There's a Romcom for That, pt. 3
A guide to what to watch, why
Welcome to the third and final installment of “There’s a Romcom for That,” where I suggest a romcom for a season, a place, or a situation. Although, is is my final installment? By my count, I have only recommended 100 romcoms across all three guides, but my list has over 400 films on it…so we’ll see.
The first guide offered a month-by-month watch guide to the best romcoms. The second guide was based on setting, and has a world map to the best romcoms by country. (Both guides are linked just below.) The third guide, “What to Watch, Why” curates the best movies to watch for whichever hyper-specific situation you’re in.
As always, the same rules from the last guide apply, so if you missed that one, I’d recommend quickly skimming the intro. The tl:dr is A) I use the term romcom loosely, and B) I don’t put dates because everyone needs to stop being afraid of older movies.
There's a Romcom for That, pt. 1
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.Seriasly is a reader-supported publication. To receive new po…
There's a Romcom for That, pt. 2
Two weeks ago, I published the first part of my not-at-all-neurotic romcom guide, which is predicated on the belief that romcoms are meant to be watched situationally (for a time of year, as a postcard to a place, or to help you manage a sticky romantic situation).
What to watch, why…
If you’re done with the apps
An independent, 30-something, New York woman working in the literary world gets set up with a pickle seller when her bubby hires a matchmaker. A beautiful story about pride and humility and the Jewish culture of the Lower East Side.
(Another) independent, 30-something, straight, New York woman working in the *journalism* world decides to answer a personal ad in the women seeking women section.
I feel its problematic in how in deals with sexuality, but its a good story, overall.
Yet another independent, 30-something, New York woman working in the *travel* industry hires an escort as her date to her sister’s wedding in London.
Dermot Mulroney should star in every romcom, ever.
The movie that inspired You’ve Got Mail.
Two lonely people become penpals and fall in love in their letters, only they don’t realize they’re enemies in real life at the shop where they both work.
Jimmy Stewart has my heart, always.
Coming Soon: Materialists
I am SO excited for Materialists, which comes out this month in the U.S. but not until August in the U.K. 😭 This new film from Celine Song (Past Lives) is about an elite matchmaker, Dakota Johnson, who is caught between the Pedro Pascal and Chris Evans.
Their ad campaign has been masterful.
If you have a crush on Jack Schlossberg
The President of the United States falls in love with an environmental lobbyist.
They have a sleepover at Camp David.
Aaron Sorkin wrote this movie before going on to create West Wing and you’ll recognize some of the future WW cast.
A politician running for U.S. Senate falls for an employee of the hotel he’s staying at after she pretends to be a guest.
If you’re so in love, it makes you want to sing
This movie scared me as a child, but I rewatched it last year and completely fell in love with it.
I don’t know what a runner’s high feels like because I refuse to run, but I imagine it feels something like watching Julie Andrews dance through Vienna singing “I Have Confidence.”
I love movies about movies. Set during the advent of the “talkies,” a major movie star enlists a struggling actress to be the voice behind his shrill co-star.
If you’re blowing all your cash on weddings this summer
Maya Erskine and Jack Quaid are college friends who decide to attend every wedding together one summer in an attempt to save money. This might be one of the only fake relationship tropes that actually kind of makes sense?
Richard Curtis does it again: Hugh Grant and his band of oddball friends have a summer full of weddings.
I always think the romantic leads in Curtis’ movies are outshone by the friends, and this film is no exception.
If you love your sisters so much you wish you had two or three more
This needs no explanation.
“What excellent boiled potatoes.”
The romance of sisterhood far outpaces the actual romances of this movie.
If you want to cry so hard you feel like your eyeballs are going to fall out
Brittany Murphy is Molly, the daughter of a dead rockstar who has just lost her inheritance to an embezzlement scheme. To make ends meet, she takes a job as a nanny for stuck-up, Park Avenue Princess, Lorraine, played by Dakota Fanning. The two girls help each other heal.
Sisterhood of the Traveling Pants
Four childhood friends find a magic pair of pants just before they all split up for the summer. The pants are mailed around the world and inspire a summer of adventures.
I just watched this on the plane for nostalgia purposes and cried so much, I forgot that this movie is sneaky REALLY sad.
If you’re worried your crush won’t like you the way you are
Amanda Bynes plays a soccer superstar who’s team gets shut down at school. She goes undercover as her brother to play on the men’s team at her rival school.
I have watched this movie so many times that I once put it on 2x just to watch the whole thing and recite every line. (And to answer your question: no, I didn’t have friends in high school).
