14 Days of Carson’s Specifically Curated Romance Movies and Rom-Coms!

Welcome to 14 Days of RomANDERSON! I’m Carson Schilling, ANDERSON’s resident video editor, motion graphics designer, and unapologetic rom-com enthusiast. Whether you’re riding the post-Valentine’s Day high or need a little cinematic romance to get through the rest of February, I’ve put together 14 specifically curated romance movies and rom-coms, each guaranteed to make you laugh, (ugly) cry, and maybe feel a little too much.

Day #1:
When Harry Met Sally (1989) Directed by Rob Reiner
– Streaming on HBO Max or rental

This is THE best rom-com of all time, and there is genuinely no other correct answer. When Harry Met Sally is a compelling look at two friends and how their relationship evolves over the years. Not only does this movie have some of the absolute funniest moments ever put on film, but it also features Billy Crystal rocking the HARDEST sweater fits of any movie character.

Day #2:
About Time (2013) Directed by Richard Curtis
– Available for rental

Apologies if you’re a diehard fan of The Notebook, but About Time is actually the best Rachel McAdams romance movie of all time. This film is a hilarious and lovely story with amazing performances from its stacked cast, and it has a fun sci-fi element that rocks, too. If you want a movie that will make you uncontrollably sob at the end, this is the one for you.

Day #3:
Palm Springs (2020) Directed by Max Barbakow
– Streaming on Hulu

Another day of a rom-com with a sci-fi twist is upon us because Palm Springs is one of the BEST modern examples of how to make a genuinely original premise out of an ever-popular genre. Andy Samberg and Cristin Milioti are both just insanely wonderful together, and this will make you crack up at every twist and turn, too.

Day #4:
Pride & Prejudice (2005) Directed by Joe Wright
– Available for rental

If you want to truly understand the feeling of longing for someone, Pride & Prejudice is the movie you need to watch. This film is beautifully shot and directed, with some of the best romantic performances of all time. While this film is not entirely faithful to Jane Austen’s original novel, there is no doubt about how impactful and emotional it is. And the hand scene! THE HAND SCENE!

Day #5:
500 Days of Summer (2009) Directed by Marc Webb
– Streaming on Hulu, Disney+, or rental

This absolute gem of indie cinema has become even more iconic over the last 17 years. Whether it’s due to the great chemistry between Joseph Gordon-Levitt and Zooey Deschanel or the memes that have come from the creation of the “manic pixie dream girl” trope, 500 Days of Summer is still a lovely rom-com that will fill your heart with love and laughter no matter what.

Day #6:
La La Land (2016) Directed by Damien Chazelle
– Streaming on Prime or rental

I mean, come on. If you haven’t already seen the pure, romantic movie magic that is La La Land, then you need to get on board. This film is one of my favorite musicals of all time and has some of the most mesmerizing choreography and cinematography of any modern movie. Emma Stone and Ryan Gosling are absolutely amazing together, and the ending is perfect, so FIGHT ME!

Day #7:
Bringing Up Baby (1938) Directed by Howard Hawks
– Available for rental

One of the most underrated horror films of the last few years is Zach Cregger’s Barbarian, because it takes twists and turns you will NEVER guess. This film is such a banger, and if you are a fan of this year’s Weapons, you will absolutely enjoy this completely wild and unpredictable story

Day #8:
Spontaneous (2020) Directed by Brian Duffield
– Streaming on Prime or rental

One of the most underrated and underseen rom-coms I have ever watched is Spontaneous, an amazingly dark and modern take on a high school coming-of-age romance. The performances from Katherine Langford and Charlie Plummer are equally corny and sweet, which is exactly what you want out of a movie like this. Do not watch the trailer; try to go into this movie as blind as possible, because I promise you have never seen anything like it.

Day #9:
The Big Sick (2017) Directed by Michael Showalter
– Streaming on Prime or rental

The Big Sick is another incredibly underrated rom-com that’s as comedic as it is adorable. Kumail Nanjiani and Zoe Kazan are both incredibly hilarious, and the movie also features some of the funniest one-liners ever written. Go in expecting a funny and cute story and leave with one of the most original rom-com stories ever.

Day #10:
10 Things I Hate About You (1999) Directed by Gil Junger
– Streaming on Hulu, Disney+, or rental

One of the best rom-coms and Shakespeare adaptations of all time, 10 Things I Hate About You is a forever iconic movie. Heath Ledger and Julia Stiles are perfectly matched, and this movie has all the best 90s high school nostalgia you could ask for.

Day #11:
Long Shot (2019) Directed by Jonathan Levine
–Available for rental

One of the newer additions to this month’s list is Long Shot, which I think genuinely helped reinvigorate the genre in the 2010s. This movie is INCREDIBLY funny and wonderfully sweet, and you would literally never be able to guess that Charlize Theron and Seth Rogen have so much chemistry together.

Day #12:
Her (2013) directed by Spike Jonze
– Available for rental

This movie gets an unfairly bad reputation because of the subject matter, but I truly believe that Her is one of the best romance movies of the 21st century. Long before AI was taking over literally everything, this film focuses on a genuinely touching relationship between a lonely man and an artificial operating system. I adore how beautiful this movie is, and I hope everyone can understand how ahead of its time it was.

Day #13:
13 Going on 30 (2004) Directed by Gary Winick
– Streaming on Tubi or rental

I actually hadn’t seen this movie until a few years ago (oops). Still, it has become an instant favorite of mine. 13 Going on 30 is a wonderful rom-com that has some of Jennifer Garner’s and Mark Ruffalo’s best performances of ALL TIME, not to mention one of the best dance scenes ever.

Day #14:
Portrait of a Lady on Fire (2019) Directed by Céline Sciamma
– Streaming on HBO Max or rental

The final entry into this year’s list and my personal favorite romance movie of all time is Portrait of a Lady on Fire, which is the definition of unbridled longing. This movie features some of the most beautiful cinematography and set design of any film ever made, and will mesmerize you for its entire runtime. So, if you want a movie that will simultaneously make you believe in true love while also completely shattering your heart into a billion pieces, do I have the perfect period piece for you!