Pippa (Robin Wright Penn) is married to Herb (Alan Arkin), a successful publisher who is 30 years older. They have two grown children: Ben (Ryan McDonald), studying to be a lawyer, and Grace (Zoe Kazan), a photographic journalist. Pippa has relocated her ailing husband to a Connecticut retirement community after his three heart attacks but he insists on still working. After years of taking care of her children and now looking after Herb, Pippa has grown restless. She is experiencing something akin to a midlife crisis. At one point she says in a modest self-assessment: "To be perfectly honest, I've had enough of being an enigma. I want to be known." In flashbacks, part of the mystery of her life is revealed.

Pippa grows up as her mother Suky's (Maria Bello) prize possession. Her mother is a whirlwind of energy who also has wild mood swings. This is the consequence, teenage Pippa (Blake Lively) eventually learns, of her addiction to pills. Pippa as a result develops a keen sensitivity to what others are feeling.

When she realizes that she doesn't want to be dragged down by her mother, she leaves home and moves in for a wild stay with her aunt who is living with Kat (Julianne Moore), a lesbian who immediately connects with Pippa and wants to use her in a S&M film she is making. With little self-esteem and an addictive personality like her mother, Pippa spends years in chaos until she meets Herb, who is attracted to what he calls her "innate sweetness." Of course, no one before this has ever praised her inner qualities, and Pippa is drawn to this wealthy and handsome man who wants to marry her. Only trouble is that he's already married to a voluptuous socialite (Gigi Lee).

Back in the present time, with her husband facing deterioration (he calls it "being at the end of the line") and possible death, Pippa finds that her past keeps intruding on her shaky feelings about her own future. She proves to be a trusted advisor to Dot (Shirley Knight), a neighbor who is worried about her son Chris (Keanu Reeves) who is getting a divorce, and to Sandra (Winona Ryder) who is thinking of leaving her critical husband Sam (Mike Binder), a writer. When Pippa discovers through a video camera in her kitchen that she is sleepwalking, it comes as an outward sign of her inner confusion. Pippa is attracted to Chris, who after a divorce moves in with his parents and admits that his life is a mess. She senses that in some strange way they are soul mates.

The Private Lives of Pippa Lee is written and directed by Rebecca Miller (The Ballad of Jack & Rose) based on her novel. It is a quirky film that moves on an alternating current between heartbreak and humor. It is firmly anchored in Robin Wright Penn's Academy-Award caliber performance, which is filled with nuances and many magical moments of authentic connection with others. In one scene, for example, when Pippa identifies what makes Chris seem so odd to other people: "You can't lie." Or when she describes marriage as an arrangement in which love comes and goes. Or when her daughter volunteers to be her friend after years of chilliness between them. Or when she is seized by the realization that no one needs her anymore and she is free.

One of the qualities of the midlife crisis is the feeling of being stuck, unable to move. When Pippa makes a move, it is very liberating both for her and for us!

Special features on the DVD include a commentary with Robin Wright and writer/director Rebecca Miller; and interviews with Robin Wright, Alan Arkin, and Blake Lively.