Movies like Difficult Woman (2025)
The best movies like Difficult Woman (2025) are Lady Windermere's Fan (1925), Hooking Up (2020) and CQ (2001). If Difficult Woman hooked you with its drama and comedy, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest rated¿Y cómo es él? (2022)7.5/10 from 260 votes
- NewestTreasure (2024)Released 2024
Lady Windermere's Fan (1925)
A society woman believes her husband is having an affair, a misconception which may have dire personal consequences for all involved.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisHooking Up (2020)
Bailey and Darla embark upon a misguided and mutually deceitful form of therapy, one in which they must drive across the country, re-enacting Darla's colorful history as a sex addict. As their true motivations for the road trip come to light, the unlikely pair force one another to confront their issues, discovering that there might actually be more to love than just sex.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisCQ (2001)
A young filmmaker in 1960s Paris juggles directing a cheesy sci-fi debacle, directing his own personal art film, coping with his crumbling relationship with his girlfriend, and a new-found infatuation with the sci-fi film's starlet.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisAlmost Friends (2017)
A man in his mid-20s, still living at home with his mother and stepfather, puts all his eggs in one basket: the girl who works at his local coffee shop. The problem is, she has a serious boyfriend. As they become closer, the line between friendship and intimacy is blurred, and the situation forces both to examine where they are in their lives.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisAbout Alex (2014)
When a group of old college friends reunite over a long weekend after one of them attempts suicide, old crushes and resentments shine light on their life decisions, and ultimately push friendships and relationships to the brink.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisDon't Think Twice (2016)
An improv group deals with several crises, including the loss of their lease and one member hitting the big time.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisLandline (2017)
A teenager living with her sister and parents in Manhattan during the 1990s discovers that her father is having an affair.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisIt Runs in the Family (2003)
This is the story of a dysfunctional New York family, and their attempts to reconcile
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisTreasure (2024)
A music journalist accompanies her father, a charmingly stubborn Holocaust survivor, on a journey to his homeland. While she's eager to make sense of her family's past, her dad has an agenda of his own.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisChloe and Theo (2015)
A young woman, Chloe, living by her wits on the streets of New York City, has a chance meeting with a wise Inuit Eskimo, Theo, who was sent to New York by his elders to provide a message to the people of the world – We either change our destructive was or be destroyed by them. Chloe, who has been searching for something to believe in, becomes inspired by Theo and , with the help of a kind lawyer, Monica, the three of them present Theo’s story to the United Nations in hopes of creating a better future for all of us.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisBasically (2014)
A bright but acid-tongued young actress walks the viewer through the drudgeries of her privileged life in a series of clinical tableaux.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisJo Jo Dancer, Your Life Is Calling (1986)
Although Jo Jo Dancer has achieved success as a stand-up comedian, he hasn't found happiness. After receiving severe burns in a narcotics-related incident, Jo Jo remains in a coma, and, while in this state, he looks back on his life. Drifting off into memories of his troubled childhood, Jo Jo revisits his youth, recalling his eventual rise to fame and the decadence that followed. As he considers his existence, he must decide if he wants to go on living or not.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisSubUrbia (1997)
A group of suburban teenagers try to support each other through the difficult task of becoming adults.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisMy Own Love Song (2010)
A wheelchair-bound singer and her best friend embark on a roadtrip to Memphis.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisMadea Goes to Jail - The Play (2006)
Madea returns in another hilarious story in which she gets sent to the big house. But regardless of the circumstances, she gives her trademark advice and wisdom to her friends and family as they learn the importance of letting go, moving on, and forgiveness.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisThe House of Tomorrow (2019)
The film tells futurist, architect, and inventor R. Buckminster Fuller's incredible story through two teens hoping to get laid, become punk gods, and survive high school.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like this¿Y cómo es él? (2022)
Thomas is a meek man on the verge of a nervous breakdown. Despite his situation he decides to fake a work trip to go to Vallarta to confront Jero, a taxi driver who is sleeping with his wife.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisJuniper (2021)
When a self-destructive teenager is suspended from school and asked to look after his feisty alcoholic grandmother as a punishment, the crazy time they spend together turns his life around.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisFamily Weekend (2013)
A 16-year-old girl takes her parents hostage after they miss her big jump-roping competition.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisReal Women Have Curves (2002)
In East Los Angeles, an 18-year-old struggles between her ambitions of going to college and the desires of her domineering mother for her to get married, have children, and oversee the small, rundown family-owned textile factory.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like this
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Frequently asked questions
What are the best movies like Difficult Woman?
The closest matches to Difficult Woman are Lady Windermere's Fan (1925), Hooking Up (2020) and CQ (2001). Below are 17 more, each with the reason it matches.
What should I watch after Difficult Woman?
Start with Lady Windermere's Fan (1925), the closest match to Difficult Woman.
What is the highest-rated movie like Difficult Woman?
¿Y cómo es él? (2022), rated 7.5/10 by 260 TMDB users.
What is the newest movie like Difficult Woman?
Treasure (2024) is the most recent release on this list.
Are there English movies like Difficult Woman?
Yes: Lady Windermere's Fan (1925), Hooking Up (2020) and CQ (2001).
How are movies similar to Difficult Woman chosen?
First come films that Trakt’s viewers watch alongside Difficult Woman, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.