Movies like Sleepless in Madrid (1998)
The best movies like Sleepless in Madrid (1998) are He Said, She Said (1991), A California Christmas: City Lights (2021) and You Will Meet a Tall Dark Stranger (2010). If Sleepless in Madrid hooked you with its drama and comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedCléo from 5 to 7 (1962)7.7/10 from 823 votes
- NewestTherapy Done Right (2026)Released 2026
- In SpanishTherapy Done Right (2026)Also in Spanish
He 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 thisA California Christmas: City Lights (2021)
Follows Callie and Joseph one year after they fell in love, now running a dairy farm and winery, but their romance is threatened when business and family obligations call Joseph back to the city.
Why it matches: Recommended by TMDB viewers · both romance & comedy
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 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 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 thisMadame (2017)
Anne and Bob, a well-to-do American couple, have just moved to a beautiful manor house in romantic Paris. To impress their sophisticated friends, they decide to host a lavish dinner party, but must disguise their maid as a noblewoman to even out the number of guests. When the maid runs off with a wealthy guest, Anne must chase her around Paris to thwart the joyous and unexpected love affair.
Why it matches: Recommended by TMDB viewers · both romance & comedy
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 thisI Met a Girl (2020)
An aspiring musician struggling with schizophrenia falls for a mysterious woman who may be all in his head. When she suddenly vanishes, he takes off on a cross-country journey across Australia to find her, forcing his long-suffering brother to chase after him.
Why it matches: Recommended by TMDB viewers · both romance & drama
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 thisThe Life List (2025)
When her mother sends her on a quest to complete a teenage bucket list, a young woman uncovers family secrets, finds romance — and rediscovers herself.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisLove in Taipei (2023)
A young American woman is sent by her parents to a cultural immersion program in Taipei where she begins a new journey of self-discovery and romance.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisWhich Brings Me to You (2023)
Two romantic burnouts, Jane and Will, are immediately drawn to each other at a mutual friend’s wedding. After a disastrous hookup in the coatroom, the two spend the next 24 hours together, trading candid confessions of messy histories and heartbreak, on the off chance that this fling might be the real thing.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisFather of the Bride (2022)
A father comes to grips with his daughter’s upcoming wedding through the prism of multiple relationships within a big, sprawling Cuban-American family.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies 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 thisNine Lives (2005)
Captives of the very relationships that define and sustain them, nine women resiliently meet the travails and disappointments of life.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisChasing Papi (2003)
Playboy Thomas Fuentes has so far been able to skate by in life on good looks and charm alone. But when his duplicitous relationships with three women -- impassioned waitress Cici, meticulous lawyer Lorena and bored socialite Patricia -- spiral out of control, he suffers a mental breakdown. His doctor recommends that he choose just one girlfriend -- but can he choose in time before they discover his deception?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisNot Easily Broken (2009)
A car accident and shifting affections test the bond between a married couple.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisDisappearing Acts (2000)
A struggling construction worker and an aspiring musician find themselves falling in love.
Why it matches: Recommended by TMDB viewers · both romance & drama
Popcorn FlickMovies like thisBlind (2017)
A novelist is blinded in a car crash that killed his wife and several years later rediscovers his passion for life and writing when he embarks on an affair with the neglected wife of an indicted businessman.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisTherapy Done Right (2026)
A psychoanalyst who's lost faith in traditional therapy crosses every boundary to help a blocked novelist in this cutting Argentine dark comedy.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisMonsoon Wedding (2001)
A stressed father, a bride-to-be with a secret, a smitten event planner, and relatives from around the world create much ado about the preparations for an arranged marriage in India.
Why it matches: Similar story and style · both comedy & drama
Popcorn FlickMovies like thisBend It Like Beckham (2002)
Jess Bhamra, the daughter of a strict Indian couple in London, is not permitted to play organized soccer, even though she is 18. When Jess is playing for fun one day, her impressive skills are seen by Jules Paxton, who then convinces Jess to play for her semi-pro team. Jess uses elaborate excuses to hide her matches from her family while also dealing with her romantic feelings for her coach, Joe.
Why it matches: Similar story and style · both comedy & drama
Popcorn FlickMovies like this36 Fillette (1988)
A 14-year-old pursues romance with a man while vacationing with her family in Switzerland.
