Movies Like The Private Lives of Pippa Lee
If you loved The Private Lives of Pippa Lee's Comedy and Drama storytelling, these films deliver a similar experience — carefully selected for tone, themes, and emotional depth. Each pick includes where to watch it right now.
★ Top Picks
Catch and Release
For a grieving fiancée, learning to love again requires the help of her late love's three best friends.
In the Land of Women
After a bad breakup with his girlfriend leaves him heartbroken, Carter Webb moves to Michigan to take care of his ailing grandmother. Once there, he gets mixed up in the lives of the mother and daughters who live across the street.
Griffin & Phoenix
A terminally ill man falls in love with a woman who has a secret that threatens their time spent together.
Spoiler Alert
Journalist Michael Ausiello embarks on a rollercoaster ride of emotions when Kit Cowan, his partner of 14 years, is diagnosed with terminal cancer.
Author! Author!
A broadway playwright is burning the candle at both ends. He is dealing with pressure from a production nearing premiere, a wife who is leaving him, and 5 children 4 of which belong to her.
After Everything
When Elliot, a brash 23-year-old living carefree in New York City, meets the sensible Mia and receives a damning diagnosis all in the same week, his world is turned completely upside down. But as their love blossoms amidst the chaos of his treatment, they discover that Elliot's illness is not the real test of their relationship – it's everything else.
You Will Meet a Tall Dark Stranger
Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with a call girl. His wife, Helena, reeling from abandonment, decides to follow the advice of a psychic. Sally, the daughter of Alfie and Helena, is unhappy in her marriage and develops a crush on her boss, while her husband, Roy, falls for a woman engaged to be married.
The Best You Can
Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, just as her world is turned upside down by the arrival of sharp but chronically underachieving security guard Stan Olszewski in this smart rom-com that reunites Bacon and Sedgwick on screen for the first time in 20 years.
More Movies Like The Private Lives of Pippa Lee
He Said, She Said
Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing their very different opinions alongside each other, which leads to a similarly combative local TV show. At the same time their initial indifference to each other looks like it may evolve into something more romantic.
Something's Gotta Give
When perpetually single, aging music industry exec Harry Sanborn, and his latest trophy girlfriend, Marin, arrive at her mother's beach house in the Hamptons, they find that her mother, playwright Erica Barry, also plans to stay for the weekend. Erica is scandalized by the relationship and Harry's sexist ways. But when Harry has a heart attack while there, and the doctor prescribes bedrest, his only option is to stay at the Barry home. Left in the care of Erica and his doctor, a love triangle starts to take shape.
Love & Sex
When her rather explicit copy is rejected, magazine journalist Kate is asked by her editor to come up with an article on loving relationships instead, and to do so by the end of the day. This gets Kate thinking back over her own various experiences, and to wondering if she is in much of a position to write on the subject.
How to Please a Woman
When her all-male house-cleaning business gets out of control, a mature woman must embrace her own sexuality, if she is to make a new life for herself.
In Good Company
Dan Foreman is a seasoned advertisement sales executive at a high-ranking publication when a corporate takeover results in him being placed under naive supervisor Carter Duryea, who is half his age. Matters are made worse when Dan's new supervisor becomes romantically involved with his daughter an 18 year-old college student Alex.
Numb
Hudson Milbank is a successful Hollywood screenwriter who suddenly and strangely finds himself without any emotional feelings. He tries doctor after doctor and shrink after shrink, but nothing works. The Golf Channel, lesbian exercise classes and a dizzying variety of pills get him through the day, but don't quite solve his problem. His writing partner tries everything to get him back to normal, but it's not until Hudson meets Sara that he finds a real motivation to get better and to actually start feeling again. From the writer of Deuce Bigalow, comes NUMB, a romantic comedy following an unusual man looking for strange love.
Sidewalks of New York
The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives, the film weaves a humorous and biting commentary on the game of love -- easy to start, hard to finish.
Hello I Must Be Going
An affair with a 19-year old actor helps reinvigorate life for thirty-something Amy after she moves home to her parents’ house following her divorce.
Another Year
During a year, a very content couple approaching retirement are visited by friends and family less happy with their lives.
Father of the Bride
A father comes to grips with his daughter’s upcoming wedding through the prism of multiple relationships within a big, sprawling Cuban-American family.
Tim
Handsome but backward gardener Tim Melville has a new woman in his life. She is Mary, his widowed employer, a woman who had given up on love until she had found Tim. At first they are friends. But soon they become lovers, as Mary, drawn to Tim's innocence and magnetism, begins to teach him all about life - and love.
Venus
Maurice is an aging veteran actor who becomes taken with Jessie, the grandniece of his closest friend. When Maurice tries to soften the petulant and provincial young girl with the benefit of his wisdom and London culture, their give-and-take surprises both Maurice and Jessie as they discover what they don't know about themselves.
Why These Movies Are Similar
These recommendations share core qualities with The Private Lives of Pippa Lee (2009): Comedy and Drama themes, similar narrative structure, and comparable emotional depth. NoBadPicks uses a combination of TMDB collaborative filtering, genre matching, and AI analysis to surface films most likely to resonate with fans of The Private Lives of Pippa Lee.
See full details for The Private Lives of Pippa Lee (2009)