10 Romance Movies With Deep, Complex, Relationship Stories

Romantic relationships are among the deepest and most complex connections a person can engage in, and countless movies have explored the joy, passion, and heartache at the center of these dynamics. From the exhilarating beginnings of a new love affair to the devesting demise of a once-loving marriage, the greatest romance movies capture the good, the bad, and the ugly of trying to find love in an increasingly fractured and complicated world. These depictions become even more profound due to the incredible skills of talented writers, actors, and directors who bring these stories to life.

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A truly great romance movie has to include deep and complex characters whose love story feels real and believable. This can include the complexities of emotional baggage or conflicting life circumstances, as the conflict that romance conjures is prime material for effective and heartbreaking filmmaking. Some of the best directors of all time have gifted the world with deep and complex relationship stories, as audiences have repeatedly turned out since the birth of cinema to watch love, romance, and deep emotional connections play out on the big screen.

10 The Big Sick (2017)

Directed by Michael Showalter

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The romantic comedy The Big Sick deals with complex themes of clashing cultural expectations as the son of Pakistani immigrants enters a relationship with an American woman. While Kumail Nanjiani, playing a fictionalized version of himself, is expected to marry a fellow Pakistani as his parents present potential arranged marriage partners, this becomes increasingly complex as he connects with Emily Gardner (Zoe Kazan.) As a nuanced story of the challenges faced by second-generation immigrants, it’s no surprise this rom-com was so effective as it was based on fact and written by Nanjiani and his wife, Emily V. Gordon.

One of the most impressive aspects of The Big Sick was that, although cultural expectations drive much of the film’s conflict, no character is presented as the story’s villain. Instead, The Big Sick unpacks the difficulties of traversing complex relationships, and both Kumail and Emily’s parents are presented as understanding three-dimensional people. With strong supporting performances from Ray Romano, Holly Hunter, and Bo Burnham, The Big Sick is a modern rom-com that addresses the fraught complexities and subtle challenges of integrating different cultures.

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9/10 The Big Sick RRomanceComedyDrama

Written by Emily V. Gordon and Kumail Nanjiani, The Big Sick stars Nanjiani as a fictionalized version of himself whose budding relationship with a woman named Emily is tested by their cultural differences and Emily’s sudden and baffling illness. Gordon and Nanjiani based the film on their lives and relationship, and Zoe Kazan stars alongside Nanjiani as Emily. 

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*Availability in US Director Michael Showalter Release Date July 14, 2017 Studio(s) FilmNation Entertainment , Apatow Productions Distributor(s) Amazon Studios , Lionsgate Writers Emily V. Gordon , Kumail Nanjiani Cast Zoe Kazan , Ray Romano , Kumail Nanjiani , Holly Hunter , Adeel Akhtar Runtime 120 minutes Budget $5 million Expand

9 Blue Jay (2016)

Directed by Alex Lehmann

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The complexities of a first love whose memory lingers long past the relationship’s life span is explored in the Netflix romantic drama Blue Jay. With Mark Duplass and Sarah Paulson as former high school sweethearts who encounter each other once again when Duplass returns to his hometown, the careful interactions and knowing looks this couple give one another hint at a world of emotion behind each of their eyes. As a film whose power comes as much from what’s left unsaid as what’s being depicted, Blue Jay captured the heartbreak and longing of romantic reminiscences.

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With Paulson’s character already married, these former soul mates slowly share their unspoken feelings and regret. Shot in black and white with a minimalist cast of just Duplass, Paulson, and legendary character actor Clu Gulager, as a convenience store clerk who remembers the pair from their lovebird days and mistakingly believes they’ve been together the entire time, Blue Jay was a poignant pontification on the complexities of old lovers taking a trip down memory lane. With a powerful script and great performances, Blue Jay will tug at the heartstrings of any hopeless romantic.

8 Marriage Story (2019)

Directed by Noah Baumbach

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Although so many romance movies are about the excitement of couples coming together, just as effective can be depictions of romance falling apart. This was exactly what writer and director Noah Baumbach captured in his devastating divorce movie, Marriage Story. Starring Adam Driver and Scarlett Johansson as Charlie and Nicole Barber, Marriage Story starts with what is supposed to be an amicable separation that soon devolves into a devastating custody battle as hurt feelings and deep emotional pain overtook the characters’ once-loving understanding of each other.

