Romance Movies That Get More Inappropriate as the Story Progresses (2024)

Romance movies are a guilty pleasure for many viewers. It's fun to see a fictional romance unfold as a sweet wish fulfillment where a couple overcomes incredible odds to be together. Most of the time, these relationships aren't problematic, and audiences are rooting for the couple to get together. Sometimes, though, romance movies present relationships that are destined for failure through their unsympathetic characters and execution.

Some of these romance films were beloved during their original release but have since fallen out of favor as times have changed and people's appetite for what is deemed acceptable has evolved. Others may have featured relationships that were rotten from the very start and were criticized upon release. Either way, here are the most inappropriate "romances" in romance movies.

Updated February 7, 2024: This list has been updated with even more information about the most inappropriate relationships including even more films and where each title can be streamed.

Silver Linings Playbook (2012)

Patrizio Solitano Jr. & Tiffany Maxwell

Silver Linings Playbook

R

Comedy

Documentary

Drama

Romance

Release Date

September 8, 2012

Director

David O. Russell

Cast

Jennifer Lawrence , Robert De Niro , Bradley Cooper , Julia Stiles , Chris Tucker , Shea Whigham

When talking about polarizing romance movies, chances are many will find Silver Linings Playbook popping into the discussion. A critical and commercial darling during its time of release, Silver Linings Playbook sees Bradley Cooper starring alongside Jennifer Lawrence as Patrizio Solitano Jr. and Tiffany Maxwell, respectively. Both have some deep personal issues to resolve, with Tiffany dealing with the loss of her partner and Patrizio attempting to reconnect with his wife, Nikki (Brea Bee), after an extended stay at a psychiatric hospital. When Patrizio and Tiffany pair up in a mutual friendship, they may find themselves forming a connection neither of them thought was possible.

Pat & Tiffany's Toxic Tango

For starters, Pat and Tiffany are nowhere near ready for a relationship at any point during Silver Linings Playbook. The inherent problem with their relationship is that for the majority of the movie, Pat mistreats Tiffany, constantly belittling her and, ultimately, using her to get a message across to Nikki. Then there's Tiffany, who compulsively lies to get closer to Pat. This relationship feels like a train wreck waiting to happen through and through, and though the film ends on a high note, viewers can't help but wonder what will happen after the credits roll.

Stream on Netflix

The Graduate (1967)

Benjamin Braddock & Mrs. Robinson

The Graduate

PG

Comedy

Documentary

Drama

Romance

Release Date

December 21, 1967

Director

Mike Nichols

Cast

Anne Bancroft , Dustin Hoffman , Katharine Ross , William Daniels , Murray Hamilton , Elizabeth Wilson

Widely regarded as one of the greatest films of all time and a major cultural touchstone, The Graduate famously stars Dustin Hoffman as fresh college grad Benjamin Braddock, who finds himself pondering what direction he should take in life while engaging in a torrid, secret affair with the restless housewife Mrs. Robinson (Anne Bancroft). Things quickly become even more complicated for the struggling 21-year-old when he begins to fall in love with the older woman's daughter Elaine (Katharine Ross), much to Mrs. Robinson's disdain.

A Majorly Problematic Classic

Not only is their relationship deplorable because Mrs. Robinson is married to one of Benjamin's father's business partners, but the whole nature of their romantic dalliance is extremely inappropriate and alarming. Aside from the large age disparity and the fact that they're having an affair, Mrs. Robinson manipulates Benjamin and uses his naivety for her benefit, and has no problem stripping him down in an attempt to lure him into the bedroom. The question of consent swiftly rears its head in the film, and while Benjamin is no prize himself, the nature of their fling and its unsettling undertones makes rewatching The Graduate difficult for modern audiences.

Rent on Prime Video

Fifty Shades of Grey (2015)

Anastasia Steele & Christian Grey

Fifty Shades of Grey

R

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Drama

Documentary

Romance

Thriller

Based on the book by E.L. James, Fifty Shades of Grey is the first film in the trilogy that follows naive literature student Anastasia Steele (Dakota Johnson), whose life changes upon meeting the complicated and tormented billionaire Christian Grey (Jamie Dorman). Drawn to each other, the two start a romantic relationship where Steele uncovers Grey's secrets - and explores her own personal desires.

