The film opens with a compelling voiceover from Jane Goodall, portrayed by Ashley Judd, as we are drawn into the intriguing world of animal behavior through a scientific experiment involving a bull and a herd of cows. The bull's peculiar habit of never mounting a cow more than once leads Jane to question if men operate in a similar manner, holding a preference for novelty over commitment. As she reflects on this, Jane invites us to journey back in time to discover the root of her beliefs.
At the heart of the narrative, Jane works as a production assistant on a talk show that has recently achieved syndication. The ambitious host, Dianne Roberts, played by Ellen Barkin, is driven by her relentless pursuit of high-profile guests, including the elusive Fidel Castro. Against this backdrop, we meet Eddie Alden, brought to life by Hugh Jackman, who serves as the show’s irrepressible producer. Eddie is notorious for his womanizing ways, which frustrate Jane who tries to address his behavior with good-natured critique. A comical twist ensues when Eddie seeks a roommate but finds his attempts thwarted by vengeful ex-girlfriends. When he jokingly suggests Jane move in with him, she vehemently declines.
The plot thickens with the arrival of Ray Brown, played by Greg Kinnear, the new producer, who instantly captivates Jane. Ecstatic about her feelings, she confides in her friend Liz, portrayed by Marisa Tomei, recounting her dismal luck with men. Meanwhile, Jane's sister is caught in the throes of a fertility program, adding another layer of complexity to her emotional landscape.
As their relationship blossoms, Jane and Ray enjoy a romantic evening filled with intimacy, culminating in a sweet kiss. The following day, Jane is on cloud nine, eagerly sharing the news with Liz, who advises her on navigating the complexities of dating Ray, especially with his girlfriend, Dee, lingering in the background. However, as their relationship progresses, tension begins to cloud the air. One fateful dinner, Ray delivers devastating news, breaking things off with Jane, leaving her heartbroken and filled with tears.
In an act of defiance and to reclaim her sense of self, Jane shocks everyone by announcing her decision to move in with Eddie. As she delves into the chaotic world of Eddie’s romantic escapades, she finds solace in their companionship over scotch and leftover Chinese food, realizing that their bond transcends mere friendship. During this time, Jane stumbles upon an article discussing the so-called "old cow syndrome" and feels inspired to explore her own theories about men's behavior.
Liz, working as a columnist for a men’s magazine, persuades Jane to pen her insights under the pseudonym Dr. Marie Charles. This column, addressing insecurities and dishonesty among men, quickly garners attention and becomes a massive success. However, the triumph is bittersweet as Jane wrestles with her emotions, especially when Ray reaches out during a Christmas party, expressing his desire to reunite.
At a pivotal New Year's Eve gathering, Jane is left devastated when Ray fails to show up. Emotional turmoil ensues as she desperately searches for Eddie, only to be met with disappointment. As Ray attempts to apologize later, Jane faces further complications when Dee unexpectedly appears, rekindling old wounds. During a board meeting, a vulnerable moment arises when Ray opens up about a film, prompting Jane to unleash her pent-up feelings regarding his emotional unavailability.
Meanwhile, Dianne, oblivious to the dynamics at play, advises Jane on winning back Ray’s affections, steering her into a labyrinth of advice that further complicates her situation. However, the turning point comes when Jane shares her fears regarding dating and relationships with Eddie, foreshadowing the fears that linger beneath her composure.
Tragedy strikes when Jane receives distressing news about her sister’s pregnancy, leading her to a profound realization about love and resilience. In a fit of courage, she leads a live interview on Dianne's show, revealing that the facade of Dr. Charles was merely a projection of her pain. “There is no Dr. Charles,” she states, underscoring the revelation that not all men are the same, and expressing her newfound belief that love can still flourish amidst heartache.
With Eddie's presence all but a memory, Jane races after him in a taxi, pouring her heart out and claiming her right to love again. Their passionate encounter closes the narrative, leaving viewers to reflect on the beautiful messiness of human relationships and the enduring quest for understanding in a world where love can heartlessly imitate the fickleness of a bull's affections.
