While many classic rom-com movies are still popular and entertaining, the truth is that not all of them have aged well. One of the most popular genres in film is rom-com, offering a good balance between romance, comedy, and drama, with most usually leaning more towards one of these. Every decade has had its dose of rom-coms, but some stand out for having now-classic тιтles.

The 1990s and 2000s were some of the strongest decades for rom-coms, housing some of the most influential movies of this genre. However, and as good and beloved as many of these are, the truth is that many haven’t aged well. This is thanks to specific scenes, themes, or the overall premise of the movie, sometimes even affecting their legacies.

While You Were Sleeping

While You Were Sleeping has all the elements to make a successful rom-com: a relatable main character, a love triangle, and a twist that keeps the audience engaged. While You Were Sleeping was a critical and commercial success, but looking back, it hasn’t aged well thanks to its premise.

While You Were Sleeping follows Lucy (Sandra Bullock), who works at a train station and is secretly infatuated with commuter Peter Callaghan (Peter Gallagher). After Lucy saves him when muggers push him into the tracks, she accompanies a comatose Peter to the hospital, where a nurse and later his family believe she’s his fiancée.

Of course, Lucy plays along, but ends up bonding with Peter’s younger brother, Jack (Bill Pullman). While it could be a “cute” concept on paper, the idea of a complete stranger posing as the partner of a comatose man in front of his family is quite disturbing.

She’s All That

She’s All That is one of the most influential rom-coms of the late 1990s, and despite mixed reviews, it was a box office hit. As fun as She’s All That is, it has aged badly thanks to the rom-com trope it popularized.

She’s All That revolves around the “beautiful all along” trope, with Zack (Freddie Prinze Jr.) betting with his friends that he can turn art student Laney (Rachael Leigh Cook) into a prom queen. Of course, Laney goes through a makeover, which is just Zack’s sister taking Laney’s glᴀsses off and putting light makeup on her.

Zack then sees that Laney has always been beautiful, but doesn’t end the bet nor tells her the truth until his friend mentions it in front of Laney. On top of that, Dean (Paul Walker) faces no consequences for trying to Sєxually ᴀssault Laney, except for temporary deafness.

The Breakfast Club

The Breakfast Club is one of the best movies of all time, and its influence on the genres of rom-coms and teen movies is undeniable. The Breakfast Club broke the stereotypes in teen movies and gave depth to its characters, while exploring themes like idenтιтy, family, and acceptance.

However, the way Bender (Judd Nelson) treats Claire (Molly Ringwald), and one specific scene with them, haven’t aged well. The scene in question is when Bender is hiding under Claire’s desk and decides to put his face between her legs as she’s wearing a skirt. Although Claire does react to it, The Breakfast Club completely brushes it off and has them kissing at the end.

Never Been Kissed

Never Been Kissed performed well at the box office but was a critical failure – however, it has built a cult following thanks to its awkward but relatable character, her self-discovery journey, and its somewhat creative premise of Josie (Drew Barrymore) being an undercover journalist returning to high school.

Josie struggles to navigate high school again, and she falls for her English teacher, Sam (Michael Vartan). Sam reciprocates, but he’s aware that he’s developing feelings for a student. Still, he openly flirts with her, and even though the audience knows she’s not underage, he believes she is. And, of course, the premise of Never Been Kissed is too weird.

Love Actually

Love Actually is one of the most popular and beloved rom-coms of the 2000s, and a must-watch for many during the Christmas season. Love Actually’s success is thanks to its relatable characters, their intertwined stories, and some memorable scenes, such as Hugh Grant dancing around and Andrew Lincoln expressing his feelings for Kiera Knightley.

It’s the latter scene that has made Love Actually age terribly, and since the movie’s release, the perception of it has changed from a romantic gesture to a disrespectful one. Mark (Lincoln) is Peter’s (Chiwetel Ejiofor) best friend, and Peter is married to Juliet (Knightley). Mark acts coldly towards Juliet but only because he’s in love with her.