Why it matches: Similar story and style · both drama & romance
SnoozefestMovies like thisBalcony (2013)
Jeton, a 10-year-old boy is sitting on the edge of a balcony on the 4th floor. Neighbours and passers-by, terrified by this situation, call the police and firefighters for help. But the situation quickly becomes unmanageable.
Why it matches: Similar story and style · both drama & comedy
FC Venus (2006)
Anna is persuaded by her boyfriend Paul to move from Berlin to his home town of Imma. What the notorious soccer hater doesn't know, however, is that joining his best friend Steffen's law firm is just a pretext. In reality, Paul and his buddies are there to save the soccer club he co-founded, Eintracht Imma 95, from relegation. Anna soon realizes that the players' wives have nothing to say to their soccer junkies: Artificial turf in the bedroom, Effenberg bedding and weekends on the soccer pitch. When she finds out the real reason for the move, she mobilizes her fellow sufferers to counter-attack after a fierce bout of frustration and challenges Paul and his friends to the ultimate duel on the soccer pitch. The bet is on: women against men. If the women win, soccer is over - and Paul has to go back to Berlin with Anna. Forever. If the men win, there will be no more complaining.
Why it matches: Similar story and style · both comedy & romance
Away from Her (2007)
Fiona and Grant have been married for nearly 50 years. They have to face the fact that Fiona’s absent-mindedness is a symptom of Alzheimer’s disease. She must go to a specialized nursing home, where she slowly forgets Grant and turns her affection to Aubrey, another patient in the home.
Why it matches: Similar story and style · both drama & romance
Worth the HypeMovies like thisAll for Love (2017)
When a romance novelist is teamed with a Navy SEAL as research for her book, by a mandate from her publisher, she is less than thrilled and he is more than honest. However, as she works with the SEAL, she has a change of heart and learns to look at her life and writing with a different point of view.
Why it matches: Similar story and style · both romance & comedy
Popcorn FlickMovies like thisThe Last Mistress (2007)
Secrets, rumors and betrayals surround the upcoming marriage between a young dissolute man and virtuous woman of the French aristocracy.
Why it matches: Similar story and style · both drama & romance
SnoozefestMovies like thisCléo from 5 to 7 (1962)
Agnès Varda eloquently captures Paris in the sixties with this real-time portrait of a singer set adrift in the city as she awaits test results of a biopsy. A chronicle of the minutes of one woman’s life, Cléo from 5 to 7 is a spirited mix of vivid vérité and melodrama, featuring a score by Michel Legrand and cameos by Jean-Luc Godard and Anna Karina.
Why it matches: Similar story and style · both drama
Worth the HypeMovies like thisOr (My Treasure) (2004)
Or shoulders a lot: she's 17 or 18, a student, works evenings at a restaurant, recycles cans and bottles for cash, and tries to keep her mother Ruthie from returning to streetwalking in Tel Aviv. Ruthie calls Or "my treasure," but Ruthie is a burden. She's just out of hospital, weak, and Or has found her a job as a house cleaner. The call of the quick money on the street is tough for Ruthie to ignore. Or's emotions roil further when the mother of the youth she's in love with comes to the flat to warn her off. With love fading and Ruthie perhaps beyond help, Or's choices narrow.
Why it matches: Similar story and style · both drama
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Frequently asked questions
What are the best movies like Sleepless in Madrid?
The closest matches to Sleepless in Madrid are He Said, She Said (1991), A California Christmas: City Lights (2021) and You Will Meet a Tall Dark Stranger (2010). Below are 27 more, each with the reason it matches.
What should I watch after Sleepless in Madrid?
Start with He Said, She Said (1991), the closest match to Sleepless in Madrid.
What is the highest-rated movie like Sleepless in Madrid?
Cléo from 5 to 7 (1962), rated 7.7/10 by 823 TMDB users.
What is the newest movie like Sleepless in Madrid?
Therapy Done Right (2026) is the most recent release on this list.
Are there Spanish movies like Sleepless in Madrid?
Yes: Therapy Done Right (2026).
How are movies similar to Sleepless in Madrid chosen?
First come films that Trakt’s viewers watch alongside Sleepless in Madrid, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.