Marriage and divorce have been consistent subjects in Baumbach’s work, as breakout success The Squid and the Whale showcased a marriage’s disintegration from the children’s perspective, while Marriage Story was much more romantic relationship-centric. With a powerful blend of comedy and deeply stirring drama, Marriage Story peeled back the emotional complexity of love falling apart and the legal questions that can overtake natural logic in the divorce process. Marriage Story is such an effective deconstruction of heartbreak because it keeps the focus firmly on the emotional weight of its story and the deep feelings behind each calculated decision.

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Marriage Story RDramaComedy

Directed by Noah Baumbach, Marriage Story follows Charlie and Nicole Barber, a theater director and his actress wife, through the dramatic disintegration of their marriage and subsequent divorce. Adam Driver and Scarlett Johansson star as Charlie and Nicole, with a further cast that includes Laura Dern, Alan Alda, and Ray Liotta. 

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*Availability in US Director Noah Baumbach Release Date December 6, 2019 Studio(s) Netflix Distributor(s) Netflix Writers Noah Baumbach Cast Ray Liotta , Merritt Wever , Kyle Bornheimer , Alan Alda , Mickey Sumner , Adam Driver , Mark O’Brien , Julie Hagerty , Scarlett Johansson , Laura Dern Runtime 136 minutes Budget $8.6 million Expand

7 La La Land (2016)

Directed by Damien Chazelle

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While Damien Chazelle’s La La Land paid homage to Hollywood musicals with incredible music and spectacular visuals, it also tells a deep and complex romantic story. With Emma Stone as the aspiring actress Mia Dolan and Ryan Gosling as the jazz musician Seb Wilder, La La Land captures the complexities of deeply ambitious and driven people trying to simultaneously carve out a lasting and fulfilling relationship. While Mia and Seb are able to connect over their shared dreams, the single-mindedness that achieving them requires marks their love story as a doomed endeavor.

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A main theme of La La Land is the battle between sacrifice and support that the pair must juggle as they work toward their overwhelmingly ambitious goals. While Mia and Seb long to let themselves be swept away by a whimsical world of musical romance, the reality at the heart of their story means they appear to have found the right relationship at the wrong time. These themes were compounded by the bittersweet ending of La La Land, which saw the couple’s paths diverge as they acknowledged that although they love one another deeply, sometimes the answer is to let go.

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8.1/10 La La Land PG-13DramaMusicalComedy

Written and directed by Damien Chazzelle, the romantic musical La La Land tells the story of Seb Wilder (Ryan Gosling) and Mia Dolan (Emma Stone), a jazz musician and an aspiring actress pursuing their respective dreams in Los Angeles. The pair meet and fall in love, sharing their passions and hopes with one another as they become closer. J.K. Simmons, John Legend, Rosemarie DeWitt, and Finn Wittrock appear in supporting roles.

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*Availability in US Director Damien Chazelle Release Date December 9, 2016 Studio(s) Lionsgate Distributor(s) Lionsgate Writers Damien Chazelle Cast Hemky Madera , meagen fay , J. K. Simmons , Sonoya Mizuno , Rosemarie DeWitt , John Legend , Ryan Gosling , Finn Wittrock , Ashley Caple , Josh Pence , Emma Stone , Jason Fuchs Runtime 128 Minutes Budget 30 million Expand

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6 Phantom Thread (2017)

Directed by Paul Thomas Anderson

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Phantom Thread darkly explores the connection between romance and creativity by addressing ideas around control, power dynamics, and obsession. From writer and director Paul Thomas Anderson, Phantom Thread starred Daniel Day-Lewis as the meticulous dressmaker Reynolds Woodcock and his relationship with Alma Elson (Vicky Krieps), a waitress and eventual muse to the famed fashion designer. As an obsessive perfectionist, the dark undercurrents of Phantom Thread saw Reynolds trying to shape Alma into his ideal version of her.

