Romantic Movies With Characters That Needed To Go To Therapy

Olivia Hebert
Updated May 1, 2024 30 items

Have you ever watched a romantic movie and thought to yourself, “Hmm, maybe this person should try working on themselves instead of being in a relationship?” 

Oftentimes, the protagonists of our favorite big-screen romances are their own worst enemies, which is what makes them great characters, but not exactly the greatest partners. 

This thought might strike you as you watch Joseph Gordon Levitt's hopeless romantic Tom from (500) Days of Summer, who projects his romantic ideals onto a woman who doesn't want a relationship, and Hero Fiennes Tiffin's perpetually angsty Hardin from the After trilogy, the poster boy of toxic boyfriends. (Just dump him already, Tessa!) Perhaps after watching the classic My Best Friend's Wedding, you might realize that Julia Roberts' Jules may need some therapy as she desperately tries to sabotage said best friend's wedding.

Some characters don't need the neat happily ever after, they just need to do some inner work, so check out the following movies to find some movies with some protagonists who might need a little more character development. 

Rank which movies you think has the characters that need therapy the most!

  • Silver Linings Playbook
    1

    Silver Linings Playbook

    Bradley Cooper, Jennifer Lawrence, Robert De Niro
    28 votes
    Silver Linings Playbook is a captivating blend of drama and romance, presented by David O. Russell. The narrative revolves around Pat Solitano (Bradley Cooper), who finds himself back in his parents' home after a stint in a mental institution. He's determined to reconcile with his estranged wife, but destiny has other plans when he crosses paths with Tiffany Maxwell (Jennifer Lawrence). Their oddball friendship forms the heart of this movie which won Lawrence an Academy Award for Best Actress. Robert De Niro also shines as Pat's superstitious father. A tale of love, resilience, and second chances unfolds amidst the backdrop of Philadelphia's most vibrant neighborhoods.
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  • The Proposal
    2

    The Proposal

    Sandra Bullock, Ryan Reynolds, Mary Steenburgen
    7 votes
    Within the 2009 rom-com The Proposal, Margaret Tate (Sandra Bullock), an exacting book editor, finds herself in a pickle. Her work visa is denied, threatening her high-power job in New York. Andrew Paxton (Ryan Reynolds), her tormented assistant, becomes an unlikely solution. A faux engagement to circumvent immigration laws puts them in a hilarious situation. They journey to Alaska, meeting Andrew's vibrant family and experiencing eccentric local traditions. Amidst the comedy, unforeseen feelings emerge. Directed by Anne Fletcher, this film intertwines humor with unexpected romance, revealing that love can blossom in the most unusual circumstances.
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  • Crazy, Stupid, Love.
    3

    Crazy, Stupid, Love.

    Steve Carell, Ryan Gosling, Julianne Moore
    23 votes
    In the heartwarming film Crazy, Stupid, Love., life takes an unexpected turn for Cal Weaver (Steve Carell), a straight-laced husband and father. After his wife Emily (Julianne Moore) asks for a divorce, Cal finds himself thrust into the unfamiliar territory of singlehood. Enter Jacob Palmer (Ryan Gosling), a suave young man who takes Cal under his wing and teaches him how to navigate the dating scene. As Cal struggles to reinvent himself, he grapples with his feelings for Emily and a complex web of relationships unfolds. This romantic comedy-drama is defined by its charming performances and intricate plot twists, leaving audiences both entertained and intrigued.
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  • Friends with Benefits
    4

    Friends with Benefits

    Justin Timberlake, Mila Kunis, Patricia Clarkson
    27 votes
    Friends with Benefits is a modern romantic comedy that explores the fine line between friendship and romance. In this film, Jamie (Mila Kunis) and Dylan (Justin Timberlake), two disillusioned individuals, form an unlikely bond after meeting in New York City. They decide to add physical intimacy to their friendship without any emotional commitments. However, as they navigate through the complexities of their 'no strings attached' arrangement, things start to get complicated. The movie offers a humorous and insightful look into contemporary relationships, showcasing how love often finds a way despite our best efforts to keep it at bay.
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  • Twilight
    5

