Movies Like Painful Love

If you liked Painful Love (2020), a movie directed by Ricky Greenwood, 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
Your Friends & Neighbors (1998)
★ 5.8/10
Restless and unhappy, two couples get caught up in infidelity and deception. Barry is a sullen businessman married to Mary, a writer who is unsatisfied with their relationship. Mary begins an affair with Jerry, a smug…
2
Porno (2019)
★ 6/10
When a group of naive teens working at a movie theater in a small Christian town discover a mysterious film hidden in its basement, they unleash an alluring succubus who gives them a sex education…written in blood.
3
Boys Don't Cry (1999)
★ 7.4/10
A young transgender man explores his gender identity and searches for love in rural Nebraska.
4
King Cobra (2016)
★ 5.8/10
It’s 2006, YouTube is in its infancy, and internet porn is still behind a paywall. Taking the stage name Brent Corrigan, a fresh-faced, wannabe adult video performer is molded into a star by Stephen, a closeted gay…
5
Below Her Mouth (2017)
★ 6.8/10
An unexpected affair quickly escalates into a heart-stopping reality for two women whose passionate connection changes their lives forever.
6
Xiu Xiu: The Sent-Down Girl (1998)
★ 7.2/10
Young teen girl Xiu Xiu is sent away to a remote corner of the Sichuan steppes for manual labor in 1975 (sending young people to there was a part of Cultural Revolution in China). A year later, she agrees to go to even…
7
Unfaithful (2002)
★ 6.7/10
A New York suburban couple's marriage goes dangerously awry when the wife indulges in an adulterous fling.
8
In the Blood (2014)
★ 5.8/10
When her husband goes missing during their Caribbean vacation, a woman sets off on her own to take down the men she thinks are responsible.
9
Bob & Carol & Ted & Alice (1969)
★ 6.3/10
After returning to Los Angeles from a group therapy session, documentary filmmaker Bob Sanders and his wife, Carol, find themselves becoming vigilante couples counselors, offering unsolicited advice to their best…
10
Pimp (2018)
★ 6.2/10
An urban love story set on the hard streets of the Bronx. A struggling female pimp, named Wednesday, grows up learning the game from her dad. Once he's gone she's left to look out for her prostitute mother and…
11
Pretty Persuasion (2005)
★ 5.8/10
A 15-year-old girl incites chaos among her friends and a media frenzy when she accuses her drama teacher of sexual harassment.
12
Orgazmo (1998)
★ 6.1/10
A devout Mormon living in L.A. becomes a pornographic actor after his martial arts moves impress a big-time director.
13
Ricky Gervais: Mortality (2025)
★ 7/10
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
14
Bill Burr: Drop Dead Years (2025)
★ 7.2/10
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
15
Lockdown (2000)
★ 6.1/10
Avery (Jones) returns to college as a competitive swimmer after getting his life back on track. But his life takes another unexpected turn when he and his two friends (Bonds, Casseus) are wrongly accused of murder and…
16
The Overnight (2015)
★ 5.9/10
Alex, Emily, and their son, RJ, are new to Los Angeles. A chance meeting at the park introduces them to the mysterious Kurt, Charlotte, and Max. A family “playdate” becomes increasingly interesting as the night goes on.
17
The Duke of Burgundy (2015)
★ 6.3/10
Day in and day out, lovers Cynthia and Evelyn enact an elaborate sadomasochistic fantasy as mistress and maid. But as their ritual of domination and submission begins to turn stale, Cynthia yearns for something more…
18
Mammal (2016)
★ 6.3/10
After Margaret, a divorcée living in Dublin, loses her teenage son, she develops an unorthodox relationship with Joe, a homeless youth. Their tentative trust is threatened by his involvement with a violent gang and the…
19
Monster's Ball (2001)
★ 6.8/10
A prison guard begins a tentative romance with the unsuspecting widow of a man whose execution he presided over.
20
South Central (1992)
★ 6.7/10
During a 10-year sentence for murdering the leader of a rival South Central Los Angeles gang, Bobby Johnson finds religion and rehabilitation with the help of Muslim inmate Ali. Upon his release, Bobby returns home to…