Movies like The Trouble with Romance (2007)
The best movies like The Trouble with Romance (2007) are Sidewalks of New York (2001), You Will Meet a Tall Dark Stranger (2010) and Camille (2008). If The Trouble with Romance hooked you with its comedy and drama, these 30 similar films are what to watch next, and every pick says why it matches.
The Trouble with Romance
Quick picks
- Highest ratedRosaline (2022)7.1/10 from 346 votes
- NewestThe Baltimorons (2025)Released 2025
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 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 thisCamille (2008)
A twisted honeymoon adventure about a young couple on their way to Niagara Falls.
Why it matches: Recommended by TMDB viewers · both comedy & drama
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 thisThe Baltimorons (2025)
A newly sober man's Christmas Eve dental emergency leads to an unexpected romance with his older dentist as they explore Baltimore together.
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 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 thisEnemies, a Love Story (1989)
A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies 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 thisIrreplaceable You (2018)
A stunning cancer diagnosis spurs Abbie to seek a future girlfriend for fiancé and childhood sweetheart Sam, who's clueless when it comes to dating.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies 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 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 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 thisHe Said, She Said (1991)
Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing their very different opinions alongside each other, which leads to a similarly combative local TV show. At the same time their initial indifference to each other looks like it may evolve into something more romantic.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisPeace, Love & Misunderstanding (2011)
A conservative lawyer named Diane takes her two teenage children Jake and Zoe to meet their estranged, hippie grandmother in Woodstock after her husband asks for a divorce.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies 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 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 thisA California Christmas (2020)
With his carefree lifestyle on the line, a wealthy charmer poses as a ranch hand to get a hardworking farmer to sell her family’s land before Christmas.
Why it matches: Recommended by TMDB viewers · both comedy & romance
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 thisChéri (2009)
The son of a courtesan retreats into a fantasy world after being forced to end his relationship with the older woman who educated him in the ways of love.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisBroken English (2007)
Nora Wilder is freaking out. Everyone around her is either in a relationship, married, or has children, while she's in her thirties, alone with job she's outgrown and a mother who constantly reminds her of it all. Not to mention her best friend Audrey's "perfect marriage". But after a series of disastrous dates, Nora unexpectedly meets Julien, a quirky Frenchman who opens her eyes to a lot more than love.
Why it matches: Similar story and style · both comedy & drama
SnoozefestMovies like thisMeet Bill (2007)
A mild-mannered bank executive mentors a teenage con artist and tries to make a career change as a doughnut merchant.
Why it matches: Similar story and style · both comedy & drama
Popcorn FlickMovies like thisWristcutters: A Love Story (2007)
Zia, distraught over breaking up with his girlfriend, decides to end it all. Unfortunately, he discovers that there is no real ending, only a run-down afterlife that is strikingly similar to his old one, just a bit worse. Discovering that his ex-girlfriend has also "offed" herself, he sets out on a road trip to find her.
Why it matches: Similar story and style · both comedy & drama
Worth the HypeMovies like thisThumbsucker (2005)
Justin Cobb, a teenager in suburban Oregon, copes with his thumb-sucking problem, romance, and his diagnosis with ADHD and subsequent experience using Ritalin.
Why it matches: Similar story and style · both comedy & drama
Popcorn FlickMovies like thisEverybody Wants to Be Italian (2007)
Are all relationships based on lies? Jake Bianski runs a fish market in north Boston, surrounded by Italians. For years, he's carried a torch for Isabella, an ex-girlfriend now married with three children and no interest in Jake. Yet, he tells everyone she's his girlfriend, including Marisa, a veterinarian his employees set him up with at the Italian singles club. She's interested in him until he tells her about his girlfriend, then he's persistent in asking her to be his friend. As the friendship bumps along, Jake realizes that reality may be better than fantasy, but what if Isabella changes her mind about Jake, and what if it comes out that Marisa, like Jake, isn't Italian?
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisThe Curiosity of Chance (2006)
It’s the ‘80s once again, new wave angst and genderbending fashion are all the rage, but new kid at school, Chance Marquis, is trying to find new ways to stand out. Being an odd and somewhat awkward teenager makes him the target of the school bully. To deal with this dilemma, Chance turns to the opposite ends of the high school spectrum for help. On one side is the flamboyant drag queen and at the other, the varsity jock, Levi Sparks with whom Chance develops a unique friendship.
Why it matches: Similar story and style · both comedy & drama
SnoozefestMovies like thisBarren Lives (1963)
A destitute family tries to escape the drought in the backlands of northeastern Brazil. Fabiano (Átila Iório), Sinhá Vitória (Maria Ribeiro), their two children and their dog Baleia wander aimlessly and almost hopelessly through the remote interior, surviving the forces of nature and the cruelty of men. An adaptation of the work by Graciliano Ramos.
Why it matches: Similar story and style · both drama
Worth the HypeMovies like thisToro Loco (2012)
Mateo, son of a notorious mob lord of the city, has been dumped by his wife who took his son away. He doesn't resist the shame and hires the most ruthless hit-man available to kill them. He hires Toro Loco, a cold, eccentric assassin with will bring the hell to this family, always under his own twisted rules.
Why it matches: Similar story and style · both comedy
Laws of Gravity (1992)
The lives of two incompetent young men from Brooklyn spin out of control after a friend returns from Florida with guns to sell.
Why it matches: Similar story and style · both drama
Secrets of a Soul (2012)
Secrets of a Soul: Margarethe, Creator of bizarre sculptures! Night club dancer? Mad woman? Victim of an occult conspiracy?! Dark menaces steal her soul and organs. Though dead they keep her alive...
Why it matches: Similar story and style · both drama
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Frequently asked questions
What are the best movies like The Trouble with Romance?
The closest matches to The Trouble with Romance are Sidewalks of New York (2001), You Will Meet a Tall Dark Stranger (2010) and Camille (2008). Below are 27 more, each with the reason it matches.
What should I watch after The Trouble with Romance?
Start with Sidewalks of New York (2001), the closest match to The Trouble with Romance.
What is the highest-rated movie like The Trouble with Romance?
Rosaline (2022), rated 7.1/10 by 346 TMDB users.
What is the newest movie like The Trouble with Romance?
The Baltimorons (2025) is the most recent release on this list.
Are there English movies like The Trouble with Romance?
Yes: Sidewalks of New York (2001), You Will Meet a Tall Dark Stranger (2010) and Camille (2008).
How are movies similar to The Trouble with Romance chosen?
First come films that Trakt’s viewers watch alongside The Trouble with Romance, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.