    Twilight

    Kristen Stewart, Robert Pattinson, Billy Burke
    21 votes
    Twilight, a captivating blend of romance and fantasy genres, introduces us to Bella Swan (Kristen Stewart), a high school student who relocates to the small, gloomy town of Forks. This seemingly mundane move sets the stage for a life-altering encounter with Edward Cullen (Robert Pattinson), her enigmatic classmate. Unbeknownst to Bella, Edward is a vampire, turning their budding romance into an enthralling saga of love and danger. As their relationship evolves, they're thrust into a world where vampires and humans coexist precariously, leading to an escalating series of events. The film's unique narrative earned it a nomination for Best Fantasy Film at the Saturn Awards.
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  • (500) Days of Summer
    6

    (500) Days of Summer

    Joseph Gordon-Levitt, Zooey Deschanel, Geoffrey Arend
    25 votes
    This indie rom-com follows the bittersweet relationship between Tom Hansen (Joseph Gordon-Levitt), an aspiring architect stuck in a mundane greeting card job, and Summer Finn (Zooey Deschanel), his charismatic colleague. Directed by Marc Webb, (500) Days of Summer subverts traditional narrative structure, unfolding in a non-linear fashion that mirrors Tom's emotional journey. Notably nominated for two Golden Globe awards, it explores themes of love, fate, and the nature of happiness through its protagonists' tumultuous romance and their contrasting views on relationships.
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  • Days of Being Wild
    7

    Days of Being Wild

    Maggie Cheung, Leslie Cheung, Andy Lau
    11 votes
    Days of Being Wild is a 1990 Hong Kong film directed by Wong Kar-wai. The film stars some of the best-known actors and actresses in Hong Kong, including Leslie Cheung, Andy Lau, Maggie Cheung, Carina Lau, Jacky Cheung and Tony Leung Chiu-Wai. Days of Being Wild also marks the first collaboration between Wong and cinematographer Christopher Doyle, with whom he has since made six more films. The movie forms the first part of an informal trilogy, together with In the Mood for Love and 2046.
  • The Kissing Booth
    8

    The Kissing Booth

    Joey King, Jacob Elordi, Molly Ringwald
    11 votes
    The Kissing Booth, a teen rom-com, traces the tumultuous love life of Elle Evans (Joey King). This high school junior's world spins as she violates her lifelong friendship rule - not to fall for her best friend Lee's (Joel Courtney) older brother, Noah Flynn (Jacob Elordi). An unexpected kiss at a school carnival booth unravels an intense romance between Elle and Noah. As their secret relationship grows, so does the tension with Lee. The film explores themes of friendship, loyalty, and love in this intricate adolescent triangle.
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  • After
    9

    After

    Josephine Langford, Hero Fiennes Tiffin, Pia Mia
    26 votes
    Tessa Young is a dedicated student, dutiful daughter and loyal girlfriend to her high school sweetheart. Entering her first semester of college, Tessa's guarded world opens up when she meets Hardin Scott, a mysterious and brooding rebel who makes her question all she thought she knew about herself -- and what she wants out of life.
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  • Punch-Drunk Love
    10

    Punch-Drunk Love

    Adam Sandler, Emily Watson, Philip Seymour Hoffman
    22 votes
    In the offbeat romantic comedy Punch-Drunk Love, Barry Egan (Adam Sandler), a small-business owner with seven sisters, leads an unremarkable life of loneliness. Unexpectedly, his world spins into chaos when he falls for Lena Leonard (Emily Watson). Concurrently, he becomes embroiled in a peculiar scheme involving pudding and frequent flyer miles. Directed by Paul Thomas Anderson, this film won the Best Director award at the 2002 Cannes Film Festival. A narrative that weaves love, anxiety and accidental crime together; it's an unusual tale that defies typical romance tropes.
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  • Eternal Sunshine of the Spotless Mind
    11

    Eternal Sunshine of the Spotless Mind

    Jim Carrey, Kate Winslet, Kirsten Dunst
    28 votes
    In the mind-bending drama Eternal Sunshine of the Spotless Mind, Joel Barish (Jim Carrey) finds his world turned upside down when he learns his ex-girlfriend, Clementine Kruczynski (Kate Winslet), has undergone a medical procedure to erase him from her memory. Struck by despair, he decides to do the same. The movie then takes us on an intricate journey through Joel's mind as his memories with Clementine progressively vanish. Renowned for its unique narrative structure and surreal visuals, this film won the Academy Award for Best Original Screenplay in 2005. A poignant exploration of love, loss, and memory, it remains a standout in director Michel Gondry's oeuvre.
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  • Love Actually
    12

