Movies Like Sleepless in Madrid

If you liked Sleepless in Madrid (1998), a drama and comedy movie directed by Chus Gutiérrez, 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
You Will Meet a Tall Dark Stranger (2010)
★ 5.9/10Also comedy and drama
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…
2
A California Christmas: City Lights (2021)
★ 6.6/10Also romance and comedy
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.
3
L.A. Without a Map (1999)
★ 5.8/10Also drama and comedy
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…
4
Chéri (2009)
★ 6.1/10Also drama and comedy
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.
5
Madame (2017)
★ 5.9/10Also romance and comedy
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…
6
Not Easily Broken (2009)
★ 6.3/10Also drama and romance
A car accident and shifting affections test the bond between a married couple.
7
The Life List (2025)
★ 6.9/10Also romance and comedy
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.
8
Father of the Bride (2022)
★ 6.3/10Also romance and comedy
A father comes to grips with his daughter’s upcoming wedding through the prism of multiple relationships within a big, sprawling Cuban-American family.
9
Peace, Love & Misunderstanding (2011)
★ 5.8/10Also comedy and drama
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.
10
Chasing Papi (2003)
★ 6.7/10Also comedy and romance
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…
11
Love in Taipei (2023)
★ 6.8/10Also romance and comedy
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.
12
Bridget Jones: Mad About the Boy (2025)
★ 6.3/10Also romance and comedy
Bridget Jones navigates life as a widow and single mum with the help of her family, friends, and former lover, Daniel. Back to work and on the apps, she's pursued by a younger man and maybe – just maybe – her son's…
13
Which Brings Me to You (2023)
★ 6.3/10Also romance and comedy
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…
14
Nine Lives (2005)
★ 6.1/10Also drama and romance
Captives of the very relationships that define and sustain them, nine women resiliently meet the travails and disappointments of life.
15
Therapy Done Right (2026)
★ 7.6/10Also comedy and drama
A psychoanalyst who's lost faith in traditional therapy crosses every boundary to help a blocked novelist in this cutting Argentine dark comedy.
16
Fools Rush In (1997)
★ 6.5/10Also comedy and drama
After a one night stand with Alex, Isabel realizes that she is pregnant and they decide to get married. However, along with the marriage comes compromise of one's own cultural traditions.
17
The Heart Knows (2025)
★ 6.8/10Also romance and drama
After a heart transplant, Manuel feels a personality shift and explores his donor's life, leading him to meet the widowed Vale and her community.
18
200 Cigarettes (1999)
★ 5.8/10Also comedy and drama
In 1981 New York City, a collection of twentysomethings try to cope with relationships, loneliness, desire and their individual neuroses on New Years Eve.
19
Love Everlasting (2016)
★ 7.4/10Also romance and drama
Bridger is a young outsider who's always wanted more. He and his mother flee an abusive home, eventually finding a small town in the middle of nowhere. Once there, Bridger finds true acceptance with another misfit.
20
Coyote Ugly (2000)
★ 6.3/10Also comedy and drama
Graced with a velvet voice, 21-year-old Violet Sanford heads to New York to pursue her dream of becoming a songwriter only to find her aspirations sidelined by the accolades and notoriety she receives at her "day" job…