Maggie, portrayed by Cameron Diaz, and her sister Rose Feller, brought to life by Toni Collette, lead vastly different lives yet share an unusual commonality—their shoe size. Raised in a household led by their father Michael (Ken Howard) and a stepmother (Candice Azzara) after the tragic loss of their mother in a car accident, their relationship is both fragile and complex. Rose, the older of the two, is a serious and somewhat plain lawyer who takes on the role of protector for her younger sister, despite Maggie's numerous shortcomings. In stark contrast, Maggie embodies a free-spirited and carefree lifestyle, one that is often hindered by her struggles with reading, as well as her reliance on alcohol and men for emotional stability and financial aid.
When Rose reluctantly invites Maggie to move into her apartment in the chic Rittenhouse Square area of Philadelphia, it’s only a matter of time before their already strained relationship hits an all-time low. This turning point occurs when Rose catches Maggie in a compromising situation with Jim (Richard Burgi), her boyfriend. Heartbroken and somewhat defeated, Maggie disappears from Rose's life entirely.
In a surprising twist, while surreptitiously rummaging through their father’s desk in search of a little extra cash, Maggie stumbles upon a collection of old greeting cards containing cash—cards generously sent by their grandmother, Ella (Shirley MacLaine), who has seemingly been looking out for her granddaughters all along. Faced with homelessness and nowhere to turn, Maggie takes a leap of faith and travels to Delray Beach, Florida, hoping to reconnect with Ella and possibly find a new avenue for financial support.
Upon her arrival and initial contact with Ella, Maggie is welcomed into her grandmother's home, partially motivated by Ella’s guilt over not having fulfilled her duties as a grandmother. However, it soon becomes clear that Maggie's intentions may not align with her grandmother’s hopes, as she settles in to sunbathe and eagerly accept money without any significant contributions. When Maggie expresses her ambition to pursue an acting career, Ella agrees to support her financially—under the condition that Maggie first commits to a job within the assisted living wing of her retirement community. Meanwhile, Rose embarks on a transformative journey of her own, leaving behind her law career to become a dog-walker and quietly nurturing a relationship with Simon Stein (Mark Feuerstein), ultimately leading to their engagement.
As Maggie begins to forge connections in the retirement community, she finds an unexpected ally in a blind, retired English literature professor (Norman Lloyd), who encourages her to read poetry to him. Despite her challenges with literacy, Maggie's friendship with the professor becomes a pivotal point in her life, offering her encouragement and support in ways she has never before experienced. With his guidance, she starts to overcome her reading difficulties, which also helps to bolster her self-esteem. Further deepening her involvement in the community, Maggie discovers a newfound vocation as a personal clothing shopper for the elderly residents, a role in which she excels. Ella gladly supports her efforts by managing the business side of things, allowing the two women to mend their past grievances and deepen their bond.
In a tangled web of family ties, Ella secretly reaches out to Rose, sending her a plane ticket for a visit. Full of anticipation for the chance to reconnect with her estranged grandmother, Rose's excitement quickly wanes upon realizing that Maggie is already in residence. Through heartfelt conversations with Ella, the sisters uncover the painful truth surrounding their mother’s tragic death—it was a suicide caused by her struggle with mental illness after refusing to take her medication. This revelation brings to light the unresolved tensions between Ella and her granddaughters, helping them to confront and heal from their complicated past.
Ultimately, the three women unite, coming together to foster a deeper understanding of one another. At Rose's wedding, the narrative culminates in a poignant moment of reconciliation, as Ella reconnects with Michael while Maggie gifts her sister a beautiful poem, encapsulating the work they've all done to mend relationships and find peace in their shared family legacy. Through the trials and tribulations of their individual journeys, they learn that love and understanding can indeed bridge even the deepest divides.