Release Date

February 11, 2015

Director

Sam Taylor-Johnson

Cast

Dakota Johnson , Jamie Dornan , Luke Grimes , Jennifer Ehle , Eloise Mumford , Rita Ora

For many, Fifty Shades of Grey needs no introduction. Originally written as a piece of Twilight fan fiction, it has since been reworked into a successful romance series spanning several books and feature-length films. Of course, the focus is about the latter today, which saw Dakota Johnson starring alongside Jamie Dornan as Anastasia Steele and Christian Grey, respectively. The film sees Steele, a literature major, securing an interview with Grey, a billionaire, following a sudden vacancy in her schedule. Soon after, Steele and Grey quickly enter a relationship that pushes more than just a handful of boundaries.

Startling Control Issues

Fifty Shades of Grey is hard to sit through, all due to Christian's control issues throughout his relationship with Anastasia. While Christian claims he wants to help Anastasia explore her sexuality, the truth of the matter is, Christian is a self-serving individual that will say anything to get Anastasia to go along with his desires. Matters worsen in Fifty Shades Darker and Fifty Shades Freed, as Christian's past relationships, enemies, and traumas take a toll on the relationship, and put Anastasia's life in danger. Christian had significant healing to do before attempting a relationship with anyone.

Stream on Max

Sixteen Candles (1984)

Sam Baker & Jake Ryan

Sixteen Candles

PG

Comedy

Romance

Release Date

May 4, 1984

Director

John Hughes

Cast

Molly Ringwald , Justin Henry , Michael Schoeffling , Haviland Morris , Gedde Watanabe , Anthony Michael Hall

John Hughes dominated the 1980s with movies like Sixteen Candles, his feature-length directorial debut. A coming-of-age film, Sixteen Candles is the film that would famously shoot Molly Ringwald to stardom, with ample praise given to Michael Schoeffling and Anthony Michael Hall as well. Ringwald plays Samantha Baker, a teenager who recently turned 16. However, after her parents forget such a momentous occasion, Sam is left to her own devices in order to grab the attention of her crush, Jake (Michael Schoeffling). Meanwhile, a first-year student, Ted (Anthony Michael Hall), tries to act on his feelings for Sam.

Misogyny Runs Rampant

Yikes, John Hughes really missed the mark with Sixteen Candles. How this used to be considered a wholesome, coming-of-age rom-com is unfathomable. Sixteen Candles perpetuates misogyny and unhealthy attachments. Ted doesn't respect Sam's boundaries and, at one point, sexually assaults her. Sam ends up with Jake, but he is only the healthier option over Ted because he doesn't commit physical acts of violence towards Sam. What makes matters worse is that Sam is objectified throughout the entire film.

Stream on Netflix

No Hard Feelings (2023)

Maddie Barker & Percy Becker

No Hard Feelings

Comedy

Release Date

June 23, 2023

Director

Gene Stupnitsky

Cast

Jennifer Lawrence , Ebon Moss-Bachrach , Natalie Morales , Matthew Broderick , Laura Benanti , Jordan Mendoza

No Hard Feelings is a controversial romantic comedy that feels like it was ripped straight out of the 2000s. Jennifer Lawrence plays Maddie Barker, a woman who is down on her luck and facing some pretty dire financial straits. When she stumbles across a bizarre job posting that asks for someone to "date" their son, Percy (Andrew Barth Feldman), Maddie is more than enthusiastic to put herself forward. However, the nature of their relationship eventually starts to dissolve Maddie's professional boundaries, leaving the two in a bind when Percy is set to attend college in the fall.

Flipping the Rom-Com Script

This isn't the worst relationship on this list, but Maddie and Percy's entire dynamic is cemented by one big lie. The whole point of the movie is to subvert the usual formula where a guy pursues a girl and so on, and No Hard Feelings achieves this well. But this is at the cost of Maddie's overall likability. Perhaps the most unnerving part of this relationship is seeing Maddie uphold her lie up until the very last moment of intimacy between her and Percy, where he finally confesses to knowing about Maddie's deal with his parents. It's difficult to imagine that Percy would ever trust Maddie again, or even contemplate a friendship.

