As Gilly Noble (played by Chris Klein), known for his penchant for surprises, walks into the Shelbyville animal shelter with a stray cat named Ringo, he is blissfully unaware that his life is on the brink of a significant transformation. A fateful meeting with the aspiring hairstylist Jo Wingfield (portrayed by Heather Graham) leads to a haircut and an engaging conversation that ignites a spark between them. However, their blossoming romance takes a tumultuous twist when Jo accidentally nips off a part of Gilly's ear during the cut, prompting him to dash to the hospital for emergency surgery. In a bid to make amends, Jo extends an invitation for lunch the following day, where Gilly encounters her quirky mother, Valdine, and her ailing father, Walter.
Fast forward six months and an engagement later, Gilly's life is once again thrown into disarray when private detective Vic Vetter drops a shocking revelation: he is, in fact, Valdine and Walter's biological son. This startling news compels Gilly to reassess his relationship with Jo, ultimately leading the couple to part ways. As he grapples with this upheaval, Gilly faces the harsh reality of losing his job at the animal shelter, becoming the target of a smear campaign that unjustly labels him as a "sister-fucker."
Time continues to be unkind, and sixteen months later, yet another twist befalls the Wingfield family when Leon Pitofsky arrives, claiming to be Valdine and Walter's son, complete with a birth certificate. This revelation sends shockwaves through the family, reigniting resentment toward Gilly.
Meanwhile, Jo has moved forward in life, getting engaged to her ex-boyfriend Jack Mitchelson, a man known for his dubious reputation and manipulative tendencies. As she adjusts to this new chapter, Valdine pressures her daughter toward marriage, motivated by a desire to access Jack's wealth and influence. Unbeknownst to Jo, Gilly is still determined to clear his name and reclaim his place in her heart.
Amidst this turmoil, Gilly finds an unexpected friend in Dig, a courageous pilot who, despite having two prosthetic legs, offers steadfast support. As Gilly maneuvers through the challenging landscape that lies ahead, he must summon all his wit and resourcefulness to stay one step ahead of those intent on dragging him down.
However, as Jo embarks on a life entwined with Jack, the authorities descend upon their wedding with heartbreaking news: Gilly has tragically died in a car accident—a cruel revelation concocted by Leon, who is arrested for his involvement in the sabotage. The shocking betrayal leaves Jo devastated and prompts her to call off her engagement to Jack, leading to a fierce confrontation between Valdine and Leon that culminates in Valdine suffering a stroke, leaving her wheelchair-bound. It is further uncovered that Jack orchestrated the confusion surrounding Gilly’s parentage.
Just as the pieces begin to settle, Gilly resurfaces in Jo’s life at the animal shelter, where a misunderstanding leads him to believe that she is on the brink of self-harm. He rushes to her side, and they share a heartfelt reunion on the same rooftop where their connection first began.
In a breathtaking climax, Gilly and Jo tie the knot, celebrated by guests including Walter, now in good health, and Valdine, who adjusts to her new life with assistance. In a twist that adds further irony to their story, Vic Vetter makes a memorable entrance, revealing that they finally located their real mother, Suzanne Somers—a surprising twist that resonates deeply with Gilly, who once harbored a childhood crush on her.
