In Her Shoes
Maggie (Cameron Diaz) and Rose Feller (Toni Collette) are sisters with nothing in common but their shoe size. They were raised by their father Michael (Ken Howard) and stepmother (Candice Azzara) after their mother Caroline died in a car accident. Rose is the eldest; an ostensibly plain and serious lawyer who is protective of Maggie despite her flaws. Maggie is a free spirit who is unable to hold a steady job (due to her virtual inability to read) and turns to alcohol and men for emotional and financial support. Rose grudgingly allows Maggie to move in with her in her Rittenhouse Square apartment in Philadelphia when their stepmother throws her out of the house. Their already difficult relationship ends when Rose catches Maggie in bed with Jim (Richard Burgi), her boyfriend. Maggie subsequently disappears from Rose's life.
A few days before, while secretly looking through her father's desk for money, Maggie discovered a bundle of old greeting cards containing cash. She was astonished to discover that the cards were addressed to both her and Rose and were from their grandmother Ella (Shirley MacLaine). Now, homeless and without job prospects, Maggie travels to Florida to find her and hopefully a new source of income.
When Ella first hears from Maggie, she invites her to stay in her home, She admits to her close friend Ethel how Caroline was bipolar, and sent her a note several days before her death to look after her girls. So she letting Maggie stay with her partially out of guilt for abandoning her responsibilities as a grandmother. However, as time passes, Ella discovers that Maggie has come to do nothing but sunbathe and take money from her. Maggie asks Ella to finance an acting career for her; Ella agrees to match her salary dollar for dollar if she accepts a job with the assisted living section of her grandmother's retirement community. Meanwhile, Rose has decided to quit her job, become a dog-walker, and date Simon Stein (Mark Feuerstein) whom she had previously ignored. They become engaged.
Maggie befriends one of her patients, a blind retired professor of English literature (Norman Lloyd), who has asked Maggie to read works of poetry to him. She does so, but with great difficulty. After asking if she is dyslexic, the professor encourages Maggie to continue reading to him while offering emotional support to her. Maggie finds a friend in the professor, the first person in her life who does not ridicule her difficulties with reading (and actually helps her to improve in this area). As time passes with the professor, Maggie's confidence grows not only with reading but with her general image of herself. In addition, she also becomes friendly with the residents of the retirement community. In doing so, Maggie discovers a livelihood that is greatly needed among the elderly women: a personal clothing shopper, an activity for which Maggie shows enormous talent. Ella (who also does not ridicule her difficulties with math) offers to run the financial aspects of the business. In the process, they become close and resolve their history.
Meanwhile, Rose's reluctance to talk about Maggie is straining her relationships with those around her, such as Simon, her father, and stepmother. While Michael remains oblivious to his daughters' falling out and the stepmother does not care much of the sisters, Simon tries to get Rose to talk about Maggie. When he sees Rose and former boyfriend Jim converse about how Rose cannot talk about Maggie to anyone, Simon's patience has grown thin and effectively dumps Rose after she keeps protecting Maggie by staying silent.
Ella has also secretly contacted Rose and sends a plane ticket asking her to come for a visit. Rose is excited to hear from her long-lost grandmother, but her pleasure quickly sours when she arrives and discovers that her sister already lives there. After a long conversation with Ella, Rose reveals that after Caroline took Rose and Maggie on a spontaneous trip to New York (without Michael's knowledge), Michael and Caroline got into a huge argument, with Michael threatening to put her in a mental institution. Caroline killed herself 2 days later and sent a note to Ella, pleading with her to take care of her daughters. Maggie does not remember this as Rose shielded her from the events to protect her.
Ella never recovered from Caroline's death and never resolved her feelings towards Michael; for she felt he ignored the signs that his wife had problems. The three women bond and learn to resolve their complicated past. Meanwhile, Maggie has contacted Simon telling that Rose is in Florida and "in trouble" and arranges him to meet Rose at the elderly residents' party. The two rekindle their engagement after Rose finally opens up about Maggie's personality and Rose's desire to protect her fearing that Simon will come to hate Maggie.
Maggie decides to throw Rose's wedding, preparing the Jamaican/reggae theme in order to show Rose how much she loves her. At Rose's wedding, Ella also reconciles with Michael and Maggie reads a poem to Rose as a wedding gift.
dramatic, romantic, flashback