This is an adaptation of Shakespeare’s “Twelfth Night” and, if you’ve read all three romcom guides, you will know what I am going to say next: Shakespeare and Austen adaptations make the best romcoms.
A contemporary adaptation of “Cyrano de Bergerac”, Steve Martin plays a man with an abnormally large nose who falls in love with Roxanne, played by Darryl Hannah. Roxanne also captures the attention of a local firefighter, who enlists Martin’s help to write letters to Roxanne to woo her.
Hilary Duff (aka Queen of my Heart) has a secret penpalship with her high school’s football star, played by Chad Michael Murray. Can she keep their romance alive while keeping her identity a secret?
“Waiting for you is like waiting for rain in this drought.” I.CON.IC.
If you’re secretly in love with your best friend
Monica and Quincy are childhood best friends who both go on to become D1 basketball players for USC.
The movie is divided into four parts, and in each part we see Monica and Quincy struggle with their feelings for each other as they keep coming together and pulling apart like magnets throughout their lives.
Freddie Prinze, Jr. and Claire Forlani meet as children and instantly dislike each other. They keep bumping into each other until they finally reunite at UC Berkeley. Their friendship grows while they date other people until finally they realize they have feelings for one another.
The Y2K vibes of this movie are incredible.
If you need to switch up your Hot Priest fantasies
Ed Norton (with bleach blonde hair) and Ben Stiller are childhood best friends who grew up to become a priest and a rabbi, respectively. The third member of their childhood trio, Anna, visits them in New York and the men compete for her affection as they realize they both see her as more than a friend.
Kate Hudson has a fabulous life in New York…until her sister and brother-in-law die in a car accident and leave their three children in her care.
Aiden from Sex and the City plays her love interest and his character’s name is literally Pastor Dan.
If you aren’t afraid of a black & white movie
Often celebrated as the first talking-picture romcom, It Happened One Night is about an heiress running away from her father and a reporter trying to help her while simultaneously trying to scoop her.
This movie made its way to the silver screen just four months before the Hays Code went into effect, so it’s a bit spicier than you may expect (for the era).
I’ve written about The Philadelphia Story before, but as a refresher: it tells the story of Tracy Lord (Katherine Hepburn), a society girl, who is about to remarry. Just before her wedding, her ex-husband, Dexter (Cary Grant), shows up in town.
Jimmy Stewart also throws his hat into the ring to compete for Tracy’s affection.
There’s a remake with Grace Kelly & Frank Sinatra called High Society, but the original is best.
My friend Colin and I were recently discussing that this film is ripe for a remake.
Cary Grant stars in another movie where he tries to win back his ex-wife, played by Rosalind Russell. But this time it’s his ex-wife and star reporter, and he’s about to lose her in both roles if she gets married. He convinces her to do one more story with him as he attempts to get her back.
Russell’s role was originally written for a man, but while they changed the gender for the movie, they kept the name, Hildy, which I love.
If the timing’s not right
Before Sunrise / Before Sunset / Before Midnight
![Amazon.com: The Before Trilogy (Before Sunrise/Before Sunset/Before Midnight) (The Criterion Collection) [DVD] : Julie Delpy, Ethan Hawke, Richard Linklater: Movies & TV](https://substackcdn.com/image/fetch/$s_!Oy84!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9ea8318b-1f4a-402e-adf6-20ca6741afad_894x503.jpeg "Amazon.com: The Before Trilogy (Before Sunrise/Before Sunset/Before Midnight) (The Criterion Collection) [DVD] : Julie Delpy, Ethan Hawke, Richard Linklater: Movies & TV")
Before Sunrise: Celeste and Jessie meet on a train through Europe. Jessie convinces Celeste to get off early with him in Vienna and they spend the night wandering the city.
Before Sunset: Jessie has just released a book roughly based on his night with Celeste nine years before. Celeste attends his release event in Paris and they spend the afternoon, once again, wandering through the city.
Before Midnight: Another nine years have passed, and Celeste and Jessie are now married with twin girls. They are all on vacation in Greece and they spend one night just the two of them, reflecting on their relationship.
I’ll be honest, it took a while for me to warm to the Before Trilogy. I recently rewatched Before Sunset and, now that I’m in my 30s, it really resonated with me. These movies are mostly walking and talking, but the conversation is incredibly beautiful once you get used to the format.
If you’re feeling homesick
Set in the 1950s, Eilish (Saoirse Ronan) immigrates to New York from Ireland. She struggles to find her footing in the city, but then she meets Tony, the son of Italian immigrants. Her budding romance means that Brooklyn might become her forever home, and she travels back to Ireland once more as she tries to decide which path her life will take.
