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Movies like The Private Lives of Pippa Lee (2009)

The best movies like The Private Lives of Pippa Lee (2009) are In the Land of Women (2007), He Said, She Said (1991) and Irreplaceable You (2018). If The Private Lives of Pippa Lee hooked you with its comedy and drama, these 30 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. In the Land of Women (2007)

    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.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

  2. He Said, She Said (1991)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

  3. Irreplaceable You (2018)

    A stunning cancer diagnosis spurs Abbie to seek a future girlfriend for fiancé and childhood sweetheart Sam, who's clueless when it comes to dating.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Worth the HypeMovies like this
  4. The Best You Can (2025)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

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  5. After Everything (2018)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  6. Love & Sex (2000)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  7. Enemies, a Love Story (1989)

    A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Popcorn FlickMovies like this
  8. The Invite (2026)

    Joe and Angela's marriage is on thin ice. When they invite their enigmatic upstairs neighbors for a dinner party, the night spirals into unexpected places. Have they reignited the spark or lit the match that burns it all down?

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Worth the HypeMovies like this
  9. How to Please a Woman (2022)

    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.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

    Popcorn FlickMovies like this
  10. Numb (2007)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

  11. The Good House (2021)

    When wry New England realtor Hildy Good rekindles a romance with her old high-school flame, Frank Getchell, it ignites long-buried emotions and family secrets that propel Hildy toward a reckoning with the one person she's been avoiding for decades: herself. Based on the best-selling novel by Ann Leary.

    Why it matches: Recommended by TMDB viewers · both romance & drama

    Popcorn FlickMovies like this
  12. Hello I Must Be Going (2012)

    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.

    Why it matches: Recommended by TMDB viewers · both drama & comedy

  13. Ode to Joy (2019)

    Charlie suffers from a serious disease that causes acute narcolepsy whenever he is happy. Although he develops a variety of techniques to deny himself pleasure and deal with his sleep issues, they’re put to the test when he falls in love.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Popcorn FlickMovies like this
  14. Friends with Kids (2012)

    In the wake of their friends' marriages and eventual offspring, longtime pals Julie and Jason decide to have a child together without becoming a couple. By becoming "time-share" parents, they reason, they can experience the joys of parenthood without significantly curbing their personal freedom. However, when Julie and Jason both become involved with others, they discover that they secretly harbor romantic feelings for each other.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

  15. Solitary Man (2009)

    A car magnate watches his personal and professional life hit the skids because of his business and romantic indiscretions.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

  16. Young People Fucking (2007)

    On a Tuesday night, five couples have separate sexual adventures. Matt and Kris, friends for years, want to have an only-once, no-strings good time. Abby and Andrew, married, celebrate his birthday, but it's marred by angst and miscommunication. Mia and Eric are exes, making sure they are over each other. Jaime and Ken work together and this is a first date. Inez and Gord invite his roommate, Dave, to join them. By the time each couple has gone through a prelude, foreplay, sex, an interlude, orgasm, and afterglow, they've answered basic questions: can sex be anonymous, are we bored, is our marriage really finished, does anyone tell the truth, and how do we make someone happy?

    Why it matches: Recommended by TMDB viewers · both comedy & drama

  17. Strictly Sexual (2008)

    Two successful women, sick and tired of dating and relationships, decide to keep two young men in their pool house for strictly sexual purposes.

    Why it matches: Recommended by TMDB viewers · both drama & comedy

    Popcorn FlickMovies like this
  18. Is This Thing On? (2025)

    As their marriage quietly unravels, Alex faces middle age and an impending divorce, seeking new purpose in the New York comedy scene while Tess confronts the sacrifices she made for their family—forcing them to navigate co-parenting, identity, and whether love can take a new form.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Popcorn FlickMovies like this
  19. Modern Romance (1981)

    A film editor breaks up with his girlfriend, unsure if he is in love.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Popcorn FlickMovies like this
  20. Walking and Talking (1996)

    Just as Amelia thinks she's over her anxiety and insecurity, her best friend announces her engagement, bringing her anxiety and insecurity right back.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Popcorn FlickMovies like this
  21. The Extremists' Opera (2016)

    The semi-biographical The Extremists' Opera follows the everyday and inner struggles of a women-only alternative theater group delivering explosive and politically controversial explosive stage performances under the control of tough mannered director Naoko.

