Kay was a voice actress for the Pokémon Showboat, a traveling performance group where actors provided voices while their Pokémon performed on stage. Unlike her fellow performers, Kay and her Raichu had a genuinely rocky relationship—they were nervous around each other and clearly didn't click.
The tension between them came from their first meeting. When they'd just met, Raichu was so excited it jumped into Kay's arms, but then used Thunder Shock. Kay panicked and threw the Pokémon away, which terrified Raichu. From that point on, the two fed off each other's anxiety—Raichu could sense Kay was uncomfortable around it, so it stayed on edge too.
Things finally turned around during a Team Rocket encounter. As Raichu's voice actress, Kay managed to distract the villains long enough for Raichu to send them blasting off. That shared victory was enough to break the ice between them, and they finally built some actual trust.
Content compiled by AnimeList.moe from publicly available sources.