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This strange and toxic dichotomy between Reynolds and Alma led to a perverse power struggle between the pair and showcased a co-dependent and unhealthy relationship dynamic. As Reynolds’ romantic life has a direct effect on his artistic fulfillment, it is thrilling to witness how his complex relationship would influence and shape his professional achievements. As an unconventional romance movie, Phantom Thread hinted at the peculiar ways a romantic relationship can fracture the personalities of those within it.

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6/10 Phantom Thread RDramaHistory

Starring Daniel Day-Lewis in his final film role before his retirement from acting, Phantom Thread follows excentric London dressmaker Reynolds Woodcock who becomes infatuated with a young waitress named Alma and begins using her as his muse. Reynolds and Alma’s turbulent relationship is the main focus of the film. Vicky Krieps stars alongside Day-Lewis as Alma, and Lesley Manville stars as Cyril, Reynolds’s sister. 

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*Availability in US Director Paul Thomas Anderson Release Date December 25, 2017 Studio(s) Focus Features , Annapurna Pictures , Ghoulardi Film Company , Perfect World Pictures Distributor(s) Universal Pictures , Focus Features Writers Paul Thomas Anderson Cast Daniel Day-Lewis , Camilla Rutherford , Lesley Manville , Vicky Krieps Runtime 131 minutes Budget $35 million Expand

5 In the Mood For Love (2000)

Directed by Wong Kar-wai

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Complex emotions and a deep longing for intimacy categorized the cult classic romantic drama In the Mood for Love. Telling the story of a man and a woman whose two spouses are having an affair, In the Mood for Love showcases how their respective experiences of their partner’s infidelity led to them slowly developing feelings for one another. As the couple grapples with the pain of being cheated on, they form a close and complex connection that avoids the trappings of so many other romance movies based on similar premises.

With extraordinary performances from Maggie Cheung and Tony Leung, In the Mood for Love was a tragic and heartbreaking story of unrequited passion. As a profound reflection of fundamental feelings and the crippling weight of societal pressures and expectations, the way the characters walk the fine line between closeness and distance allows for worlds of emotion to be expressed with minimal words. In the Mood for Love addresses themes of love, desire, and restraint as it portrays the heartbreak behind missed opportunities and the feelings that are just too big ever truly to let out.

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In the Mood For Love PGDramaRomance

In 1960s British Hong Kong, journalist Chow Mo-wan and secretary Su Li-zhen find comfort in their shared loneliness after discovering their spouses’ infidelity. Their evolving relationship takes them on a poignant journey across time and distance, exploring the depths of unspoken desires and missed opportunities.

Director Kar-Wai Wong Release Date March 9, 2001 Distributor(s) USA Films Writers Kar-Wai Wong Cast Tony Leung Chiu-wai , Maggie Cheung , Siu Ping-Lam , Tung Cho ‘Joe’ Cheung , Rebecca Pan Runtime 98 Minutes Main Genre Drama Expand

4 Past Lives (2023)

Directed by Celine Song

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Set over 24 years, Past Lives explores the deeply complex romance of childhood friends who, due to geographical separation, are forced to grow apart despite a deep love for one another. While South Korean Nora Moon (Greta Lee) first left her home country at 12 years old as her parents moved to Canada, her childhood sweetheart Hae Sung (Teo Yoo) was left behind but never forgot about the girl he held a candle for. Once they finally reconnected in New York 24 years later, Nora was already married, and the pair confronted their dormant feelings for one another.

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As an autobiographical story based on writer and director Celine Song’s actual experiences, Past Lives is packed with nuanced observations on the human condition and the often heartbreaking what-if questions that make up a life. With a profoundly moving script that manages to depict grand, sweeping emotions through simple, compelling dialogue, Past Lives is an incredible directional debut from the playwright Song. As one of the most effective dramas of the 2020s, Past Lives’ mastery of subtle emotions made it a masterclass in depicting deep, complex relationships.

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8/10 Past Lives PG-13DramaRomance

In Past Lives, childhood sweethearts Na Young and Hae Sung lose contact when Na Young’s family moves abroad. Twelve years later, they reconnect through social media, but their lives have diverged. As they meet again, unresolved feelings surface, leading to poignant reflections on love, choices, and the complexities of relationships.

