Rose Feller (Toni Collete) has led a sensible life, but she has a wild side - it's in her closet. Her shoes, to be precise. Meanwhile, her sister Maggie (Cameron Diaz) is a bit less sensible, but she doesn't have quite the shoe collection of her sister. Oh, she'd like it, but she just doesn't have it. So when she's kicked out of her own apartment for coming home late one too many times (and too drunk), she goes to live with Rose.
The only problem is that she sleeps with Rose's boyfriend - and coworker - which means that Rose has had enough, too. That means that Maggie takes off for new digs, and that is when she finds out about a stack of letters that her grandmother sent her (and Rose) that her father and stepmother have kept hidden. So instead of going to New York like she had planned, she goes to Florida to visit her grandmother. Enter Ella (Shirley MacLaine).
She gives Maggie the direction she has been lacking, saying that if she earns some of her own money, she'll match it, enabling her to get on her feet again. Because that's what grandmothers do. But in the process, Maggie finds more than that - she finds a home, and finds a potential new career when some of the other women at the retirement home ask for help shopping, and she finds that she is really good at it.
In fact, Ella likes how things turn out so well, she tries to get Maggie to invite Rose down, but Maggie refuses, so Ella does it herself. Which comes at a perfect time, because Rose left the law firm after things soured with her boyfriend (the one who met Maggie, and is a partner), so she is now walking dogs. And another coworker, who really seems to like her, isn't working out at all.
But by the time she gets there, it is time for Maggie to do something for someone other than herself, so she gets Simon (the new guy) to come down and see Rose, and that's all it takes to get them back together and on the right track again.
Rated PG-13 for thematic material, language and some sexual content.
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