    Why it matches: Similar story and style · both romance & drama

  22. The Beautiful Woman Without Mercy (1921)

    "Taking its title from John Keats’s early 19th-century poem, this highly personal melodrama finds Dulac interrogating the archetype of the femme fatale. La belle dame sans merci follows a famous actress who was once seduced and abandoned by a rich man and subsequently resolved to become a “merciless woman,” forever scheming to hurt others (men in particular) in a ruthless yet captivating manner. Dulac challenges the Romantic archetype embodied in Keats’s poem by way of symbolist mise en scène, self-reflexive narration, and her typically associative approach to editing, locating a modern ambiguity within the stereotypical figures of 19th-century art." - Film Society of Lincoln Center

    Why it matches: Similar story and style · both drama & romance

  23. Am I Beautiful? (1998)

    Between Munich and Seville, the destinies of sixteen characters intertwine and intersect, missing each other or colliding head-on. They are all, without knowing it, at a pivotal moment in their lives...

    Why it matches: Similar story and style · both comedy & drama

  24. Summertime (2015)

    In 1971, a young woman moves from the French countryside to Paris and begins a passionate love affair with a feminist leader.

    Why it matches: Similar story and style · both drama & romance

    Popcorn FlickMovies like this
  25. Annalyn (2012)

    Agnes is not satisfied with her life. She wants a change, but her relationship with her single parent father and dominant girlfriend inhibit her to do something about it. When the father introduces his new wife, Annalyn, everything changes. The same-aged Filipino stepmother helps Agnes see a new path. Soon emerges something that no one could have foreseen.

    Why it matches: Similar story and style · both drama & romance

  26. The Little Thief (1988)

    In a small town in post-WWII France, 16-year-old Janine tries to improve her conditions by any means necessary. Three people—Michel, a married lover; Raoul, a fellow thief; Mauricette, a photographer she meets in prison—will help her learn from her mistakes.

    Why it matches: Similar story and style · both romance & drama

    Popcorn FlickMovies like this
  27. Manivald (2018)

    Manivald is a fox in his early 30s. He is still living at home with his mother. One day a young hot wolf called Toomas comes to fix the washing machine. A love triangle develops between the three of them. Things get out of hand and Manivald realizes that it is time to move out.

    Why it matches: Similar story and style · both romance & comedy

  28. Grease 2 (1982)

    It's 1961, two years after the original Grease gang graduated, and there's a new crop of seniors and new members of the coolest cliques on campus, the Pink Ladies and T-Birds. Michael Carrington is the new kid in school - but he's been branded a brainiac. Can he fix up an old motorcycle, don a leather jacket, avoid a rumble with the leader of the T-Birds, and win the heart of Pink Lady Stephanie?

    Why it matches: Similar story and style · both comedy & romance

  29. 10 (1979)

    A Hollywood songwriter goes through a mid-life crisis and becomes infatuated with a sexy blonde newlywed.

    Why it matches: Similar story and style · both comedy & romance

  30. Fill Your Heart with French Fries (2016)

    'Fill your Heart with French Fries' is a sad comedy short - telling the tale of a young woman who gets dumped by her girlfriend at a fast food joint, and, too sad to leave, just stays there for a week.

    Why it matches: Similar story and style · both comedy & drama

Like The Private Lives of Pippa Lee and something else?

Blend two favourites and we’ll find the films in between.

Frequently asked questions

What are the best movies like The Private Lives of Pippa Lee?

The closest matches to The Private Lives of Pippa Lee are In the Land of Women (2007), He Said, She Said (1991) and Irreplaceable You (2018). Below are 27 more, each with the reason it matches.

What should I watch after The Private Lives of Pippa Lee?

Start with In the Land of Women (2007), the closest match to The Private Lives of Pippa Lee.

What is the highest-rated movie like The Private Lives of Pippa Lee?

The Invite (2026), rated 7.2/10 by 960 TMDB users.

What is the newest movie like The Private Lives of Pippa Lee?

The Invite (2026) is the most recent release on this list.

Are there English movies like The Private Lives of Pippa Lee?

Yes: In the Land of Women (2007), He Said, She Said (1991) and Irreplaceable You (2018).

How are movies similar to The Private Lives of Pippa Lee chosen?

First come films that Trakt’s viewers watch alongside The Private Lives of Pippa Lee, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.

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