Movies like Enemies, a Love Story (1989)
The best movies like Enemies, a Love Story (1989) are Sidewalks of New York (2001), Cyrus (2010) and Numb (2007). If Enemies, a Love Story 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 ratedBen-Hur (1959)7.9/10 from 3,343 votes
- NewestWhy Did I Get Married Again? (2026)Released 2026
Sidewalks of New York (2001)
The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives, the film weaves a humorous and biting commentary on the game of love -- easy to start, hard to finish.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisCyrus (2010)
With John's social life at a standstill and his ex-wife about to get remarried, a down on his luck divorcée finally meets the woman of his dreams, only to discover she has another man in her life - her son. Before long, the two are locked in a battle of wits for the woman they both love-and it appears only one man can be left standing when it's over.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisNumb (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
SnoozefestMovies like thisJack Goes Boating (2010)
A limo driver's blind date sparks a tale of love, betrayal, friendship and grace—centered on two working-class New York City couples.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisMumford (1999)
When a would-be psychologist, curiously named Dr. Mumford, comes to the idyllic town of the same name and offers his talent for listening and a disarming frankness, the town's quirkiest citizens scramble for a seat on his couch. As he lightens hearts darkened by old secrets no one realizes he's hiding a whopper of his own, or that he's fallen head over heels for one of his patients!
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisStrictly 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 thisBreaking & Exiting (2018)
Harry, a charming house thief, gets more than he bargains for during an attempted burglary when he stumbles upon Daisy and decides to save her from herself, sending both of them into a darkly comedic journey of self discovery and love.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisHow 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 thisThe 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
Worth the HypeMovies like thisXX/XY (2002)
Three friends begin a dangerous three-way relationship that spirals out of control, leading to dire consequences that haunt them ten years later.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisThe Giant Mechanical Man (2012)
An offbeat romantic comedy about a silver-painted street performer and the soft spoken zoo worker who falls for him.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisWhy Did I Get Married Again? (2026)
The couples reunite for the destination wedding of Marcus and Angela's daughter, bringing drama old and new as they ask, "Why did we get married again?"
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisNight Owls (2015)
After workaholic Kevin has a drunken one night stand with the beautiful train-wreck Madeline, he's horrified to discover that she's actually his boss' jilted ex-mistress. When she takes a bottle of sleeping pills, Kevin is forced to keep her awake... and over the course of the night the two begin to fall for each other.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisThe 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 thisDelirious (2007)
Les, a small-time celebrity photographer desperate to make it big, befriends Toby, a homeless young man with no direction except a vague desire to become an actor. When by chance, Toby becomes romantically involved with K'Harma Leeds, the hottest pop star of the moment, Les grows jealous and plots revenge.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisRosaline (2022)
Left heartbroken after Romeo begins to pursue her cousin Juliet, Rosaline schemes to foil the famous romance and win back her guy in this comedic twist of Shakespeare's Romeo and Juliet.
Why it matches: Recommended by TMDB viewers · both romance & drama
Worth the HypeMovies like thisDedication (2007)
A modern love story in which a misanthropic, emotionally complex author of a hit children's book is forced to team with a beautiful illustrator after his best friend and collaborator passes away. As Henry struggles with letting go of the ghosts of love and life, he discovers that sometimes you have to take a gamble at life to find love.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisLove Accidentally (2022)
Alexa and Jason are competing for a position at an advertising firm when their partners break up with them. Alexa mistakenly texts Jason, and they start a phone-only relationship. When they meet and the truth comes out, will true love prevail?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe Elder Son (2006)
A thief on the run convinces a single father that he is his long-lost son. Complications ensue when he falls in love with his newfound "sister".
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisCherry (2010)
Ivy League Freshman, Aaron Milton (17) gets a different kind of education when he falls for Linda (34) a vivacious former wild-child who has returned to college to straighten out her life. The curriculum gets more challenging when Aaron meets Linda's sarcastic 14 year-old daughter, Beth - who quickly develops a crush on him. The math doesn't work in either direction but the dysfunctional triangle becomes a learning experience for all involved.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisAnnie Hall (1977)
New York comedian Alvy Singer falls in love with the ditsy Annie Hall.
