There's a Romcom for That, pt. 1
A guide to what to watch, when
This post became very long, very fast, so I had to split it into three parts. This first post is dedicated to romcoms organized by season.
This is not a ranking of romcoms. There are one million romcom rankings online and most of them have got it all wrong. Romcoms aren’t meant to be watched in order of how good they are. Some of the best romcoms are god-awful. I propose, instead, that romcoms are meant to be watched situationally.
More specifically, they are meant to be watched in anticipation of a situation. For example: it’s the last week of August, the air has the faintest hint of that tell-tale crispness, its time to watch You’ve Got Mail and wriggle in your seat when the Cranberries start singing about Dreams and Tom Hanks starts extolling the rites of Fall — “bouquets of freshly-sharpened pencils.”
Or, your trip to Paris is weeks away and you turn on Midnight in Paris to soak in the sights at the Rodin Museum and Marché aux Puces through that golden hour filter before you go.
OR, you’re starting to wonder if you might have feelings for your friend…but what if moving it in a romantic direction ruins things? You’ll have to watch Love & Basketball to be reminded that going from friends to lovers isn’t always a linear path, but that doesn’t mean you shouldn’t try.
Romcoms are stories of anticipation. They explore the lead-up to a life-changing romantic event. Romcoms rarely ever show the realization of the main characters making their lives together; more often than not they end with a first kiss or a proposal.
And so, whenever a particular situation arises in my life, I prescribe myself a romcom to watch like medicine. And I prescribe them for my friends, too. But I’ve seen a lot of romcoms, and it has become difficult to keep track of all the Rx papers I’ve handed out over the years. So, during Covid I did what any sane person would do: I made a spreadsheet to organize my romcom rewatch system.
This three-part series of romcom guides will layout what to watch for each scenario. First up, a month by month calendar of my annual romcom rewatches to welcome a new season or holiday.
On a scale of Rom to Com
This list includes a lot of movies that many may not consider romcoms. I use the term “romcom” to signal the vibe of how a movie makes me feel instead of fitting it to a genre. Even when you search romcoms on Google, the list that the search engine compiles is vast and varied, with few picks fitting squarely into the definition. I rank romcoms on a scale of rom (1) to com (10). Anything ranked 5 is a true romcom, a blend of both emotions. For example: I consider 10 Things I Hate About You to be a solid 5; a true romcom.
One more note: I wont be putting years next to these romcoms (unless they are a remake) because some people out here are complaining about lack of quality romcoms in the last few years but also refusing to watch a movie more than 15 years old. You have no idea what you’re missing. Also, film is beautiful and HD is horrifying. Okay, rant over.
What to watch, when…
*Asterisks indicate holiday-specific movies.
January
Ashton Kutcher and Amanda Peet keep bumping into each other over ten years, but the timing is always wrong. This is one of my favorite romcoms ever, and not nearly enough people have watched it.
The perfect New Year’s kiss (sorry Billy Crystal).
Ashton Kutcher’s butt cheeks.
Workaholic consultant Diane Keaton inherits a baby, buys a farm in Vermont, and falls in love with a vet (played by the ever-charming Sam Shepard, whom Joni Mitchell wrote Coyote about).
February
Sleepless in Seattle* & An Affair to Remember*
Sleepless in Seattle is loosely inspired by An Affair to Remember and both feature a promise to meet at the top of the empire state building on Valentines Day. Also Sleepless in Seattle has some of the mushiest lines which are perfect for the mushiest holiday:
“I knew it the first time I touched her. It was like coming home, only to no home I'd ever known. I was just taking her hand to help her out of a car and I knew it.” - Tom Hanks as Sam Baldwin
If you only watch this movie once every four years that would be enough.
March/April
Picnics in the English countryside, trees in bloom, b*tchy little hats; this is Jane Austen’s spring. The 1996 version is dreamier, the 2020 version is funnier (Autumn de Wilde is the only director that I think actually gets Jane Austen).
May/June
Summer storms, midnight pancakes, and Keanu Reeves at a farmer’s market.
Jack Nicholson’s butt cheeks.
July
This is THE summer movie.
A modern-day Pride & Prejudice on Fire Island, Long Island’s idyllic queer summer community.
August
We all know this one, we all love this one. I’m ignoring the fact that everyone’s favorite DILF is now a Trump supporter.
During the last few weeks before starting college, a girl meets her future self during a mushroom trip. Her future self inspires her to stop taking the life she’s about to leave behind for granted.
A new contender, and a strong contender, for end of summer/back to school vibes.
September
*I am counting first day of Fall as an official holiday.
As previously mentioned, please see soliloquy on Autumn that opens the movie.
October
Kicking fallen leaves in Central Park while wearing the perfect fisherman sweater.
I used to have an annual watch party to celebrate Fall, and I would make a risotto with squash and sage and all kinds of autumnal flavors.
For the record: If someone tells me one more time that they found When Harry Met Sally… cliché…YOU CAN’T BE THE CLICHÉ IF YOU INVENTED THE CLICHÉ! Do your research and then talk to me.
Michelle Pfieffer is a single mom. George Clooney is a single dad. They hate each other. He carries her through a puddle in Central Park.
Sandra Bullock and Nicole Kidman are witches and sisters trying to break their family’s curse. Incidentally, Nicole Kidman sports the most perfect cut and color in the history of hair in this movie.
November
He’s a hockey-playing preppy Harvard boy who’s had everything handed to him, she’s a brainy, musical Radcliffe girl with a chip on her shoulder.
Watch it for Ali MacGraw’s perfect Fall style.
The theme song never fails to make me cry.
Bonus Points: listen to The Kid Stays in the Picture audiobook by Bob Evans for his account of making Love Story and falling in love with Ali MacGraw in the process.
December
There are too many Christmas movies to list here, but this is the one that I will actually get mad over if my family watches it without me.
Nothing says Christmas like a fight between a huge dysfunctional family at the dinner table (and strata).
This film begins and ends at Christmas. Also, in the canon of sequel movies, they’ve done a pretty good job of keeping consistency without feeling stagnant, every sequel is worth a watch. But the OG is for every Christmas.
Sometimes romcoms have a plot so absurd that you have to just go with it: Sandra Bullock saves her crush from death on the train tracks in Chicago and when he comes to in the hospital with amnesia there is a mixup and everyone thinks she is his fiancé, including him. His family welcomes her home for Christmas while he recovers in the hospital, and Bullock ends up falling for his brother instead.
Bill Pullman is one of my favorite romcom leads of all time (I’m waiting for his son, Lewis, to fill his shoes)
Watch out for the next part of this series: what to watch, where. We’ll take a world tour of romcoms.
A sneak preview: does anyone know what movie this is from/where it’s set?
Thanks for reading, and if you want to catch the next guide then…
Amazing!! So many movies I haven’t seen on this list and I can’t wait to watch them! Thank you!
I am expecting “Comrades, Almost a Love Story” for HK next week. If it’s not there, I will be disappointed.