In Luxray Vision!, the group reused these guard outfits to remain undetected while they stole an Old Charm. While in the anime, the nature of Jessie's relationship with James is not explicitly stated, in the epilogue of the manga, James is shown confessing his love to Jessie. They are shown afterwards married with Jessie visibly pregnant. James posed as a proud father in the audience as Jessie, going by the pseudonym "Jessilynlyn", and Meowth competed in the Pokémon Ping Pong Tournament.

Despite her and James being major characters throughout the anime and manga, they have only appeared in the first Generation games. In Party Dancecapades!, Jessie and her team members decided to attend a dance party hosted by Monsieur Pierre. After seeing Serena and her friends go inside, Meowth noted that it would be a perfect chance to catch Pikachu. Jessie, however, decided to let go of these plans in favor of attending the dance party and decided on James being her date while Gourgeist decided Inkay to be hers. Later, she was seen flailing James during their dance. With the dance party over, Monsieur Pierre announced a Tag Battle and Miette and James were partnered against Ash and Serena. Despite James's chagrin, Jessie sternly told him to win the battle but he lost, leading to her and her Gourgeist eating from the table behind them out of frustration. In an attempt to steal Marilyn's Pokémon, Jessie posed as "Jessarilyn" alongside James's Mime Jr. The plan was thwarted after Marilyn refused the battle offer because Mime Jr. wasn't cute enough.Jessie bears a striking resemblance to Jessebelle and James' mother. This fact was commented on in "Holy Matrimony!" Jessie and James appeared in kimonos, with Jessie holding a goldfish in a bag while James had sweet treats in his hands. She also values her beauty and long hair; she will become furious if her face or her hair is damaged. A prime example is in Tracey Gets Bugged when a younger Scyther manages to slash her hair down to a shoulder-length, devastating her and sending her into a rage. Jessie also shows her violent outrage when someone insults her beauty by calling her old. Her anger also scares James and Meowth, especially when their missions end up in a failure.

Having stolen his Contest Pass and Ribbons, Jessie disguised herself as Anthony in an attempt to enter the Hoenn Grand Festival. The real Anthony and his Swalot later foiled her ploy as she was about to walk onto the stage. Jessie wore a Venomoth costume as a ploy to attract Bug Pokémon to her, while James and Meowth were armed with nets. They first appeared in costume as they flooded water into their pitfall trap with Ash and his friends trapped inside. She won at least two other showcases off screen, though the towns and methods are left undisclosed.Jessie and Meowth are also disappointed when James successfully catches Inkay by luring it in with food. Therefore, when she tripped into a wild Pumpkaboo, she decided to capture it. James, inspired from a phony Pokémon zodiac book given to them by a disguised Butch and Cassidy, dressed in a Moltres costume for the first time. After their cover was blown by Officer Jenny, Jessie and James posed as doctors, demanding that the beauty contestants hand over their Pokémon for a routine physical examination. Jessie wore a red dress for the Saffron City Contest. She wore this outfit again for the Chrysanthemum Island Contest in Spontaneous Combusken! and the Mulberry City Contest in New Plot, Odd Lot! Jessie, James, and Meowth wore Nurse Joy costumes as they sneaked into the Coumarine City Pokémon Center and kidnapped a wild Vanillite. This is notably the first time James has cross-dressed since Pokémon the Series: Diamond and Pearl.