Gail Daughtry and the Celebrity Sex Pass

Gail Daughtry, a hairdresser in small-town Kansas, and her fiancé, Tom, are two weeks away from their wedding when they discuss their "celebrity sex pass"—the one celebrity they could sleep with without violating their relationship. Tom initially chooses Tilda Swinton, and Gail chooses Jon Hamm, but after meeting Jennifer Aniston at a book signing, Tom changes his choice. When Gail catches the two together, she leaves with her friend Otto for a hairdressing convention in Los Angeles.

In Los Angeles, Gail accidentally swaps briefcases with Ludovica, a criminal plotting to destroy the world's financial system. Ludovica sends her henchmen, Sergio and Niccolo, to recover the case and kill Gail. After a psychic tells Gail the only way to repair her relationship with Tom is to fulfill her celebrity pass with Jon Hamm, she and Otto seek him out with the help of Caleb, an aspiring talent agent who loses his job at CAA after stealing Hamm's address.

Mistaking "Weird Al" Yankovic's home for Hamm's, the trio flees and joins forces with paparazzo Vincent and Hamm's Mad Men co-star John Slattery, who deduces that Hamm is staying at the Chateau Marmont. Hamm's security guard agrees to arrange a meeting if they can pitch him a movie. Meanwhile, Gail discovers the briefcase contains classified government documents that would make the perfect screenplay.

Sergio and Niccolo ambush the group, leading to a chase through the convention. Niccolo is killed while attempting to shoot Gail, and Gail and Otto are later kidnapped. Caleb, Vincent, and Slattery rescue them from an abandoned Western set, where Slattery dispatches Ludovica's remaining henchmen. Gail beats Ludovica to death before the group reaches Hamm's hotel to pitch their screenplay.

Although Hamm rejects the screenplay, he admires the group's determination, allows Vincent to photograph him, gets Caleb rehired, and gives Slattery a role in an upcoming film. He also honors Gail's celebrity pass, and the two sleep together. Despite their connection, Gail returns to Kansas intending to marry Tom.

At the wedding, Gail realizes she cannot go through with it. Jon Hamm arrives in a hot air balloon, declares his love to her, and proposes. Gail declines marriage, wanting to keep things casual after ending her long-term relationship. Jon agrees, and the two fly away together.