After her much older husband forces a move to a suburban retirement community, Pippa Lee engages in a period of reflection and finds herself heading toward a quiet nervous breakdown.
Pippa Lee feels dislocated when she and her husband Herb move from Manhattan to a retirement community. He's older than she, they have two children who are young adults, and the daughter hardly speaks to Pippa. Pippa tells us about her life, in long flashbacks, starting with her birth to a mom who was a social dynamo and addicted to pills. As a teen, Pippa moves out and lives a hippie life until meeting Herb, who was then married to a young siren. Pippa discloses tragedies and discoveries. In the present, she's sleepwalking at night and talking from time to time with a burned-out case, the 35-year-old son of a neighbor. Can Pippa connect?
At fifty, Pippa Lee positively glows with female serenity, the devoted wife of a brilliant publisher thirty years her senior, proud mother of successful twins and a lovely and adored friend and neighbor. But, when her husband spontaneously decides that they should leave New York for a retirement home as a "pre-emptive strike against decrepitude," and has an affair with someone even younger than she is, Pippa finds her beatific persona unraveling in alarming ways. The truth is, the gracious woman of the present day has seen more than her fair share of the wild side. She has finally found love and security in a family of her own. And now, that cozy world, too, is in danger.
- The plot revolves around Pippa's emotional issues that lead her toward an affair with Chris Nadeau (Keanu Reeves). Pippa and her husband Herb have sold their downtown apartment and moved to the suburbs. Their marriage has lost its spark and Herb is having heart problems.
In an interesting twist the plot flashes back to a younger Pippa played by Blake Lively, that gets spanked by a dominatrix named Kit (Julianne Moore). Pippa is involved in lesbian bondage films before having a torrid love affair with Herb, who helps her to get her life together.
There is also a rather dramatic flashback scene where Herb's wife at the time, Gigi Lee (Monica Bellucci), points a gun at Pippa, and then ends up committing suicide.
Pippa finally finds out that Herb is having an affair with a friend to the family, Sandra Dulles. Herb has a fatal heart attack and Pippa leave to explore her new relationship with Chris, leaving her children, Ben and Grace, to organize the funeral.