Penelope is a kindergarten teacher who brings wild Pokémon she's befriended into her classroom, giving her students hands-on experience with them. She appeared in the episode "Kindergarten Chaos!"
When Ash and his friends showed up at her school, Penelope challenged Ash to a battle on the spot—with the stakes being that he'd have to come with her if she lost. She used her Sylveon against his Froakie. The matchup looked competitive at first, but Sylveon's Attract move left Froakie infatuated and helpless, finishing things off with Draining Kiss. True to his word, Ash stuck around and let the kids interact with his Pokémon, encouraging his traveling companions to do the same.
Most of the children loved it. There was one exception, though—a kid named Randall who was too scared of Pokémon to participate because of something that had traumatized him in the past.
Things went south when Team Rocket showed up disguised as entertainers, snatched Pikachu and Sylveon, and peeled out in a truck. Randall and Froakie got grabbed too in the chaos. Ash managed to jump on and cling to the back of the vehicle, refusing to let them get away clean. Penelope realized Randall was missing and immediately took off after them with Serena, Clemont, and Bonnie; Fletchling ended up leading the group straight to Team Rocket's hideout. By the time they got there, Ash had already busted the stolen Pokémon out of their cages with help from Froakie and Randall, and sent Team Rocket packing with a blast-off.
Content compiled by AnimeList.moe from publicly available sources.