New to the vibrant streets of New York City, Barbara Novak (Renée Zellweger) arrives at Banner House with an ambitious mission: to unveil her new book, Down with Love. This revolutionary work aims to empower women by encouraging them to embrace freedom from romantic attachments and enjoy physical intimacy without commitment, all while replacing the need for a man with indulgences like chocolate. Her belief is that by following these principles, women will enhance their roles in both the workplace and society.
However, the executives at Banner House decline to back her groundbreaking book. Barbara’s editor, Vikki Hiller, devises a plan that requires Barbara to meet Catcher Block (Ewan McGregor), an acclaimed writer at Know and well-known as a “ladies' man.” Despite his charm, Catcher persistently avoids Barbara, leading her to confront him in frustration and ultimately walk out on their meetings.
In the backdrop, Catcher’s best friend and boss, Peter MacMannus, develops feelings for Vikki, yet their romance remains complicated. Caught in their own insecurities, neither Peter nor Vikki can muster the courage to be open about their feelings, with Peter harboring doubts about his own masculinity and Vikki questioning his affection.
As Barbara and Vikki work on promoting the book, their efforts go viral after landing Judy Garland to sing Down with Love on The Ed Sullivan Show. The book becomes a sensation, inspiring women to challenge their relationships with men. This success piques Catcher's interest, but the tables turn as Barbara now finds herself turning him down.
Tensions reach a climax when Barbara appears on a national television show discussing a chapter titled “The Worst Kind of Man,” using Catcher Block as an example. His ego bruised after a disastrous date, Catcher vows to prove that Barbara is just like every other woman, desiring what men seek.
In a clever ruse, he arranges a casual meet-up disguised as an astronaut named Major Zip Martin, and this persona captivates Barbara, who longs for the attention of a man who now appears oblivious to her identity. They embark on glamorous adventures around New York, with an underlying tension brewing between them. As Catcher begins to genuinely fall for Barbara, the deceit becomes increasingly difficult to maintain.
The revelation comes to a head at a party where Barbara recognizes the man she has grown fond of. She confronts him and reveals that she isn’t Barbara Novak, but rather Nancy Brown, a former secretary who had once turned down Catcher's advances. Her motivation was to stand out from his usual flings and to make him fall for her in a true, special way.
Their growing connection leads them to realize there are deeper feelings at play. However, before they can solidify their relationship, Catcher’s other romantic interests complicate matters, prompting Barbara to assert her independence by embracing her identity as a "down with love" girl. Meanwhile, Vikki and Peter's own relationship faces hurdles, with each realizing their dynamics mirror those of Barbara and Catcher.
In a bittersweet turn of events, both couples find themselves grappling with loneliness and disappointment as their respective pursuits of love seem futile. Catcher, heartbroken and inspired by Barbara’s impact on him, writes a new story titled “How Falling In Love With Barbara Novak Made Me A New Man”. This leads him back to her, where a genuine connection rekindles amidst a transformative journey for both.
In the final moments, as Catcher departs Barbara's office, a twist unfolds when she surprises him on the elevator, revealing her newly dyed red hair – a sign she has bridged the gap between her two identities. Their journey culminates in a wedding in Las Vegas, fostering a new understanding of love that transcends traditional expectations, much like Vikki and Peter’s own eventual union. The credits roll with a shared song: Here’s To Love, encapsulating the essence of their journey together.
