenged Maylene herself!
This episode contains examples of the following tropes:
- Badass Normal: Maylene is capable of fighting her own Lucario, and even deflects a point-blank Aura Sphere barehanded.
- Break the Cutie: Maylene's bad loss to Paul followed by his cruel words sent her into a depression.
- Call-Back: Ash and Brock recognize the Aura Spheres coming from Lucario before they even see Lucario itself, and Team Rocket try to bribe Lucario to join Team Rocket by offering it some chocolate. Both are references to Lucario and the Mystery of Mew.
- Cast from Hit Points: This episode introduces the move Brave Bird, which, like Pikachu's Volt Tacle, hurts both the user and the target. Reggie offers to teach it to Staravia.
- Commonality Connection: Dawn and Maylene finds common ground in their struggles with self-confidence after experiencing recent losses. They're able to connect and build a bond over this shared experience.
- Continuity Nod: In this episode, Ash instantly recognizes what an Aura Sphere is despite it being his first time in Sinnoh. This makes the events of the movie Lucario and the Mystery of Mew canon to the anime.
- Curbstomp Battle: During Reggie's story, we see through flashback that Paul effortlessly kicked Maylene's ass in their gym battle. His Honchkrow, recently evolved from his Murkrow, beat Maylene's first two Pokémon, Meditite and Machoke, in no time flat, and then his Magmar, a Fire-type, easily beat Lucario, a Steel-type.
- Foreshadowing:
- Among all the badges and Battle Frontier Symbols Reggie won, one Symbol is missing.
- Reggie mentions he'd like to see a full battle between Ash and Paul.
- Heroic BSoD: Dawn and Maylene bonds over their shared self-confidence struggles following recent losses.
- Maylene has been in a severe depression since her crushing loss to Paul, along with his following "The Reason You Suck" Speech, which did not help her preexisting self-esteem issues as a new gym leader. It gets so bad that she has serious thoughts about quitting as the Veilstone Gym Leader, and her Lucario's harsh attempts to snap her out of the depression aren't doing much good either. Only when Dawn gently confides in Maylene her doubts concerning her career as a Coordinator, challenging her to a battle and watching Ash's battle with Reggie, does she start to believe in herself again.
- Dawn confides to Maylene that she is still in the middle of one herself due to her recent losing streak as a Coordinator, causing her to doubt that she has what it takes to make it as a Coordinator and worry if she's holding Ash from his dreams. This is likely the core reason for Dawn trying to help Maylene get out of her funk by requesting a battle with her: to make sure Ash gets his gym battle and, with luck, restore her confidence in the process as well.
- Jerkass: Paul is shown cruelly insulting Maylene, calling her weak after she loses to him very badly.
- Jerkass Has a Point: Disturbingly, Maylene seems to think he was right: she admits she was totally out of sync and that a Gym leader should act better. Of course, it's made clear it's her depression talking.
- Jerk with a Heart of Gold: Lucario's methods of convincing Maylene to remain a Gym Leader are pretty violent, but he only wants her to get out of her funk. He is seen genuinely smiling when she starts getting better.
- Kick the Dog: What does Paul say to Maylene after he whoops her ass in their gym battle? "You're the weakest leader I ever fought, and this lightweight badge is just like you."
- The Load: Dawn has a heart-to-heart conversation with Maylene about her worries that she might be wasting Ash's precious time by participating in Contests. She feels like she is not progressing and wasn't sure if it was worth Ash's time. Dawn requested a battle with her to help Maylene get out of her funk. It is hinted that Dawn's primary motivation is to ensure that Ash has his gym battle and, with a stroke of luck, restore her confidence in the process by demonstrating to herself that she can make a difference in Ash's dreams.
- Nice Guy: In contrast to his standoffish brother Paul, Reggie is very nice to Ash and treats his Pokémon quite well.
