Wobbuffet first belonged to trainer Benny before an accidental trade at a Johto Pokémon Swap Meet transferred it to Jessie. This occurred when Jessie's Lickitung was swapped via trade machine without her consent, leading Wobbuffet to join Team Rocket. Jessie initially disliked the trade due to Wobbuffet's lack of offensive moves.
The Pokémon frequently emerges unprompted from its Poké Ball, participating in Team Rocket's activities without direct orders. It regularly joins the Team Rocket motto recitation, positioning itself near Meowth. Wobbuffet punctuates group interactions with its vocalizations, especially following the team's defeats. Despite a stoic expression, it occasionally disobeys Jessie's battle commands if it identifies superior counterattacking strategies.
In combat, Wobbuffet relies solely on reflective moves like Counter and Mirror Coat, embodying its species' non-aggressive nature. This tactic succeeded against opponents including Chikorita and festival crashers at the Wobbuffet Festival. However, it fiercely defends its pitch-black tail if threatened, resorting to Destiny Bond. Loyalty drives protective actions, such as shielding Ash's Totodile from a Golem's attack and retrieving stolen mission items.
Regional journeys shaped Wobbuffet's experiences: In Hoenn, it wore a maid disguise to subdue a Claydol and participated in contests where its countering strategies sometimes caused Jessie's elimination. During Sinnoh missions, it aided Team Galactic in stealing the Adamant Orb and competed in the Wallace Cup's Performance Stage, wearing a specially designed necklace for a fashion show. Left at headquarters during Unova travels, Wobbuffet later rejoined Jessie in Kalos. There, it bonded with Dr. White's female Wobbuffet but chose loyalty to Jessie over staying with its mate.
Notable deviations include aiding a Kirlia against Team Rocket's capture plans and briefly reverting to Wynaut due to spacetime distortions from Dialga and Palkia, reversed after Arceus intervened. Beyond battles, Wobbuffet has demonstrated unexpected abilities like making Poké Puffs, driving vehicles, and wearing human disguises during operations.