CultureHead Magazine

I know that a lot of children are traumatized by movies like The Shining or A Clockwork Orange, but I personally never really got over View From the Top, an obscure romantic comedy where Gwyneth Paltrow gives up her dream job of being an international flight attendant to live in Cleveland with her boyfriend, Mark Ruffalo. My aunt lent it to my mom on a VHS tape. Even as a 10-year-old, I could not wrap my head around why someone who just spent an entire movie working hard and chasing her dream dropped everything because her boyfriend does not want to move out of Ohio? 

It is a pattern in romantic comedies. In the iconic You’ve Got Mail, Tom Hanks literally puts Meg Ryan out of business, and she ends up with him anyway. Even in 13 Going On 30, we are never shown whether Jennifer Garner’s character grew up to become the successful magazine editor she apparently wanted to be. We only know that she has happily settled with Mark Ruffalo, who was apparently the bane of my adolescence, in the suburbs. 

The abundance of coded messages young girls and women receive about men being the most valuable resource worth sacrificing everything for is truly baffling. But as someone who still thoroughly enjoys (and not even in an ironic cool way) the genre of romantic comedies, it always saddened me that I had to turn off my skepticism and frustration when tuning in to watch the majority of popular rom coms. It does not have to be this way though. 

So, in order to avoid traumatizing the new generations, or to heal your inner child, here’s a list of ten romantic comedies that break away from this trope and that give you your desired dose of healthy escapism without asking you to completely suspend your disbelief that anyone would choose Ross over a job in Paris (yes, it’s from a TV show but can you think of a better illustration of what I’m talking about than Ross & Rachel from Friends?). 

1. Always Be My Maybe

10 Rom-Coms Where the Heroine Doesn't Settle CultureHead Magazine
Randall Park and Ali Wong in Always Be My Maybe. Courtesy of Netflix

This movie takes the girl next door and childhood friends tropes and treats them with so much humor and respect. Ali Wong and Randall Park, who both cowrote the movie along with Michael Golamco, manage to make their characters equally complex and into each other. Always Be My Maybe avoids making its audience feel like Wong’s successful character would be settling for her childhood crush by making Randall’s character go through a believable development arc. 

2. The Incredible Jessica James

10 Rom-Coms Where the Heroine Doesn't Settle CultureHead Magazine
Jessica Williams in The Incredible Jessica James. Courtesy of Netflix

This movie is a hidden gem and a great post-breakup watch! If you happen to be in your mid or late twenties and feeling utterly uninspired (just speaking from experience here), maybe you could relate to Jessica Williams’ character in this one. She is well-written and seems too badass to ever drop everything for a man. 

3. To All the Boys: Always and Forever

10 Rom-Coms Where the Heroine Doesn't Settle CultureHead Magazine
Lana Condor and Noah Centineo in To All the Boys: Always and Forever. Courtesy of Netflix 

This is a three-in-one kind of deal. Although, I am particularly a fan of how things resolved in the final part of this Netflix trilogy. I wish this movie was around when I was a teen and not only because I’d love to watch an Asian lead on-screen. To All the Boys: Always and Forever does a good job of merging hopeless romanticism with facing the real world, which makes the movie a perfect ending for Lara Jean and Peter. 

4. Sleeping with Other People

10 Rom-Coms Where the Heroine Doesn't Settle CultureHead Magazine
Alison Brie and Jason Sudeikis in Sleeping with Other People. Courtesy of IFC Films

Dysfunctional adults learning to distinguish love from the ego-driven obsession? Sign me up. Alison Brie and Jason Sudeikis have great chemistry. You kind of trust them to not screw this one up. They also get high and attend a child’s birthday. 

5. Set It Up

10 Rom-Coms Where the Heroine Doesn't Settle CultureHead Magazine
Zoey Deutch and Glen Powell in Set It Up. Courtesy of Netflix 

Honestly, the movie would have worked for me even if the main characters did not get romantically involved. 