Stream on Netflix

Trainwreck (2015)

Amy Townsend & Aaron Conners

Trainwreck

R

Comedy

Romance

Release Date

July 17, 2015

Director

Judd Apatow

Cast

Colin Quinn , Devin Fabry , Carla Oudin , amy schumer , Josh Segarra , Ryan Farrell

Trainwreck, if it wasn't already obvious, is a Judd Apatow flick through and through. Stand-up comedian Amy Schumer both wrote and starred in this rom-com as Amy Townsend, an energetic woman who struggles with commitment. However, as she starts to grow more and more attached to Aaron Conners (Bill Hader), she may find her old way of life uprooted with all the struggles that come with it.

A Downright Unlikable Lead

The biggest issue with Trainwreck is that its lead, Amy, is pretty reprehensible. Amy is selfish and irresponsible, and dismisses just about anyone that isn't serving her immediate needs. Seeing Amy and Aaron get together feels contrived; Aaron spends his life helping others, and Amy spends her life helping herself. The most glaring problem with this relationship is Amy's emotional unavailability; she is hesitant to commit to Aaron, takes him for granted, and reacts cruelly to his love confession. Though the film ultimately ends with the two getting together, it was certainly a rough journey getting there.

Stream on Max

Love Actually (2003)

Juliet & Mark

Love Actually

R

Comedy

Documentary

Drama

Romance

Release Date

September 7, 2003

Director

Richard Curtis

Cast

Bill Nighy , Gregor Fisher , Rory MacGregor , Colin Firth , Sienna Guillory , Liam Neeson

Love Actually is one of the most famed rom-coms on this list, and for good reason. Richard Curtis directed this Christmas-themed rom-com in 2003, telling the stories of ten separate characters whose paths occasionally cross throughout. An ensemble cast comprised of names like Hugh Grant, Liam Neeson, Colin Firth, Laura Linney, and Emma Thompson, made this film a huge success both critically and commercially, developing a cult following that persists to this day. There are some really touching relationships depicted in Love Actually. But then there's Juliet (Keira Knightley), Peter (Chiwetel Ejiofor), and Mark (Andrew Lincoln).

Three's a Crowd?

Juliet is married to Peter, but her loyalties are torn between her commitment and Mark's love confession. To make matters worse, Juliet is unfaithful to Peter by kissing Mark on Christmas Eve, as Peter is only feet away inside their home! Though this relationship led to one of Love Actually's most famous scenes, Juliet's marriage seems ultimately destined for failure.

Buy or Rent on Prime Video

The Blue Lagoon (1980)

Emmeline Lestrange & Richard Lestrange

Chronicling the harrowing ordeal two young children experience after becoming marooned on a South Pacific tropical island, Randal Kleiser's The Blue Lagoon starred Brooke Shields and Christopher Atkins as Emmeline and Richard Lestrange, cousins who managed to survive a deadly shipwreck and must learn to survive and fend for themselves on the secluded island. Together, the pair grow up outside of the watchful eye and influence of traditional society and begin a complicated and unsettling romantic relationship.

An Unsettling Taboo Relationship

The Blue Lagoon is not an easy film to watch, as the incestuous romance between the two cousins is hard to look past and it makes their overall innocence and sexual discovery feel disquieting. The fact that Shields was just 14 years old when she appeared in the film, while Atkins was 18, only makes their "romance" that much harder to stomach. The actors were scantily clad in many scenes and despite the young characters not knowing any better in the coming-of-age picture, their relationship was extremely inappropriate and highly taboo by today's standards.

