Our Favorite Fall Rom-Coms
We do the season justice with 'When Harry Met Sally,' 'You've Got Mail,' 'Scott Pilgrim,' and more.
It’s October, baby. The leaves are turning red, the ghosts are coming out, Billie Holiday is singing “Autumn in New York” and we’re desperately clinging to her every word. Fall is a time for love, for relationships! As is with every season, when you’re watching a rom-com. The best thing about Fall is the turtlenecks. The second best, of course, is when rom-com characters jazz them up in a spiffy little outfit.
Some of these films take place over multiple seasons — to that we say, who cares? Autumn is there, at least in glances. Here we rank our favorite fall rom-coms, which though only a handful, are among the cream of the crop.
When Harry Met Sally… (1989)
Annabelle: This was a no brainer for me. If you don’t already know that When Harry Met Sally… is my favorite rom-com, I don’t know what to tell you. Are you paying attention at all? I’ve mentioned it so many times. Obviously, it’s at the top of this list. Who do you think I am? More on this to come.
Fletcher: As I stressed earlier: the turtleneck game is unmatched. Yes, When Harry Met Sally takes place over several seasons — and yes, we will probably feature it in our winter round-up, unapologetically so! Although the Central Park and Met scenes are probably the biggest Fall fad, the voiceover phone bit is understated. These conversations are soothingly autumnal: there’s no more summer, no more hanging out with people in parks, beaches, outside. Lots of phone calls. Lots of texts. Lots of introspection.
Silver Linings Playbook (2012)
that fit… it has been added to my vision board
Fletcher: “I’m making crabby snacks and homemades!” shouts Jackie Weaver, at her sweater-don son Bradley Cooper and cranky husband Robert De Niro. This film is a hoot. I giggle everytime I see Coop in a groutfit; but I’m also a bit envious of his Fall running get-up. While I don’t really miss Fall in the suburbs at home, I do enjoy the warm feeling of nostalgia when I watch this. And those iPods!
You’ve Got Mail (1998)
her black turtleneck. a woman after my own heart
Fletcher: Traditionally thought to be a Spring movie, You’ve Got Mail is, in my opinion, more Fall-y. Yes, these two do fall in love in the Spring, and there’s the whole daisy bit. The Autumn sequence to “Dreams” by The Cranberries always grabs me: Meg Ryan bustling in her turtleneck and little boots, Tom Hanks pushing through leaves to grab a toasty cup of coffee. Bookstores are better in the Fall, too. And there’s that leaf-ridden scene at the kiddie fair, too, where Hanks presses his face into a turkey cut-out.
Scott Pilgrim vs. The World (2010)
the way he’s gripping the cup… every teen has felt like this
Annabelle: The first time I watched Scott Pilgrim vs. The World I was in my friend’s college dorm, unaware of what was about to hit me. The second, third, and fourth times I watched Scott Pilgrim were in my bed, at 3 a.m., when I needed it most. Some may say that this movie is not a rom-com, to that I say, you’re right! It’s a masterpiece. Bothers me a little bit that a lot of people don’t understand the point of this movie is “nice guys” aren’t always nice but, whatever. They wrote in the lines “I’m a little bi-furious!” so don’t even try to argue with me.
The Corpse Bride (2005)
Fletcher: I haven’t seen this in ages, to be fair. There need to be more Halloween rom-coms. Do you remember what Victor’s actual bride looks like? Probably not, because she’s so forgettable. Look at that Corpse Bride — she’s gorgeous! My point is that the love triangle here is fun, you root for the Corpse Bride.
Juno (2007)
Annabelle: Though this technically spans more than just fall since Juno has to carry her baby to full term, it qualifies because the majority of the climactic scenes happen in the fall when Juno and Michael Cera (what’s his character’s name again? It doesn’t even matter honestly) have sex and slowly fall in love. Not going to apologize for the amount of Michael Cera on this list! He and Meg Ryan are fall rom-com deities.
Rushmore (1998)
Fletcher: Look at Rosemary and Max in their sweet little Fall layers. School flicks are a trend with this list, due to the fact that back-to-school themes are very autumnal. Though Rushmore is one of the more eccentric films on our list, it’s coming-of-age, it’s romantic, and it’s full of blazers and sweaters. Plus, Queen of all things Autumn Rory Gilmore (Alexis Bledel) has a role as an extra.
The Lobster (2015)
coincidentally every boy that recommends me the lobster also looks like this
Fletcher: Adding more ponchos to my regimen, thanks to The Lobster. This is not a rom-com, if we’re looking deeper, but it is both romantic and quite comedic. Some folks may argue that it is not even humorous — but it is, truly, in my opinion. I love hearing their feet crunch as they tip-toe through the forest. And I love their little symbols to one another. I’ve played games like this.
Annabelle: This movie lives rent-free in my brain because I am convinced that if this were a Black Mirror episode it would have done insane numbers. Instead, white boys that read books and have a god complex love to tell me that this is their favorite movie on dates. It’s pretty good though and the poster is the reason why my friend Andrew got into graphic design, so, it’s at least good for something! Hi Andrew!
Legally Blonde (2001)
Annabelle: Being from Boston (embarrassing!), I can fully say that this is the best Boston movie besides The Kissing Booth 2. Elle Woods is an icon like no other, lawyer extraordinaire. If I suddenly give it all up and decide to be a lawyer, know for sure Elle Woods is the reason. I love story plots that involve getting back at an ex-boyfriend-- love to be a part of one someday.
Love, Simon (2018)
Fletcher: They get iced coffee when it’s cold, guys. Seriously. Watching Simon drive a car full of friends feels like I’m in high school again, and it’s Homecoming Week. Will someone ask me? No. But I will drive my friends to all the events, after we’ve tie-dyed shirts and braided each other’s hair — all while gossiping about crushes, obviously.
Annabelle: Shawn Mendes didn’t sing “Wonder” for us not to put Love, Simon on our favorite fall rom-coms list. Remember when he went to go see this in the theatres and cried because he was worried people would think he was gay? Remember when he auditioned for the role of Simon? What could’ve been.
Honorable Mentions:
After (2019)
Annabelle: Not technically a romcom, because all the com is unintentional, but would not be able to claim our #bookishvibes without including it on this list. BTW, Hardin’s friend who is the “Zayn” character in the story is played by Joe from Glee- remember that Jesus guy with the dreads? Just had to share.
The Kissing Booth (2018)
Annabelle: Of course, if it actually took place in Fall The Kissing Booth would be top of this list. It’s our NAMESAKE! It’s our GENESIS! It’s horrible, I love it. Legend has it Joey King’s wig is still out there somewhere, lost, just waiting to be found.
Fletcher: This is kind of like Love, Simon for me; but they live in Southern California, so it really doesn’t feel like Fall. Back to school, and suddenly everyone’s in a relationship. There’s a Thanksgiving scene in the sequel, but they’re overlooking a sunny beach — cognitive dissonance.
