Romance films often use on-screen couples to play on tropes that idolize a perfect vision of relationships we should all aspire to. They often include exaggerated gestures of love, compassion, and loyalty that make us root for the couple in question to stay together and live happily ever after, no matter what obstacles they face. However, anyone who’s been in any kind of serious relationship in their adult lives will tell you that real-life love is rarely ever that romantic or simplistic.
Update August 7, 2023: This article has been updated with even more terrible movie couples.
Many people may know the darker and often more realistic side of relationships and just how many different ways a union of two people sharing a romantic interest in each other can soon go awry. Luckily, movies are cognizant of this fact too, and as a result of it, for better or worse, some movies brilliantly depict just how complex, upsetting, or even dangerous relationships can be when they don’t make sense or end up being toxic and unhealthy for one partner, or even both. By paying homage to movies that played the anti-relationship angle well, here’s a look at the worst couples in movie history.
16 Andie and Ben in How to Lose a Guy in 10 Days
After the massive surge of romantic comedies in the 90s, the decade that followed held its own by producing adorable little stories. While some got it right, others tried. How to Lose a Guy in 10 Days follows Andie Anderson, a journalist working under the demands of her overbearing task. When she is tasked with writing an article on how to lose a guy in 10 days, she begins a fake relationship with Ben Barry, who, unbeknownst to her, has also made a bet with his co-workers and is trying to prove that he can make any woman fall for him in a week and a half. Their relationship is problematic from the very start, and the film shows just how manipulation can ruin even the most promising bonds.
Both Andie and Ben are toxic. Their best moments with each other feel awkward and shallow because you know they have dishonest intentions underneath all the smiles and cuddles. Andie constantly pulls mischief and unhealthy ways to tick Ben off, and he continues to put up with it even when he’s raging inside. When they finally start being true to one another, there are serious trust issues. Overall, their fabricated romance does not show even a hint of real chemistry, so when they get together at the end, it’s not exactly fireworks.
15 Claire and John in The Breakfast Club
The Breakfast Club is a quintessential teen drama that broke ground with its premise as well as relatable characters. The movie follows five teenagers from different cliques of high school forced to spend Saturday morning in detention together. By the end of the day, the group turns out to have more in common below the surface than they thought. Claire Standish (Molly Ringwald), the popular girl, ends up with John Bender (Judd Nelson), the criminal.
It’s not surprising that the very differences in their upbringing and way of navigating life are what attract them on a rebellious level. But that’s not enough, is it? Throughout the film, we witness John invading Claire’s personal space by asking her about her sexual experience. He makes fun, pries and ignores her discomfort. Claire only seems to put up with him because he’s “bad.” The one particular scene of John hiding under the desk evokes the most shocking feelings.
14 Oliver and Barbara in The War of the Roses
Talking about love being the death (literally) of two people, The War of the Roses is Danny DeVito’s darling dark comedy about a couple’s ugly divorce. From dividing up assets to showing up for unpleasant proceedings, the movie eventually transforms their separation into an all-out war. Oliver and Barbara seemed like the typical loving pair when they were newlyweds, but over the years, their marriage turned sour. Slowly, they both reveal themselves as two selfish, spiteful, and manipulative individuals who bring out the worst in each other.
At one point, Oliver almost finds himself having a stroke, and Barbara does not even flinch. The scenes that show them fighting over who gets what display just how petty and vengeful their breakup has made them. What started as love morphed into resentment and mistrust, leaving them incapable of even having a tiny conversation without blowing up in each other’s faces.
13 Sandy and Danny in Grease
The musical that still tops the charts when it comes to great performances, energetic songs, and an accurate representation of teenage rebellion, Grease charts around the life of good girl Danny and bad boy Sandy, who meet accidentally while vacationing in Australia. And from there begins a passionate love affair. For a classic set in the 1950s, the movie was quite racy. But that is not the only subject of concern. Danny and Sandy’s transformation as a couple throughout the film brings a lot of toxicity with it.
It starts with Danny talking about Sandy with his friends in a way that hints at more than what actually happened. And later, Danny starts initiating physical intimacy when Sandy is clearly not ready. He tries to change her into a more rebellious version of herself, and to some point, she does. Because we see her in a complete makeover, wearing leather pants and high heels, showing up to school as “queen of the greasers.” The narrative also promotes stereotypical gender roles. Which is why their happy ending leaves a bitter taste in the mouth.