On Christmas Eve, Mark shows up at Pete and Juliet’s doorbell with a boombox playing Christmas carols and big cue cards, through which he confesses his love to Juliet. This has been pointed out as Mark not respecting Juliet, Pete, and their relationship, even though he moves on after it, with many arguing that he shouldn’t have done it.

Grease

Grease is a classic of rom-coms and musicals, but parts of its story have been heavily criticized for years. Grease is the film adaptation of the 1972 stage musical of the same name, and it was a huge critical and commercial success thanks to its portrayal of the 1950s, catchy songs, iconic dance numbers, and more.

However, there are some scenes and moments from Grease that haven’t aged well at all. Unfortunately, Grease has different references to Sєxual ᴀssault in songs and conversations, and there’s one scene where Danny tries to force himself on Sandy.

Another element of Grease that hasn’t aged well is Sandy’s transformation at the end of the movie. Many have criticized this moment as Sandy completely changes to get back with Danny (after he almost ᴀssaulted her in the car), which has been seen as a terrible example of her search for validation and acceptance.

While it can be argued that Danny did his part in becoming a better person by joining the track team and working on himself behind his friends’ backs, Sandy’s change was way more radical and done literally overnight.

50 First Dates

50 First Dates stands out for the chemistry between Adam Sandler and Drew Barrymore and its unique premise of a woman with a type of amnesia that doesn’t let her make new memories. While many see Henry’s (Sandler) efforts to romance Lucy (Barrymore) every day, the ending of 50 First Dates is now seen as creepy.

In it, Lucy wakes up to yet another tape in which it’s explained to her and the audience that she and Henry are now married, have a daughter, and they are on a boat. The problem with it is that Lucy, with her condition, doesn’t really have any agency.

As a result, Lucy now has to wake up every day with the shocking news of having a family all of a sudden, of whom she doesn’t remember anything.

Sixteen Candles

Sixteen Candles is another John Hughes classic, thanks to its portrayal of relatable characters and the problems and feelings teenagers usually go through. However, Sixteen Candles has been shadowed by controversy due to one character (Gedde Watanabe’s Long Duk Dong), and other elements haven’t aged well.

The main one is Jake’s (Michael Schoeffling) treatment of his girlfriend, Caroline (Haviland Morris), at the party, as Caroline gets too drunk. Jake, tired of Caroline and pursuing Sam (Molly Ringwald), gets the latter’s panties from Ted (Anthony Michael Hall) and, in exchange, gives a drunken Caroline to him, telling him he can do whatever he wants with her because she’s unconscious.

Shallow Hal

Shallow Hal is a classic for the wrong reasons and for how long ago it was released, so it hasn’t exactly been a popular or successful movie (except at the box office). Shallow Hal’s problem is its premise, which initially divided critics and viewers, with some seeing it as a moral lesson and others seeing how problematic it is.

Shallow Hal follows Hal (Jack Black), a Sєxist man who is under a hypnotic guise that makes him see a person’s inner beauty. Thanks to this, he falls in love with Rosemary (Gwyneth Paltrow), a plus-size woman whom he sees as skinny.

While Hal definitely needs to learn a lesson and be a better person, Shallow Hal ultimately perpetuates the toxic message of beauty being linked to a certain size and type of body.

Pretty Woman

Pretty Woman is one of the most successful, popular, and influential rom-coms of all time thanks to its modern Cinderella-type of story and performances, but it hasn’t aged well due to its main themes. Pretty Woman is the story of a Sєx worker, Vivian (Julia Roberts), who is hired by wealthy businessman Edward (Richard Gere).

The two end up bonding and falling in love, but the problem is how Pretty Woman addresses Sєx work, its outdated gender stereotypes, Edward’s behavior towards Vivian and how he exploits her, and its materialistic views. On top of that, there’s a scene where Edward’s friend tries to Sєxually ᴀssault Vivian, which is horrible to watch.