Why it matches: Similar story and style · both comedy & drama
Worth the HypeMovies like thisMeet the Fockers (2004)
Hard-to-crack ex-CIA man Jack Byrnes and his wife Dina head for the warmer climes of Florida to meet the parents of their son-in-law-to-be, Greg Focker. Unlike their happily matched offspring, the future in-laws find themselves in a situation of opposites that definitely do not attract.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisShabbat Dinner (2012)
Shabbat Dinner is boring as usual for William Shore. His mother has invited two crazy hippies and their son and is doing her best to show off, his father is drunk and berating their oddball guests, and he doesn't have much in common with their son Virgo. That is, until Virgo tells him that he has just come out as gay.
Why it matches: Similar story and style · both drama & romance
Jacob the Liar (1974)
A Jewish ghetto in the east of Europe, 1944. By coincidence, Jakob Heym eavesdrops on a German radio broadcast announcing the Soviet Army is making slow by steady progress towards central Europe. In order to keep his companion in misfortune, Mischa, from risking his life for a few potatoes, he tells him what he heard and announces that he is in possession of a radio - in the ghetto a crime punishable by death. It doesn't take long for word of Jakob's secret to spread - suddenly, there is new hope and something to live for - and so Jakob finds himself in the uncomforting position of having to come up with more and more stories.
Why it matches: Similar story and style · both drama & comedy
Aimée & Jaguar (1999)
In 1943, while the Allies are bombing Berlin and the Gestapo is purging the capital of Jews, a dangerous love affair blossoms between two women – one a Jewish member of the underground, the other an exemplar of Nazi motherhood.
Why it matches: Similar story and style · both drama & romance
Popcorn FlickMovies like thisLucky Number Slevin (2006)
Slevin is mistakenly put in the middle of a personal war between the city’s biggest criminal bosses. Under constant watch, Slevin must try not to get killed by an infamous assassin and come up with an idea of how to get out of his current dilemma.
Why it matches: Similar story and style · both drama
Worth the HypeMovies like thisThe Riot (1913)
When a girl delivering expensive garments loses them to some Irish shanty town kids, her boss, a Jewish clothier, is livid and a fight breaks out. Soon the melee spreads to the whole neighborhood with brick throwing merging into bomb throwing, with the sides on clearly ethnic lines.
Why it matches: Similar story and style · both comedy
The Promised Land (1975)
At the turn of the century, Lodz, Poland, was a quick-paced manufacturing center for textiles, replete with cutthroat industrialists and unsafe working conditions. Three young friends, a Pole, a Jew, and a German, pool their money together to build a factory.
Why it matches: Similar story and style · both drama
Worth the HypeMovies like thisWhere is the Truth? The Tragedy of the Jewish College Girl (1913)
The film is about a young Jewish student who has to work as a prostitute in order to maintain residence in Riga. This leads to a misunderstanding with tragic consequences.
Why it matches: Similar story and style · both drama
Ben-Hur (1959)
In ancient Judea, a Jewish aristocrat opposing Roman occupation of his homeland reunites with his childhood friend, now a Roman commander — setting in motion a saga of betrayal, adventure, tragedy, revenge, and faith.
Why it matches: Similar story and style · both drama
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Frequently asked questions
What are the best movies like Enemies, a Love Story?
The closest matches to Enemies, a Love Story are Sidewalks of New York (2001), Cyrus (2010) and Numb (2007). Below are 27 more, each with the reason it matches.
What should I watch after Enemies, a Love Story?
Start with Sidewalks of New York (2001), the closest match to Enemies, a Love Story.
What is the highest-rated movie like Enemies, a Love Story?
Ben-Hur (1959), rated 7.9/10 by 3,343 TMDB users.
What is the newest movie like Enemies, a Love Story?
Why Did I Get Married Again? (2026) is the most recent release on this list.
Are there English movies like Enemies, a Love Story?
Yes: Sidewalks of New York (2001), Cyrus (2010) and Numb (2007).
How are movies similar to Enemies, a Love Story chosen?
First come films that Trakt’s viewers watch alongside Enemies, a Love Story, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.