Stefani's opponent was a woman named Gaiane, who said she became a fan at 15 and has been to over 100 Stefani and No Doubt shows. Kimmel explained that Stefani and Gaiane would be quizzed on the minutiae of Stefani's life, and the winner would take home a personal belonging of their opponent. For Stefani, that was a jacket and bag from her sunglasses, while Gaiane was offering up her No Doubt vanity plate.
Stefani got off to a hot start, taking two of the first three questions, one about her aunt Donna's 90th birthday and another about the first album she ever purchased (Shaun Cassidy's self-titled debut). However, Gaiane mounted an impressive comeback, correctly naming the first song Stefani wrote ("Different People"), the character she played in The Aviator (Jean Harlow) and the company her dad worked for (Yamaha).
Stefani closed in on Gaiane's lead by naming the summer camp she attended as a child, but Gaiane was able to hoist her hero's bag and jacket after correctly naming the Prince song Stefani had featured on, "So Far, So Pleased."