Movies like Portrait of a Serial Monogamist (2016)
The best movies like Portrait of a Serial Monogamist (2016) are The Other Sister (1999), Father of the Bride (1950) and You Will Meet a Tall Dark Stranger (2010). If Portrait of a Serial Monogamist 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
- Highest ratedImagine Me & You (2006)7.6/10 from 1,153 votes
- NewestDandelion (2025)Released 2025
The Other Sister (1999)
A mentally challenged girl proves herself to be every bit as capable as her "perfect" sister when she moves into an apartment and begins going to college.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisFather of the Bride (1950)
Proud father Stanley Banks remembers the day his daughter, Kay, got married. Starting when she announces her engagement through to the wedding itself, we learn of all the surprises and disasters along the way.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisYou Will Meet a Tall Dark Stranger (2010)
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.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisThe Big Picture (1989)
Hollywood beckons for recent film school grad Nick Chapman, who is out to capitalize on the momentum from his national award-winning student film. Studio executive Allen Habel seduces Nick with a dream deal to make his first feature, but once production gets rolling, corporate reality begins to intervene: Nick is unable to control a series of compromises to his high-minded vision, and it's all he can do to maintain his integrity in the midst of filmmaking chaos.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisL.A. Without a Map (1999)
An aspiring Hollywood actress, on a visit to a charming North England town, has a brief fling with the town undertaker, who also writes obituaries for the local paper. Returning home, where she works as a waitress at a Japanese restaurant, she tells everyone about the handsome "writer" she met on her trip. Unfortunately, he decides to follow her back to Hollywood, setting up the expected light romantic comedy with asides as the newcomer gains experience about the goings on in Hollywood.
Why it matches: Recommended by TMDB viewers · both drama & comedy
SnoozefestMovies like thisHitch (2005)
Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques fail to work on Sara Melas, a tabloid reporter digging for dirt on Allegra Cole's love life. When Sara discovers Hitch's connection to Albert – now Allegra's boyfriend – it threatens to destroy both relationships.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisImagine Me & You (2006)
During her wedding ceremony, Rachel notices Luce in the audience and feels instantly drawn to her. The two women become close friends, and when Rachel learns that Luce is a lesbian, she realizes that despite her happy marriage to Heck, she is falling for Luce. As she questions her sexual orientation, Rachel must decide between her stable relationship with Heck and her exhilarating new romance with Luce.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Worth the HypeMovies like thisStargirl (2020)
An unassuming high schooler finds himself inexplicably drawn to the free-spirited new girl, whose unconventional ways change how they see themselves…and their world.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisPicture Perfect (1997)
A young advertising executive's life becomes increasingly complicated when, in order to impress her boss, she pretends to be engaged to a man she has just met.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisDating Amber (2020)
Eddie and Amber decide to stage a relationship in order to stop everyone speculating about their sexuality. Eddie is keen to follow his dad into the military, while Amber dreams of moving to the liberal hub of London. The plan seems solid, but as their arrangement begins to fall apart, Eddie’s denial gets deeper as Amber realizes that a perilous future awaits her best friend unless she intervenes.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisThe Nanny Diaries (2007)
A college graduate goes to work as a nanny for a rich New York family. Ensconced in their home, she has to juggle their dysfunction, a new romance, and the spoiled brat in her charge.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisI Can't Think Straight (2008)
Tala, a London-based Palestinian, is preparing for her elaborate Middle Eastern wedding when she meets Leyla, a young British Indian woman who is dating her best friend. Spirited Christian Tala and shy Muslim Leyla could not be more different from each other, but the attraction is immediate and goes deeper than friendship. But Tala is not ready to accept the implications of the choice her heart has made for her and escapes back to Jordan, while Leyla tries to move on with her new-found life, to the shock of her tradition-loving parents. As Tala's wedding day approaches, simmering tensions come to boiling point and the pressure mounts for Tala to be true to herself.
Why it matches: Recommended by TMDB viewers · both drama & romance
Worth the HypeMovies like thisA Perfect Ending (2012)
This intimate drama follows Rebecca, a woman who has kept her sexuality a secret from her friends but chooses to reveal it to a stranger. While Rebecca's revelations may not yield the results she expects, a perfect ending is still in reach.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisThe Prince & Me 4: The Elephant Adventure (2010)
One year after their royal wedding, King Edvard and Queen Paige of Denmark receive an invitation to attend the wedding of Princess Myra of Sangyoon. Upon their arrival, Paige finds Myra is unhappy with her arranged marriage to the brooding and sinister Kah and is secretly in love with a young elephant handler named Alu.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisMy Brilliant Career (1979)
A young woman who is determined to maintain her independence finds herself at odds with her family who wants her to tame her wild side and get married.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisThey Won't Believe Me (1947)
On trial for murdering his girlfriend, philandering stockbroker Larry Ballentine takes the stand to claim his innocence and describe the actual, but improbable sounding, sequence of events that led to her death.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisWatching the Detectives (2007)
Neil, a self-proclaimed film geek and owner of Gumshoe video, has always been content to live vicariously through his favorite films noir. But when he meets Violet, a real-life femme fatale, his mundane world gets turned upside down and the line between reality and the movies quickly begins to blur.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisPlatinum Blonde (1931)
Ann Schuyler is an upper-crust socialite who bullies her reporter husband into conforming to her highfalutin ways. The husband chafes at the confinement of high society, though, and yearns for a creative outlet. He decides to write a play and collaborates with a fellow reporter.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisDeparture (2016)
An English mother and her teenage son spend a week preparing the sale of their remote holiday house in the South of France. Fifteen-year-old Elliot struggles with his dawning sexuality and an increasing alienation from his mother, Beatrice. She in turn is confronted by the realisation that her marriage to his father, Philip, has grown loveless and the life she knows is coming to an end. When an enigmatic local teenager, Clément, quietly enters their lives, both mother and son are compelled to confront their desires and, finally, each other.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisWhat's Love Got to Do with It? (2023)
Two childhood friends now in their thirties must decide whether to follow their heads or their hearts once the man decides to follow his parents' advice and enter into an arranged marriage in Pakistan.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisRavenous (1999)
After arriving at his new, remote Army outpost, Capt. John Boyd and his regiment aid a wounded frontiersman who recounts a horrifying tale of a wagon train murdered by its supposed guide – a vicious U.S. Army colonel gone rogue. Fearing the worst, the regiment heads out into the wilderness to verify the gruesome claims.