Tony’s adoration of Eilish always has me kicking my feet and giggling, no matter how many times I watch this movie.
Whenever I’m feeling homesick, I put this movie on the TV and pretend I live in Meryl Streep’s house.
If you believe age is just a number
Michelle Pfieffer is a television executive in LA. Paul Rudd is a struggling actor who gets cast on her show. He’s interested in her, but she resists his advances because of their sixteen-year age difference.
I feel like Paul Rudd just improvised this whole film.
The films a bit old school in terms of beauty and body standards, so you just have to take that with a grain of salt.
Sabrina (Audrey Hepburn) is the daughter of the chauffeur to a very wealthy New York family. She’s in love with the younger of the two sons, but he fails to notice her. But after she moves to Paris and becomes a W.O.M.A.N., he finally pays her attention. So much attention, in fact, that the family deems her a threat and tries to throw obstacles in her way. Humphrey Bogart, the older of the two brothers, is one of these obstacles.
I totally understand why Bacall married Bogie.
If you’re having marital issues
Pitt and Jolie are a pair of married assassins. One day, they both receive the same assignment: kill their spouse.
Catherine Zeta-Jones is a notorious gold digger, George Clooney is the divorce lawyer trying to take her down.
I love the Coen brothers. Highly, highly recommend this one.
Three college friends are reunited after the fourth member of their clique commits suicide after her ex-husband marries a younger woman. The three remaining friends, Goldie Hawn, Diane Keaton, and Bette Midler, decide to take revenge on all of their ex-husbands.
If you’re stuck in a rut
Nyles and Sarah get sucked into a timeloop in the California desert. Nyles accepts his fate and makes the most of the experience, while Sarah fights to escape.
Cooper Raiff writes, directs, and stars in this movie about a young man who moves home after graduation without a job. He trips into a job as a bar/bat mitzvah party starter and meets Dakota Johnson, who is a mom of one of the middle schoolers at the parties.
If you love Babs like I do
Barbra Streisand plays Fanny Brice, a real life vaudeville comedian, and the movie traces her career. She falls in love with gambling bad boy Nicky Arnstein (🎶 Nicky Arnstein, Nicky Arnstein, what a beautiful, beautiful name 🎶).
As you may have heard, I have a huge crush on Omar Sharif
It’s physically impossible not to belt out “Don’t Rain on My Parade” when Babs starts singing
The screwiest screwball comedy. Streisand plays Judy Maxwell, a lifelong student who still hasn’t decided on a life path. Ryan O’Neill plays Dr. Howard Bannister, a geologist. The hilarious Madeleine Kahn is his fiancé. The trio accidentally gets mixed up in a heist gone wrong.
This movie showcases Babs’ more dramatic side. She plays Katie (Ka-ka-ka-katie) who falls in love with Hubbell (Robert Redford) but the two are polar opposites: she’s a jewish activist and he’s an apathetic WASP. They meet again after WWII and fall in love, but their opposing personalities and dreams threaten their relationship.
If you want to go back to school
The titular wild child, Penny (Emma Roberts), gets sent to an all-girls British boarding school as punishment. She rails against the system but ends up making lifelong friends and even finding romance along the way.
A young Rooney Mara stars in this movie, also about an all-girls boarding school. This movie is darker than Wild Child, but it’s set in fall in New England so it’s perfect back to school vibes.
And finally, if you want to watch something really, really bad (aka if you’re hungover on your couch or on a really long plane ride)
Kirk, who is a “5”, accidentally wins over Molly, who is a “10”. This movie is incredibly stupid, but I always end up rooting for the two romantic leads to get over their obsession with societal perception/expectations and get together. Also it’s just really funny and my sisters and I quote it all the time.
The premise of this movie is BAD. Basically, it presents an idea that each friend group has a DUFF (designated ugly fat friend). See? REALLY BAD. But I love Mae Whitman and in her character’s quest to overcome her “DUFF” identity, she comes out of her shell and becomes more comfortable with her true self.
You think your long distance relationship is hard? Try being separated by two years. Sandra Bullock and Keanu Reeves own the same house, but they own it two years apart. The mailbox is magic and can transport their letters through time. I don’t think I need to say anything else.
One thing about me is I will do anything for Keanu Reeves, including watch this movie.
In fact…I’ll just let Keanu Reeves have the last word of the official romcom guide:
No she’s the man quote??