Stream on Max

The Holiday (2006)

Iris Simpkins & Jasper Bloom

The Holiday

PG-13

Comedy

Romance

Release Date

December 8, 2006

Director

Nancy Meyers

Cast

Cameron Diaz , Kate Winslet , Jude Law , Jack Black , Eli Wallach , Edward Burns

Another Christmastime rom-com, The Holiday places Kate Winslet and Cameron Diaz into the roles of Iris Simpkins and Amanda Woods, respectively. Though Iris' feelings for her ex-boyfriend, Jasper (Rufus Sewell), still linger in her heart, she'll have to find a way to move on when Jasper does the same. Meanwhile, Amanda goes through a tense breakup with her boyfriend, Ethan (Edward Burns), prompting her to find somewhere else to live for a time. The two women find themselves crossing paths as they trade places, with Amanda leaving the United States for London and vice versa. Will they find love internationally, or will they wind up reopening old wounds?

Devastating Unrequited Love

The inappropriate relationship here has to be the one shared between Iris and Jasper. Iris is simply too good for Jasper, so it's difficult to imagine that they were in a relationship at some point in history. Jasper doesn't only cheat on Iris, he uses Iris to delegate much of his work, knowing she'll comply due to her unrequited love for him. Jasper's relentlessness is uncanny as he travels all the way to California to pressure Iris into helping him with work; fortunately for Iris, she puts a definite end to a highly manipulative relationship.

Stream on Netflix

Twilight (2008)

Bella Swan & Jacob Black

Twilight

PG-13

Drama

Adventure

Documentary

Fantasy

Romance

Release Date

November 20, 2008

Director

Catherine Hardwicke

Cast

Kristen Stewart , Robert Pattinson , Billy Burke , Peter Facinelli , Elizabeth Reaser , Cam Gigandet

It was only a matter of time before Twilight was mentioned. One of the most popular romance franchises for a time, Twilight puts a new spin on vampires as the ailing Bella Swan (Kristen Stewart) is brought face-to-face with Edward Cullen (Robert Pattinson). The two quickly hit things off at their local high school. But, as Edward's supernatural abilities place Bella in danger, their relationship may inadvertently lead to their mutual demise.

A Tumultuous Love Triangle

Some would argue that the inherent problem with this relationship is rooted in Bella and Edward being teenagers — even though Edward is mentally over one hundred years old. Nevertheless, Bella's relationship with Edward isn't the most inappropriate dynamic in the Twilight series; it's Jacob Black's obsession with Bella. Jacob is the third piece of Twilight's love triangle, and though plenty of adoring fans rooted for Team Jacob during the franchise's heyday, it's hard to see why in retrospect. Jacob stalks Bella, lashes out at her when things don't go his way, and at one point, forcibly kisses her. Jacob needed to stay far, far away from Bella instead of becoming her son-in-law!

Buy or Rent on Prime Video

A Star Is Born (2018)

Jack Maine & Ally Maine

A Star is Born

R

Musical

Documentary

Drama

Romance

Release Date

October 3, 2018

Director

Bradley Cooper

Cast

Bradley Cooper , Lady Gaga , Andrew Dice Clay , Sam Elliott , Dave Chappelle

A Star Is Born, based on the poster, looks like a typical uplifting romance story. The actual film, however, is emotionally devastating. Bradley Cooper stars as Jack Maine, an aging country rock singer whose struggles with drug addiction continue to take a firm hold on his life. After a routine trip to a bar, however, Jack discovers Ally (Lady Gaga), an up-and-coming musician who Jack immediately falls for. Unfortunately, after giving Edith the promise of a big break, their relationship is fraught with the biggest challenges either person has ever faced.

Tragic Turn of Events

Initially, Jackson shows a humble side to him that gives Ally her big break when no one else will. While their relationship is seemingly healthy in its early stages, things quickly take a turn for the worse as Ally's career flourishes while Jackson's declines, all due to his substance abuse. Ally remains by Jackson's side until the bitter end, and it takes an enormous emotional toll on her. As toxic as it is, their incredibly sad relationship may hit close to home for those who experienced drug abuse firsthand.

