(Content warning: This article mentions a movie that takes place at a conversion camp.)
The romantic comedy, or “rom-com,” a term used interchangeably with “chick flick,” and something commonly referred to as “movies I don’t want to watch” by straight men. I disdain how some movies are written off simply because they’re targeted primarily at women, without even knowing what the plot is about. If, however, you enjoy a bit of escapism that includes the highs and lows of romances mixed with the lightheartedness of comedies, and filled with a couple of cheesy stereotypes — you should get into rom-coms.
I personally began to immerse myself in the genre during COVID-19, and now I’m the type of person to have seen the majority of the movies on any typical “Must-Watch Rom-Coms” list. According to “Medium,” there’s six basic components to a rom-com; character introductions, the “meet cute,” the love growing, the turn, the (temporary) break up, and the happily ever after. I like to indulge in both classic takes and clever subversions of this formula. So, in no particular order, here’s a couple of my recommendations to help you test the romantic comedy waters.
10 Things I Hate About You (1999)
This 1999 classic was produced during the “Golden Age” of rom-coms, which extended over the course of the 1990s and is based on the Shakespearean play, The Taming of the Shrew. It stars Heath Ledger (may he rest in peace), Joseph Gordon-Levitt, and rom-com regular, Julia Stiles. Stiles has made other appearances in movies such as Save the Last Dance and The Prince & Me, but I would argue this one is her most memorable.
It is a teen romance and plays into the “opposites attract” and “the bet/lie” stereotypes, but executes them in a way to allow the characters to grow from high school archetypes into three-dimensional people. Bianca Stratford, a local popular girl, isn’t permitted to date until her older sister Kat (Stiles), an unpopular “shrew,” does so. In pursuit of Bianca, Cameron (Levitt) deceives the vain Joey, who is also after Bianca, into paying Patrick (Ledger) to date Kat.
We’ve seen this type of plot before, but the main draw here for me are the “only-in-a-movie” scenes. Some examples include when Patrick serenaded Kat while skipping across the bleachers and the paintball date, both of which are set to a soundtrack of pop rock hits to keep you engaged. The characters defy the expectations tied to their high school roles several times, but the film doesn’t make you question their choices. Instead, it challenges you to question how those roles limit who they’re allowed to be in the first place. The film also provides reasons realistic to high school as to why characters act the way they do. A definite must watch!
To All The Boys I’ve Loved Before (2018)
The one most recent movie on this list is an adaptation of the popular Jenny Han novel. It stars Lana Condor and Noah Centineo, who quickly became a Netflix rom-com darling, but I don’t think there’s a solid argument against this being his best film. Many of the rom-coms produced during the 2000s were overwhelmingly perceived as flops, and the start of the 2010s didn’t have a great reputation either. To All the Boys was an exception though, and has marked what some people say is the beginning of a rom-com renaissance for the 21st-century.
Another teen romance, this time featuring the rom-com tropes of the “fake relationship” and the “love triangle.” 16-year-old Laura Jean Song-Covey (Condor) has kept love letters she wrote to five boys she was previously infatuated with, until one day when the letters are mysteriously mailed. To avoid confrontations with one recipient, Josh, who is not only her childhood friend but her sister’s ex, Laura Jean begins a fake relationship with another recipient, popular boy Peter Kavinsky (Centineo). Peter comes up with the idea in retaliation of his recent ex, Gen.
It’s refreshing to see a female lead express self-assurance without seeking male validation as she does demonstrate comfortability with being on her own. It’s clear to the audience that Peter falls first, and while Lara Jean’s avoidant nature — shaped by her mother’s death — can be frustrating, it’s understandable. Their relationship proves to help push Laura Jean out of her comfort zone from romance novels to developing a healthy romance of her own. Though landing a childhood crush feels like a pipe dream, it’s a good show of the romances people could forge if they moved past high school statuses. I would already go so far as to call it a modern classic.
When Harry Met Sally (1989)
Our first non-teen romance entry, When Harry Met Sally, is one of the films that kick off the “Golden Age” of rom-coms, thanks in large part to rom-com staple Nora Ephron’s script. Yes, it’s the oldest on this list, but holds up so well with the timeless “enemies to friends to lovers” story arc. Not to mention, the performances from leads, Billy Crystal, and another rom-com regular, Meg Ryan, who also starred in You’ve Got Mail and Sleepless in Seattle.
Harry Burns (Crystal) met Sally Albright (Ryan) after they both graduated from college, and Sally’s friend, Harry’s then-girlfriend, suggested they take a road trip together from the University of Chicago to New York City. On this road trip they bicker about the central question that frames the film: can men and women be friends? Harry says no, Sally says yes. They part ways, believing they won’t meet again until five years later when they reconnect at an airport, briefly consider a friendship, but ultimately part again. They will once again reunite five years later in New York City, this time fully attempting to become friends.