Why it matches: Similar story and style · both comedy & drama
Popcorn FlickMovies like thisThe Sisterhood of the Traveling Pants 2 (2008)
Four young women continue the journey toward adulthood that began with "The Sisterhood of the Traveling Pants." Now three years later, these lifelong friends embark on separate paths for their first year of college and the summer beyond, but remain in touch by sharing their experiences with each other.
Why it matches: Similar story and style · both comedy & drama
Popcorn FlickMovies like thisThe Prince of Tides (1991)
A troubled Southern man talks to his suicidal sister's psychiatrist about their family history and falls in love with her (and New York City) in the process.
Why it matches: Similar story and style · both drama & romance
Popcorn FlickMovies like thisDandelion (2025)
In 1970s Los Angeles, rebellious queer teen Margaret gets thrown out of yet another foster placement and finds herself in the company of a mysterious social worker who's tasked with finding her a new home before the break of dawn. At odds and forced to travel the city together, Margaret realizes that running may not be her only option.
Why it matches: Similar story and style · both comedy & drama
Never Mind the Wall (2001)
Germany 1982: The country is divided into two parts. Nele, coming from West-Germany, travels to East-Germany where she meets Captain, singer of a band. They fall in love with each other, but the regime "takes care" of their relationship, meaning: They can not see each other again. Germany 1990: The country is reunited. Nele starts searching their lost love...
Why it matches: Similar story and style · both drama & romance
Detention 101 (2023)
Four adults are detained in their apartments with only each other and a computer for online company. They each come from a different class with differing views but they all have one defining purpose to understand why they are really being held hostage in their own homes. The AI refuses to reveal the reason.
Why it matches: Similar story and style · both comedy & drama
Raspberry Magic (2010)
An eleven-year-old science enthusiast turns her raspberry-growing project into an emotional mission to reunite her family after her father leaves and her mother falls into depression.
Why it matches: Similar story and style · both comedy & drama
Private Parts (1997)
The life and career of shock-jock superstar Howard Stern is recounted from his humble beginnings to his view from the top. Possessing a desire to be an on-air personality since childhood, Stern meanders through the radio world, always with his supportive wife, Alison, by his side. Landing a gig in Washington, D.C., Stern meets Robin Quivers, who will become his long-time partner in crime. When the two move to New York, they face the wrath of NBC executives.
Why it matches: Similar story and style · both comedy & drama
Popcorn FlickMovies like thisSticky Notes (2017)
The story of an emotionally detached backup dancer named Athena, who must return home to Florida to help care for her estranged father, Jack, after he gets diagnosed with cancer. There, she must contend with Jack’s irresponsible lifestyle, while looking after six year old Honey Bunny, who is only beginning to grasp the err in Jack’s ways.
Why it matches: Similar story and style · both comedy & drama
Buffy the Vampire Slayer (1992)
Blonde, bouncy Buffy is your typical high school cheerleader. But all that changes when a strange man informs her she's been chosen by fate to kill vampires.
Why it matches: Similar story and style · both comedy
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Frequently asked questions
What are the best movies like Portrait of a Serial Monogamist?
The closest matches to Portrait of a Serial Monogamist are The Other Sister (1999), Father of the Bride (1950) and You Will Meet a Tall Dark Stranger (2010). Below are 27 more, each with the reason it matches.
What should I watch after Portrait of a Serial Monogamist?
Start with The Other Sister (1999), the closest match to Portrait of a Serial Monogamist.
What is the highest-rated movie like Portrait of a Serial Monogamist?
Imagine Me & You (2006), rated 7.6/10 by 1,153 TMDB users.
What is the newest movie like Portrait of a Serial Monogamist?
Dandelion (2025) is the most recent release on this list.
Are there English movies like Portrait of a Serial Monogamist?
Yes: The Other Sister (1999), Father of the Bride (1950) and You Will Meet a Tall Dark Stranger (2010).
How are movies similar to Portrait of a Serial Monogamist chosen?
First come films that Trakt’s viewers watch alongside Portrait of a Serial Monogamist, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.