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*Availability in US Director Celine Song Release Date January 21, 2023 Writers Celine Song Cast Greta Lee , Teo Yoo , John Magaro Runtime 106 minutes Main Genre Drama Expand

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3 The Before Trilogy (1995 – 2013)

Directed by Richard Linklater

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Director Richard Linklater has tracked the complex romance of Jesse (Ethan Hawke) and Céline (Julie Delpy) across three movies, each released nine years apart. Before Sunrise showcased the young couple’s first encounter on a train from Budapest and their deeply romantic day and night talking and getting to know each other in Vienna. Before Sunset saw them reuniting in Paris. Lastly, Before Midnight saw the pair married with children and facing mature and complex marital difficulties while vacationing in Greece.

The Before films were powerful showcases of cinematic minimalism. They utilized long monologues and extended conversations to give audiences great insight into the psychology of their characters. The Before movies give the full spectrum of deep and fulfilling romance by focusing on the intricate details of relationship dynamics, falling in love, and the challenges of staying together.

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2 Her (2013)

Directed by Spike Jonze

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Spike Jonze’s Her reflects on the complex combination of romance and technology as Theodore Twombly (Joaquin Phoenix) carves out a romance with an artificial virtual assistant named Samantha (voiced by Scarlett Johansson.) This futuristic sci-fi concept depicts a society where AI is designed to adapt and evolve, and the lonely and introverted greeting card writer Theodore finds love and connection with a non-human entity. While this may sound like the stuff of fantasy, the recent advances in AI’s abilities in the real world signal it may not be so farfetched.

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The complexities of Theodore’s emotional connection are explored in Her, as their romance feels deep and real. By reflecting on the isolating nature of modernity, Her takes universal feelings and emotions and depicts them in a sci-fi setting that taps into mankind’s deepest desires and insecurities. As a tender and inquisitive work of art, Her is an original and heartbreaking story that captures its characters, both human and artificial, with depth and nuance.

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5/10 Her (2013) RDramaRomanceScience Fiction Where to Watch

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*Availability in US Director Spike Jonze Release Date January 10, 2014 Cast Joaquin Phoenix , Amy Adams , Scarlett Johansson , Rooney Mara Runtime 126 Mins

1 Eternal Sunshine Of The Spotless Mind (2004)

Directed by Michel Gondry

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While most romance movies showcase the actual experience of having a relationship, Eternal Sunshine of the Spotless Mind took things a step further by literally looking at the psychology behind a relationship. As a sci-fi romance set in a world where estranged couples could erase the memory of their former romance, Eternal Sunshine depicts a man undergoing memory erasure who is desperately trying to find a way to hang onto a lingering reminiscence of his once-loving relationship. Through a non-linear story, Eternal Sunshine explores the importance of fully experiencing heartbreak rather than burying feelings away or eliminating them all together.

With Jim Carrey and Kate Winslet as Joel Barish and Clementine Kruczynski, the two incredible performances at the heart of Eternal Sunshine made this one of the most deeply romantic movies ever made. From screenwriter Charlie Kaufman, Eternal Sunshine captures the way that memory interacts with love and pain, as well as the joy that this conjures. As both a touching look at the sentimental beauty and existential nightmare of giving oneself over to romance, Eternal Sunshine is a powerful showcase of a deep and complex relationship story.

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8.6/10 Eternal Sunshine of the Spotless Mind RRomance Sci-FiDrama

Jim Carrey and Kate Winslet star in Eternal Sunshine of the Spotless Mind as Joel Barish and Clementine Kruczynski, a couple who rediscover their love after erasing each other from their memories. The 2004 drama is written by Charlie Kaufman, directed by Michel Gondry, and includes Mark Ruffalo, Elijah Wood, Kirsten Dunst, and Tom Wilkinson in its cast.

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*Availability in US Director Michel Gondry Release Date March 19, 2004 Studio(s) Universal Pictures Distributor(s) Focus Features , Universal Pictures Writers Charlie Kaufman Cast Kate Winslet , Jim Carrey , Elijah Wood , Kirsten Dunst , Mark Ruffalo Runtime 108 minutes Budget $20 million Expand

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Category: Entertainment