12 Dionne and Murray in Clueless
Directed by Amy Heckerling, this cult classic comedy revolves around the shallow and pretentious teens in Beverly Hills in the 1990s. Cher Horowitz is the popular, rich girl who helps a new student gain popularity and up her social status with a makeover. A trope that has repeatedly been seen in the decade’s teen comedies, it leads to a lot of drama, heartbreak, social navigation, and self-discovery. While all the controversy of Clueless was stolen by the relationship between Alicia Silverstone’s Cher and Paul Dano’s Josh, let’s not forget another couple that was problematic.
Dionne was one of the other popular girls and Cher’s best friend who dates Murray, a good-for-nothing kid from the hood with a lower socioeconomic background. While Dionne is constantly obsessed with her looks, it pains her that Murray is nowhere close to a match. But it’s not like Murray himself is as emotionally mature to understand what it means to be in a serious relationship. Dionne and Murray represent how privilege and ignorance can sabotage a relationship.
11 Jane and John in Mr. and Mrs. Smith
Brad Pitt and Angelina’s 2005 hit film, Mr. and Mrs. Smith, will always be remembered for its behind-the-scenes couples drama since heralded the start of ‘Brangelina.” It also caused the unceremonious end of Pitt’s marriage to ex-wife, Jennifer Aniston. In hindsight, the film was perhaps a little prophetic since Pitt and Jolie began parting ways themselves in 2019. It’s all a little ironic then that in the film that first brought them together, they played a bored husband and wife who later learn that they are both assassins for rival agencies.
They also find out that their latest assignments are to kill each other. In an epic fight scene, the pair physically attack each other, using punches, kicks, and everything else they can to duke it out. As a couple, these two took violence to insane levels, but still manage to find some real passion through it all.
10 Anna and Larry in Closer
As a viewing experience, the 2004 critically acclaimed drama Closer was a brilliant and uncomfortably intense ride. The film centers around two intermingling couples as all partners involved display some stunningly depraved and selfish behavior. Their actions end up pushing everyone involved away from their respective partners and nobody comes out smelling like roses among them.
The film was hailed for its rawness at times as the couples betray each other and have some epic (but brilliantly acted) argument scenes. Although Alice (Natalie Portman) and Daniel (Jude Law) aren’t much better, Anna (Julia Roberts) and Larry (Clive Owen) ultimately get our vote for the more toxic of the two couples. Infidelity is but just a footnote in the laundry list of relational infractions these two meter out against each other in a film that was a startling insight into just how toxic and messy some relationships can be.
9 Brook and Gary in The Break-Up
The film’s title should say it all since The Break-Up, starring Jennifer Aniston and Vince Vaughan, was a film that centered around how a toxic couple end their relationship. The movie, although largely comedic, had some pronounced dramatic and even tragic overtones to it.
Despite starting off as a seemingly happy and committed couple, unspoken resentments ultimately send them hurtling down a path of irreconcilable differences. What follows is a contest of sorts to see who can emotionally hurt the other the most, with a fair degree of pride and immaturity driving all the shenanigans. The way this couple disintegrates ends up being kind of sad since, underneath all the hostility that ensues between them, they both care deeply for each other.
8 Annette and Sebastian in Cruel Intentions
A dark young adult cult classic from the ’90s, Cruel Intentions was a disturbing film in some ways. It displayed the unconscionable actions of rich kids who are so spoiled their narcissistic traits turn them into full-on sociopaths who think rules don’t apply to them. At the center of it are a pair of twisted half-siblings whose penchant for sexual deviancy leads to a wager over whether the brother, Sebastian, can seduce the virginal daughter (Annette) of their private school’s new Headmaster.
Sebastian uses his charms, looks, and a lot of dishonesty to start a relationship with Annette with the intention of seducing her, so they can knock the halo of her famously chastity-preaching head. While the twisted games and plots also make for some compelling subplots too, the main plot revolves around how Sebastian inadvertently ends up falling for Annette. However, his crisis of conscience and newfangled sincere feelings for her are too late to stop the chain reaction that ultimately leads to tragedy. A great film with a killer soundtrack, Cruel Intentions was a lesson in what not to do in a relationship.
7 The Narrator and Marla in Fight Club
To this day, Fight Club, remains a beloved cult classic that’s packed with brilliant and highly quotable dialogue amid a dark and gritty style. While the plot revolves around the two main characters (played by Edward Norton and Brad Pitt, who were both exceptional in the film), an initially nauseating but ultimately weirdly romantic subplot commences between Edward Norton’s character and a woman named Marla Singer (Helena Bonham Carter).
One of them is callous, dishonest, and suicidally depressed, while the other is probably a person suffering from schizophrenia or some form of severe dissociative personality disorder. The result is an unlikely couple that spend frantically passionate and raucous nights together, only for Marla to be viciously kicked out the next morning, her partner claiming to have no idea what she’s doing at his home. If none of this makes sense, you’d probably have to watch the film to know why the compelling plot twist at its end brings everything else into sharper focus.
