The film delves deep into the lives of the Irish-Catholic Fitzpatrick brothers, Mickey (Edward Burns) and Francis (Mike McGlone), exploring the tangled web of love, loyalty, and betrayal that defines their relationships. Mickey, a blue-collared taxi driver from New York City, grapples with the emotional fallout from the infidelity of his ex-fiancée, Heather (Cameron Diaz). On the other hand, Francis, a white-collared stock investor navigating the chaotic world of Wall Street, struggles to balance his dishonesty toward his wife, Renee (Jennifer Aniston), with the burgeoning affair he maintains with Heather.
Every weekend, Mickey and Francis try to reconnect with their family, making the trek to their parents' home in Long Island. While their mother remains an unseen presence, the brothers often indulge in banter with their emotionally distant father, Frank (John Mahoney), an old-school figure with entrenched conservative views. Frank's advice, often misguided, encapsulates the essence of his belief: to "live life as you desire and pursue success relentlessly."
As fate would have it, during one of his cab rides, Mickey encounters Hope (Maxine Bahns), a vibrant NYU art student. Struck by her charm, he makes the impulsive decision to marry her just days after their meeting. When Mickey and Hope arrive at Francis and Renee's apartment to announce their whirlwind marriage, it creates a stir—especially since Francis is left feeling neglected and unimportant, as he wasn't asked to be the best man. Mickey’s excitement soon dims as the realities of his new life unfold, revealing stark contrasts between his conservative views and Hope's liberal, free-spirited lifestyle.
Similarly, Francis finds himself in a precarious position. Torn between two women—his wife Renee, who is increasingly concerned about their fading connection, and his mistress Heather—he frequently ponders his role as a married man. His indecision is only compounded by Renee's sister, Molly (Amanda Peet), who insinuates that Francis might be struggling with his sexuality.
The tension mounts when Frank learns that his wife hasn’t attended church in months, leading to discomfort in the family dynamics. Alongside this revelation, Mickey's encounter with Heather provides a turning point, as their contentious history re-emerges, stirring unresolved feelings. The familial rifts come to a head when both brothers confront each other about their respective entanglements, leading to a physical showdown orchestrated by their father. Mickey triumphs, but the victory brings little solace.
The fabric of Francis and Renee's marriage unravels further, culminating in Francis's decision to pursue a divorce to marry Heather. However, Mickey's shocking disclosure about Heather's past as a prostitute threatens to derail Francis’s plans, tossing their fragile relationships into turbulent waters. Despite Mickey's best intentions, he struggles with his own loyalty to Francis—caught between friendship and the stark truths he feels compelled to share.
Meanwhile, Mickey's connection with Hope deteriorates as she prepares to leave for Paris, creating a rift that becomes more pronounced when he learns of her past involving Connie (Leslie Mann). Their relationship hangs by a thread, jeopardized by uncertainties and unspoken truths.
As Francis is confronted with the reality of losing Heather to her wealthy older partner, Mickey faces an inner conflict of his own, leading to an emotional climax between familial love and romantic loyalty. When tragedy strikes and Frank reveals that his own wife has left him for another man, the brothers find solace in their shared experiences. They come to grips with the frailty of love, receiving a surprising lesson in honesty from their father.
In a poignant conclusion, the film captures the essence of brotherhood as Mickey, Francis, and Frank set out for one last fishing trip—a symbolic journey where they embrace the bonds that remain despite their romantic failures. As they prepare to set off, the unexpected arrival of Hope hints at the possibility of reconciliation, though Frank’s traditional views on women add an ironic twist to this emotional journey. Ultimately, the brothers learn what it truly means to stand by each other amidst the chaos of love and life.