What’s interesting about this movie is that Ephron has stated before that her intention was to make this movie more of a character study, driven by internal conflict between the characters. Harry and Sally are held back by their own egos, not external obstacles. Their friends, Marie and Jess, serve as a juxtaposition to Harry and Sally — they’re attracted to one another and they take the opportunity to be together when it comes along. In general, all the characters have their own backgrounds and belief systems, contributing to the world development and authenticity of the film as a whole. It’s an overall crowd pleaser!
Clueless (1995)
Yet another teen romance makes an appearance. Clueless is a modern take on the Jane Austen novel, Emma, where Emma is reimagined as a LA high school socialite rather than an upper society British one. The movie initially seems like it would be a superficial take on its counterpart, but Amy Heckerling’s script and direction added a surprising depth to the characters, comparable to the original.
Alicia Silverstone plays 16-year-old Cher Horowitz, who begins the movie as any other conventional LA-raised queen bee — obsessed with herself and her popularity. Her former step-brother, Josh (Paul Rudd), calls her out on this though, kickstarting Cher’s mission to use her popularity for “good.” This manifests itself in Cher and her best friend Dionne (Stacey Dash) taking on new girl Tai (Brittany Murphy) to transform her into one of their own. I would argue the movie is a coming of age first, but there is the heavy romance subplot and exaggeration of LA stereotypes to give it a comedic effect, so I’m including it on this list.
The movie is an exploration of how the true intentions behind “good deeds” affect their validity. Cher’s actions are driven by self-interest, she befriends Tai and distances her from Trevor to boost her own image, not out of genuine care. Another example of this is when she pairs her teachers together, not for their own happiness, but to get better grades. Once Tai becomes a reflection of Cher in her own right though, Cher realizes the error of her ways. She not only begins to participate in charity work, she reevaluates her perception of people and is able to see them for their value beyond their high school archetypes. Becoming a better person first is framed as a fundamental aspect for building a healthy romantic relationship and serves as a timeless message.
But I’m A Cheerleader (1999)
When you think of LGBTQIA+ forward rom-coms, you most likely think of Love, Simon or Red, White & Royal Blue. I’m going to introduce you to one that’s a bit more niche though, But I’m A Cheerleader. Starring Natasha Lyonne and Clea DuVall, it’s one of the first landmark rom-coms to not only feature a gay lead couple, but also star an openly gay actor, DuVall, who identifies as a lesbian, playing a gay role.
This film is definitely more of the dark humor variety compared to the rest of this list, as it does primarily take place at a conversion camp. It’s a movie we, as a society, never knew we needed. Megan (Lyonne) is a 17-year-old cheerleader who believes she’s straight until her parents and a couple of her friends confront her about being a lesbian. After having this epiphany, her parents send her right to the conversion camp, True Directions, where she meets Graham (DuVall). Here, participants are forced to undergo a five-step program to try and convert them to heterosexuality.
If you’re looking for a film to undertake the horrors of conversion therapy in a realistic and serious manner, then this is not the movie for you. The film exaggerates every element — from set design to script — to underscore the absurdity of conversion camps. The majority of the characters know who they are, but cannot bring themselves to fully accept themselves as they are and endure the camp anyways due to familial blackmail. However, it’s heartwarming to see in the end that the chosen family the characters formed could provide each other with enough support to encourage some of them to stop the conversion process. If you enjoy satirical comedy, then this film could become a guilty pleasure for you.
Hitch (2005)
Since male-led romantic comedies are rare, I thought it would diversify my recommendations if I included one. That isn’t to say that Hitch is anything less than a great film though, especially as one of the few expectations during the general 2000s “rom-com flop” era. It’s quite apparent Will Smith understood his job of creating a charming male lead and Eva Mendes held her own as his counterpart.
Alex (Smith), or as he’s more commonly known as Hitch, is a professional wingman. He gets paid to help men woo the women of their dreams they may otherwise never be able to attract. The main guy who Hitch assists throughout the film’s duration is Albert (Kevin James), who has fallen for one of his clients, Allegra Cole. Hitch also pursues his own love interest, Sara (Mendes), who frequently resists many of his “proven” techniques.
Now, from this description you may misinterpret the objective behind Hitch’s profession — to help men get laid. This idea comes up when a client offers to pay him for that purpose, and Sara confronts him after learning about what type of advisor he is. Hitch not only declines this offer but he also explains to Sara that he is genuinely trying to help his clients find love. It’s uplifting to see a depiction of a man with integrity who reinforces this principle by only assisting those with sincere romantic intentions toward women. I don’t interpret Sara as a so-called “pick me girl” either, she’s focused on her career and is only won over by Hitch once he exceeds her expectations, which is something I think more people should generally aim for in modern dating.
With that, I’ll conclude my list of rom-com recommendations. I don’t say this lightly when I say all of these movies are must-watches, whether you just want to start your journey with the genre or if you’re a casual viewer who could care less about rom-coms. They’re all movies with emotional cores and important messages that go beyond their romantic plots. So get to watching!