    Love Actually

    Hugh Grant, Laura Linney, Colin Firth
    17 votes
    In the heartwarming film Love Actually, nine intertwined stories explore the complexities of love during the festive Christmas season. The ensemble cast includes characters like Prime Minister David (Hugh Grant), writer Jamie (Colin Firth), and aging rock star Billy Mack (Bill Nighy). Their tales of romance, heartbreak, and discovery unfold against a backdrop of London's charming streets and homes. Directed by Richard Curtis, this multi-narrative comedy-drama offers a humorous and touching exploration of love's many forms. Its deft storytelling and memorable performances earned it a BAFTA Award for Best Supporting Actor for Bill Nighy.
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  • Bridget Jones's Diary
    13

    Bridget Jones's Diary

    Renée Zellweger, Colin Firth, Hugh Grant
    15 votes
    In the heart of London, Bridget Jones (Renée Zellweger) is a thirty-something woman, grappling with her love life, career and self-image. She fills the pages of her diary with humorous observations and sincere confessions, in an attempt to navigate through life's complexities. When two men, Mark Darcy (Colin Firth) and Daniel Cleaver (Hugh Grant), enter Bridget's world, they introduce a whirlwind of romantic dilemmas. Bridget Jones's Diary is a witty romantic comedy that won Renée Zellweger an Academy Award nomination for Best Actress. The film is based on Helen Fielding's best-selling novel of the same name.
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  • My Best Friend's Wedding
    14

    My Best Friend's Wedding

    Julia Roberts, Dermot Mulroney, Cameron Diaz
    24 votes
    Julianne Potter, portrayed by Julia Roberts, finds herself in a precarious romantic predicament in the romantic comedy, My Best Friend's Wedding. When her long-time friend, Michael O'Neal (Dermot Mulroney), announces his engagement to the young and vivacious Kimmy Wallace (Cameron Diaz), Julianne realizes she harbors feelings for him. As the wedding looms closer, Julianne embarks on a comedic journey of self-discovery and unrequited love. Rupert Everett steals scenes as George Downes, Julianne's confidant, adding another layer of complexity to this tale of love and friendship. Directed by P.J. Hogan, this film offers an engaging exploration of relationships from an unconventional angle.
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  • Call Me by Your Name
    15

    Call Me by Your Name

    Armie Hammer, Timothée Chalamet, Michael Stuhlbarg
    22 votes
    In the sun-drenched Italian countryside, a profound encounter unfolds. Call Me by Your Name, a romantic drama, weaves the tale of Elio Perlman (Timothée Chalamet), a 17-year-old spending the summer in his family's villa. He crosses paths with Oliver (Armie Hammer), an American scholar visiting as his father's research assistant. As days pass, an intimate bond develops between them. The film, directed by Luca Guadagnino and based on André Aciman's novel, has garnered acclaim for its tender storytelling and evocative cinematography, earning four Academy Award nominations and winning Best Adapted Screenplay.
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  • Passengers
    16

    Passengers

    Jennifer Lawrence, Chris Pratt, Michael Sheen
    13 votes
    On a routine journey through space to a new home, two passengers, sleeping in suspended animation, are awakened 90 years too early when their ship malfunctions. As Jim and Aurora face living the rest of their lives on board, with every luxury they could ever ask for, they begin to fall for each other, unable to deny their intense attraction until they discover the ship is in grave danger. With the lives of 5,000 sleeping passengers at stake, only Jim and Aurora can save them all.
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  • He's Just Not That Into You
    17

    He's Just Not That Into You

    Ben Affleck, Jennifer Aniston, Drew Barrymore
    12 votes
    In the heart of bustling Baltimore, a group of friends navigate the complex terrain of modern relationships in He's Just Not That Into You. Gigi (Ginnifer Goodwin), a hopeful romantic, struggles to understand mixed signals from men. Her friend Janine (Jennifer Aniston) tries to save her marriage with Ben (Bradley Cooper), who's entangled with yoga instructor Anna (Scarlett Johansson). Meanwhile, Beth (Jennifer Connelly) seeks commitment from Neil (Ben Affleck), a firm non-believer in marriage. This ensemble romantic comedy explores love and heartbreak in the digital age, offering a humorous yet thoughtful look at how men and women often misunderstand each other.
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  • The Ugly Truth
    18