6 Hermione and Ron in Harry Potter
This one will probably draw the ire of many a Potter fan, but it needs to be said. The three main characters from the globally popular Harry Potter franchise are adored by millions of people around the world. However, as the original books and films develop, many fans couldn’t help but feel that the chief love interest from it never made any sense. On the one hand, there’s Hermione Granger, the brilliant, loyal, sweet, and nerdy girl who proves she can also be the belle of the ball when she wants to.
Rather than make Hermione and the franchise’s main character, Harry Potter himself, fall in love and become an item, the novels’ author, J.K Rowling, chose to match her up with the other best friend, Ron Weasley. In comparison to Hermione, Ron is often impetuous, boorish, slothful, and deliberately nasty at times. For most of the books, Ron and Hermione are virtual opposites but suddenly develop a love interest and even end up married with children at the conclusion of the epic tale. If there were ever seminal words that define the term “incompatible couple,” “Hermione and Ron” would be those words.
4 Bella and Edward in Twilight
Bella and Edward from the Twilight franchise may have a global base of adoring fans, but that doesn’t always stop them from being one of the most toxic and nauseating couples in movie history at times. The pair, who include a vampire and the girl he loves, but longs to kill, also set some atrocious standards for teen and young adult moviegoers, who make up the key demographic of their fans. Chief among these unhealthy traits that define large tracts of Bella and Edward’s relationship is that they reinforce bad choices.
Firstly, they romanticize the notion that it’s okay for young girls to become obsessively in love with men who are dangerous for them, so long as they find the guy devastatingly handsome. When Edward breaks up with her in New Moon, Bella also falls into a deep depression, becomes suicidal, and even deliberately risks her own life just to get a glimpse of Edward. When that doesn’t help, she goes running into the arms of another man who she knows nurses feelings for her, just to drop the second guy like a bad habit the minute Edward is back in the picture.
3 Amy and Nick in Gone Girl
The commercially successful and highly acclaimed psychological thriller, Gone Girl, was a movie that took toxic relationships to egomaniacally extreme levels. The couple from the film is played by Ben Affleck and Rosamund Pike, who both ably portrayed their characters, Amy and Nick’s, darkest traits.
Amy has valid reason to be disgruntled and hurt by Nick since he does step out on her. However, her response was disturbing, to say the least, as she meticulously plots every step of her revenge. That plot involves faking her own kidnapping and apparent murder at Nick’s hands as a way of getting back at him and destroying his life. Revenge is a dish best-served cold doesn’t begin to describe how frosty this couple’s relationship gets by the film’s end.
2 R and J in Romeo + Juliet
In some ways, Romeo and Juliet, in its various cinematic adaptations, is the tale of one of the most famous love stories in history. On the other hand, it probably defines the term “Shakespearian tragedy,” since the film versions are based on what is typically thought to be one of the Bard’s most gut-wrenching plays.
While the pair of star-crossed lovers do experience an intense love story that has gotten many a romance fan’s hearts racing over the centuries, it is also a tale of a couple so bad for each other they literally wind up causing each other’s death. That’s in addition to the fact that their forbidden love reignites an already fractious feud between their families. For sheer bad choices that lead to bad consequences, there’s a reason why these two are known as star-crossed lovers.
Their youthful overzealousness also doesn’t make for a particularly good example for young lovers to follow, no matter how legendary and romantic their love may seem, and it’s on the most cringe display in the 1996 film Romeo + Juliet. The words of Juliet herself pretty much sums up the kind of naive impulsivity that defines them both.
“Or, if thou wilt not, be but sworn by my love, And I’ll no longer be a Capulet”
1 Tessa and Shane in Transformers: Age of Extinction
One typically does not think of romance when they think of Transformers films, but many of the films feature major romantic subplots. While Sam Witwicky and his various girlfriends are extremely unhealthy, the worst is by far the “romance” between Tessa Yeager (Nicola Peltz) and Shane Dyson (Jack Reynor) in Transformers: Age of Extinction. What makes this relationship so awful is the fact that she is a minor, and he is an adult.
The movie offers the terrible justification that they are protected under the “Romeo and Juliet” laws, that since they had a pre-existing relationship when he was 17 and she was 14, it makes it okay for an adult to be in a relationship with a child. Shane even pulls out a laminated piece of paper with the law written on it.
Where to even begin with this? From the predatory nature of pairing an adult and a minor to the fact that the movie stops itself to explain this instead of just making him 17 also is a baffling creative decision. This whole storyline feels gross, and it is no wonder the characters were not brought back for the sequel, Transformers: The Last Knight.