Movies Like Difficult Woman

If you liked Difficult Woman (2025), a drama and comedy movie directed by Summer Benowitz, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Lady Windermere's Fan (1925)
★ 6.9/10Also comedy and drama
A society woman believes her husband is having an affair, a misconception which may have dire personal consequences for all involved.
2
Landline (2017)
★ 6.2/10Also comedy and drama
A teenager living with her sister and parents in Manhattan during the 1990s discovers that her father is having an affair.
3
Hooking Up (2020)
★ 6.3/10Also comedy and drama
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…
4
CQ (2001)
★ 5.9/10Also comedy and drama
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…
5
SubUrbia (1997)
★ 6.2/10Also comedy and drama
A group of suburban teenagers try to support each other through the difficult task of becoming adults.
6
Don't Think Twice (2016)
★ 6.4/10Also comedy and drama
An improv group deals with several crises, including the loss of their lease and one member hitting the big time.
7
About Alex (2014)
★ 6.1/10Also comedy and drama
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…
8
My Own Love Song (2010)
★ 6.2/10Also comedy and drama
A wheelchair-bound singer and her best friend embark on a roadtrip to Memphis.
9
It Runs in the Family (2003)
★ 6/10Also comedy and drama
This is the story of a dysfunctional New York family, and their attempts to reconcile
10
Almost Friends (2017)
★ 6.3/10Also drama and comedy
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…
11
Treasure (2024)
★ 6.5/10Also drama and comedy
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.
12
Chloe and Theo (2015)
★ 5.9/10Also comedy and drama
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…
13
The House of Tomorrow (2019)
★ 6.8/10Also drama and comedy
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.
14
Family Weekend (2013)
★ 6.3/10Also comedy and drama
A 16-year-old girl takes her parents hostage after they miss her big jump-roping competition.
15
Madea Goes to Jail - The Play (2006)
★ 7.5/10Also comedy and drama
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…
16
Tyler Perry's Madea on the Run - The Play (2017)
★ 7.5/10Also comedy and drama
In trouble with the local authorities, Mabel Simmons, notoriously known as Madea, is on the run from the law. With no place to turn, she moves in with her friend Bam who is recovering from surgery. Unbeknownst to Bam…
17
Real Women Have Curves (2002)
★ 6.1/10Also comedy and drama
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…
18
On Becoming a Guinea Fowl (2024)
★ 7.5/10Also comedy and drama
On an empty road in the middle of the night, Shula stumbles across the body of her uncle. As funeral proceedings begin around them, she and her cousins bring to light the buried secrets of their middle-class Zambian…
19
Afterlife of the Party (2021)
★ 6.7/10Also comedy and drama
A social butterfly who dies during her birthday week is given a second chance to right her wrongs on Earth.
20
TalhotBlond (2012)
★ 6.3/10Also drama
Thomas Montgomery, a married father of two young daughters, gets seduced by the world of online gambling and chat rooms where a virtual romance and sexual obsession ultimately leads to the murder of an innocent man.