    The Ugly Truth

    Katherine Heigl, Gerard Butler, Eric Winter
    12 votes
    Abby Richter (Katherine Heigl) is a lovelorn TV producer who, despite a long and arduous search for the perfect mate, is hopelessly single. The battle of the sexes heats up when her employers team her up with Mike Chadway (Gerard Butler), an opinionated TV celebrity who plans to put Abby through the wringer to prove his own theories about what makes men and women tick.
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  • Overboard
    19

    Overboard

    Goldie Hawn, Kurt Russell, Edward Herrmann
    18 votes
    In the movie Overboard, a wealthy, spoiled heiress, Joanna (Goldie Hawn), hires a carpenter, Dean (Kurt Russell), for renovations on her luxury yacht. When she refuses to pay him for his work, their relationship turns sour. Fate intervenes as Joanna falls overboard and loses her memory. Dean, spotting an opportunity for payback, convinces her that they're married and living a life of humble means. As this farcical tale unfolds, Joanna adjusts to her new lifestyle while Dean grapples with the ethical implications of his actions. A romantic comedy sprinkled with elements of drama, Overboard explores themes of class disparity and personal transformation in a lighthearted yet thoughtful manner.
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  • 10 Things I Hate About You
    20

    10 Things I Hate About You

    Heath Ledger, Julia Stiles, Joseph Gordon-Levitt
    14 votes
    Welcome to 10 Things I Hate About You, a modern-day Shakespearean twist that dances on the line of teen romance and biting comedy. Set in an American high school, this late-90s gem revolves around two Stratford sisters: the rebellious Kat (Julia Stiles) and her popular younger sister, Bianca (Larisa Oleynik). When Cameron (Joseph Gordon-Levitt), a new student smitten by Bianca, learns of their father's strict dating rule, he hatches a plan involving bad boy Patrick Verona (Heath Ledger) to woo Kat. Amidst clever banter and unexpected romances, the characters navigate the labyrinth of teenage angst, love, and self-discovery. Noted for its memorable performances and sharp wit, this film is a charming exploration of young love and personal transformation.
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  • The Notebook
    21

    The Notebook

    Ryan Gosling, Rachel McAdams, James Garner
    4 votes
    The Notebook, a romantic drama, sweeps us into the tale of Allie Hamilton (Rachel McAdams) and Noah Calhoun (Ryan Gosling). Set in the backdrop of 1940s South Carolina, it follows the couple's fervent love story from their youthful summer romance to the trials of old age. The narrative unfolds through an elderly man's recollections, Duke (James Garner), reading from his faded notebook to fellow nursing home resident, Miss Hamilton (Gena Rowlands). Directed by Nick Cassavetes and based on Nicholas Sparks's novel, The Notebook won eight Teen Choice Awards in 2005.
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  • Garden State
    22

    Garden State

    Zach Braff, Ian Holm, Ron Leibman
    4 votes
    In Garden State, Andrew Largeman (Zach Braff) returns to his New Jersey hometown after a decade, prompted by his mother's death. A struggling actor in Los Angeles, he's been numbed by prescribed medications, a legacy from his psychiatrist father, Gideon (Ian Holm). Upon returning home, Andrew meets and connects with the eccentric Sam (Natalie Portman), sparking a journey of self-discovery. Directed by Braff himself, this quirky dramedy deftly explores themes of family dysfunction, mental health, and personal growth without resorting to cliches or melodrama. It won the Grammy for Best Compilation Soundtrack Album for a Motion Picture.
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  • Sex and the City
    23

    Sex and the City

    Sarah Jessica Parker, Kim Cattrall, Chris Noth
    8 votes
    Sex and the City is a rom-com drama that sweeps its audience into the bustling, glamorous life of Manhattan. Our protagonist, Carrie Bradshaw (Sarah Jessica Parker), navigates love and friendship with her three best friends - Samantha Jones (Kim Cattrall), Miranda Hobbes (Cynthia Nixon), and Charlotte York (Kristin Davis). Set against a backdrop of high fashion and higher stakes, the movie explores their romantic escapades and personal dilemmas. The film, an extension of the award-winning TV series, cleverly intertwines humor, heartbreak, and hope while showcasing the complexities of modern womanhood.
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  • Sixteen Candles
    24

