Roderick Blank is enjoying life as a high-powered executive for the posh fast-food chain "Swallows," eagerly looking forward to marrying his stunning fiancée, Fiona Wormwood. However, his bachelor party takes an unexpected twist when he receives an email listing every woman he has ever slept with—101 names in total, with Fiona surprisingly positioned at number 29. He initially brushes it off as a prank by his friends, Zack and Lester, until he runs into Carlotta Valdez, the seductive stripper who holds the prominent spot at number 30.
As Roderick digs deeper into this puzzling situation, he uncovers that the list is not a mere joke; it's connected to a mysterious machine owned by the shadowy Agency. This strange device claims to foresee the future and comes with a warning from its creators—Alpha, Beta, and Fred—who urge Roderick to destroy the list for his own sake, cautioning that it could dismantle his life and relationships. Despite their warnings, Roderick becomes obsessed with crossing off every name, calling off his wedding, and indulging in a whirlwind of adventures with various women from his list.
While traversing this indulgent path, Roderick forms temporary bonds with several women, yet an unquenchable desire pushes him to continue his quest. His friends become increasingly alarmed by his deteriorating mental and emotional state, imploring him to discard the list and reassess his priorities.
Meanwhile, a cryptic entity known as "Death Nell" has begun to enact revenge on men who have mistreated women. This mercurial vigilante lures her targets into a false sense of security, leaving them in comatose states while spray-painting feminist poetry in their wake. As Roderick relentlessly pursues the completion of his list, he finds himself caught in a complex web of morality and intrigue, eventually confronting the underlying truths of his desires and the severe repercussions of his actions.
Just as the thrill from his latest conquests begins to fade, Roderick's life turns chaotic when he discovers his driver's license, inadvertently revealing the true identity of Gillian De Raisx. This stunning revelation sends his already fragile mental state spiraling as he realizes that Gillian is next on his list.
Faced with twenty names still to check off, Roderick decides to abandon his mission, redirecting his energy towards various hobbies to stave off temptation. Yet, fate intervenes when he suffers a bike accident, leading him to a group of innocent female students from a Catholic college who believe he has been "divinely sent" to them.
Roderick's willpower crumbles as he yields to their allure, hastily completing his list. However, upon reaching the final name, he uncovers a chilling truth: Death Nell is no ordinary being, and she may hold the key to his life and death.
With a looming sense of dread, Roderick attempts to escape his fate by isolating himself, ultimately seeking another Gillian De Raisx in Sydney, Australia. As the Agency closes in on Death Nell, he experiences a profound transformation, haunted by memories of his past indiscretions.
Filled with remorse and a desire for redemption, Roderick’s journey leads him to a fortuitous meeting with Gillian at a diner. They share food and heartfelt dialogue as Gillian unveils her painful past, marred by an abusive marriage that has left her feeling shattered and weary.
Deeply touched by her story, Roderick bonds with Gillian, and they decide on a drastic course—a sedative-laced night of reckoning. As they submit to the effects of the pills, they drift into a dreamlike slumber, producing a haunting conclusion marked by the words "The End."
In an astonishing twist, Roderick and Gillian awaken from their shared ordeal miraculously unscathed, their joined fate sealed. The Agency’s comatose victims awaken, and the poignant aftermath suggests that Roderick and Gillian’s love was always destined to flourish.