Buy or Rent on Prime Video

Big (1988)

Josh Baskin & Susan Lawrence

Big

PG

Comedy

Drama

Fantasy

Release Date

June 3, 1988

Director

Penny Marshall

Cast

Tom Hanks , Elizabeth Perkins , Robert Loggia , John Heard , Jared Rushton , David Moscow , Jon Lovitz , Mercedes Ruehl

While there is no denying that Penny Marshall's romantic dramedy Big is a universally lauded '80s hit, having helped catapult Tom Hanks to superstardom, that doesn't mean the plot of the fantasy flick didn't get a little...questionable at times. It centers on twelve-year-old Josh Baskin as he is magically transformed into a 30-year-old after making a wish with a fortune-teller machine. The boy awakens as a full-grown man and sets out to New York City in hopes of finding a way to undo his wish and return to his old life.

Cringe-Worthy Romantic Implications

After taking a job at a toy company while he bides his time, Josh catches the eye of fellow employee and executive Susan Lawrence (Elizabeth Perkins) and a romantic relationship blossoms between the two. Though Marshall did an admirable job towing the line of Josh's childlike innocence with the more adult undertones, the fact that Susan takes him to her apartment and it is implied that they have sex after she removes her shirt is definitely creepy. He has a 12-year-old's psyche, and even Perkins acknowledged in a 2021 interview how the scene and implication wouldn't fly in Hollywood today:

"If you look at it in the movie, it was sort of used as a joke. Here he is the next morning, the elevator door opens and he bounces out like: ‘Wow, I just had my first sexual experience.' It was a setup for a joke that today would not be acceptable.”

Stream on Disney+

Never Been Kissed (1999)

Josie Geller & Sam Coulson

Never Been Kissed (1999)

PG-13

Comedy

Romance

Release Date

April 9, 1999

Director

Raja Gosnell

Cast

Drew Barrymore , David Arquette , Michael Vartan , Leelee Sobieski , Jeremy Jordan , Molly Shannon , Garry Marshall , John C. Reilly

Raja Gosnell directed Never Been Kissed in 1999, rounding out the list of the most inappropriate romances in movies. The film features Drew Barrymore as Josie Geller, a copy editor for a prestigious newspaper whose relationship follies continue to plague her love life. When Geller is given a special investigative assignment at a local high school, her life takes a turn for the worse as painful memories flood back in about how she was treated during her adolescence. Things turn around when she finally meets Sam Coulson (Michael Vartan), her English teacher, as she quickly finds herself attracted to him. But as the two commit to their respective jobs, what will ultimately happen when the truth comes out?

A Relationship Built on Lies

Arguably the most inappropriate couple on the list, Never Been Kissed convinces audiences into rooting for Josie and Sam to get together by the end of the film when, in reality, they both deserved to be out of a job. This relationship is cemented by lies, manipulation, and predatory behavior. Sam is in a position of power as Josie's teacher, and while she is an adult, he doesn't know this, believing she is another one of his teenage students. Sam only has a problem with their relationship when he discovers Josie is actually age-appropriate! Sure, Josie lied for personal gain, but Sam was a reprehensible person that had no business working in a school setting.

Buy or Rent on Prime Video

Overboard (1987)

Dean Proffitt & Joanna Mintz-Stayton

Beginning a relationship based on lies and manipulation doesn't exactly bode well for the longevity of said romance, and Garry Marshall's classic romantic comedyOverboard only proves this assertion. Hollywood power couple Goldie Hawn and Kurt Russell famously shared the screen in the '80s staple, which focuses on the snobby heiress Joanna Stayton as she suffers from amnesia after falling from her luxurious yacht. Carpenter Dean Proffitt was treated poorly by Joanna and he decides to make the most out of her unfortunate predicament and pretends that she is actually his wife.

Lies & Deceit Run Rampant

Dean sets out to exact revenge against the spoiled Joanna and not only lies about being her partner but also makes her work off the bill she never paid him for. He spends a good portion of the flick gaslighting Joanna and making her question her instincts and herself, and though she may have had it coming to a degree, it's hard to root for the mismatched duo and their romance when it's built on a pile of lies and deceit.

Buy/Rent on Apple TV+

Tired of inappropriate relationships? Looking for something a bit more wholesome? Why not check out our video about the most heartwarming friends-to-lovers movies?