    Sixteen Candles

    Molly Ringwald, Anthony Michael Hall, Michael Schoeffling
    7 votes
    Sixteen Candles is a classic 1984 coming-of-age comedy directed by John Hughes. The film centers around the character of Samantha Baker, (Molly Ringwald), who's celebrating her 16th birthday but feels ignored by her family who are preoccupied with her sister's wedding. Jake Ryan (Michael Schoeffling), the high school heartthrob, is the object of Samantha's affection while she is relentlessly pursued by a nerdy freshman named Ted, (Anthony Michael Hall). As the day unfolds, hilarious and heartfelt moments ensue, culminating in a memorable birthday that Samantha didn't expect. This film marks an important milestone in teenage films for its honest depiction of adolescent life.
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  • Breakfast at Tiffany's
    25

    Breakfast at Tiffany's

    Audrey Hepburn, George Peppard, Patricia Neal
    8 votes
    In the classic romantic comedy, Breakfast at Tiffany's, Audrey Hepburn stars as Holly Golightly, a young woman with an intriguingly carefree lifestyle in New York City. On the other hand, we see George Peppard as Paul Varjak, a struggling writer fascinated by Holly's elusive charm. The film explores their budding relationship amidst the vibrant backdrop of 1960s Manhattan. Enriched with memorable moments and iconic fashion statements, this movie won two Academy Awards and remains a beloved cinematic masterpiece. Its charm lies not only in its romance but also in its underlying commentary on societal norms and expectations.
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  • Sierra Burgess Is a Loser
    26

    Sierra Burgess Is a Loser

    Shannon Purser, Kristine Froseth, RJ Cyler
    16 votes
    A case of mistaken identity leads to an unexpected romance when a teen joins forces with a popular student to win the heart of her high school crush.
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  • What's Your Number?
    27

    What's Your Number?

    Anna Faris, Chris Evans, Ari Graynor
    7 votes
    Ally Darling (Anna Faris) is realizing she's a little lost in life. Her latest romance has just fizzled out, and she's just been fired from her marketing job. Then she reads an eye-opening magazine article that warns that 96 percent of women who've been with 20 or more lovers are unlikely to find a husband. Determined to turn her life around and prove the article wrong, Ally embarks on a mission to find the perfect mate from among her numerous ex-boyfriends.
  • 13 Going on 30
    28

    13 Going on 30

    Jennifer Garner, Mark Ruffalo, Judy Greer
    8 votes
    13 Going on 30 is a romantic comedy-drama film, a charming tale of childhood fantasies colliding with adult realities. Jenna Rink (Jennifer Garner), an awkward 13-year-old girl, makes a wish to be thirty, flirty, and thriving. To her surprise, she wakes up the next day as a 30-year-old woman living in New York City. Matt Flamhaff (Mark Ruffalo), Jenna's childhood friend, becomes an unexpected yet significant character in her new life. The movie explores Jenna's journey navigating this new world filled with professional success but personal confusion. While grappling with her meteoric rise in a fashion magazine and complex love life, she learns valuable lessons about authenticity and true happiness.
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  • She's All That
    29

    She's All That

    Freddie Prinze, Rachael Leigh Cook, Matthew Lillard
    2 votes
    She's All That is a 1999 romantic comedy, directed by Robert Iscove. The film centers around high school jock Zack Siler (Freddie Prinze Jr.) who, after being dumped by his girlfriend, makes a bet that he can turn any girl into prom queen within six weeks. Enter Laney Boggs (Rachael Leigh Cook), an introverted art student, the subject of Zack's transformation experiment. As Zack navigates the challenges of this undertaking, unexpected feelings begin to emerge. This lighthearted film explores themes of popularity, authenticity, and the unpredictability of love in the high school setting.
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  • When Harry Met Sally...
    30

    When Harry Met Sally...

    Billy Crystal, Meg Ryan, Carrie Fisher
    5 votes
    In the classic rom-com When Harry Met Sally..., Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) find their lives intertwined over a span of 12 years. Initially meeting during a shared car ride from Chicago to New York, their relationship transforms from strangers to friends, challenging the question - can men and women be just friends? Directed by Rob Reiner, this film offers a humorous and touching portrayal of friendship and love. Nora Ephron's witty screenplay, which won a BAFTA award for Best Original Screenplay, brilliantly captures the complexity of modern relationships.
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