It’s about dating as an overworked and underpaid millennial. Both characters appear equally far from their dream jobs and are bad at figuring out what they want. Of course, that is until they meet each other! Also, Zoey Deutch’s character’s sentimental obsession with sports is the representation I never thought I needed. 

6. Someone Great

10 Rom-Coms Where the Heroine Doesn't Settle CultureHead Magazine
Gina Rodriguez and Lakeith Stanfield in Someone Great. Courtesy of Netflix 

Another breakup movie. The plot revolves around Gina Rodriguez’s character getting a dream job (in a magazine, of course. Rolling Stone to be precise.), which promptly leads to the end of her nine-year relationship. Thankfully, she never questions whether she should take the job and whether leaving her comfort zone is the right thing to do. It’s a good start and already way more than the majority of breakup movies have given us before. 

7. Bend It Like Beckham

10 Rom-Coms Where the Heroine Doesn't Settle CultureHead Magazine
Parminder Nagra and Jonathan Rhys Meyers in Bend It Like Beckham. Courtesy of Fox Searchlight Pictures

First of all, the fact that this movie is not about Parminder Nagra and Keira Knightley’s characters falling in love is a crime (I prefer to think of the movie’s ending as a beginning of their relationship and no one can change my mind). I guess, Jonathan Rhys Meyes is there. I guess, he is the main romantic interest. Anyway, a 2002 hit romantic comedy written and directed by a brown woman and starring a brown woman whose character grapples with her cultural background and her unconventional professional dreams? And she succeeds? And she doesn’t stop for any guy? Talented, brilliant, incredible, amazing, never the same, totally unique, completely not ever been done before.

8. Legally Blonde

10 Rom-Coms Where the Heroine Doesn't Settle CultureHead Magazine
Alanna Ubach, Reese Witherspon, and Jessica Cauffiel in Legally Blonde. Courtesy of Everett Collection 

Also known as the backbone of Girl Power Feminism. This film should be studied as a primary source of the way we study The Feminine Mystique. 

Okay, this is also a tricky one. Technically, iconic Elle Woods does drop everything to be with a man in this film. But we all know how this turns out for her. This movie was so satisfying for me to watch as a child and that’s all I will say. 

9. Obvious Child

10 Rom-Coms Where the Heroine Doesn't Settle CultureHead Magazine
Jenny Slate in Obvious Child. Courtesy of A24

Another trope in the media that I hate? Apparently, every woman wants to be a mother. Even the ones who tell you they don’t. I cannot count all the times I have had to watch a woman get accidentally pregnant and decide to keep the baby despite not being ready or saying she does not want to have children earlier in the movie. Four Christmases and Love Life on HBO come to mind out of the recent ones I saw. 

So, when a friend of mine recommended Obvious Child as a film that realistically depicts the choice of millions of women regarding accidental pregnancies, I was pleasantly surprised to say the least.

10. 10 Things I Hate About You

10 Rom-Coms Where the Heroine Doesn't Settle CultureHead Magazine
Heath Ledger and Julia Stiles in 10 Things I Hate About You. Courtesy of Buena Vista Pictures

Finally, another teenage classic. Now, technically in the movie Julia Stiles’ character does not face a dilemma of choosing between her career/education and love. She does, however, get back together with her bad-boy boyfriend just after prom and we also know that she was very excited about being admitted to Sarah Lawrence, a college located far away from her home in Seattle. Call me naive, but I trust Kat to make a reasonable choice and pursue the education she wants. 

Bonus: La La Land

10 Rom-Coms Where the Heroine Doesn't Settle CultureHead Magazine
Ryan Gosling and Emma Stone in La La Land. Courtesy of Lionsgate

I do not consider La La Land a romantic comedy nor would I want to rewatch it any time soon. It is just too long. However, if you are looking for a realistic depiction of choosing between growing together and growing apart, this movie might be for you.

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