Happy love month everyone! As a certified lover girl, I adore Valentine’s Day in all its cheesy, capitalistic glory. Was it created to sell chocolate, flowers, teddy bears, and greeting cards? Maybe so. Does it peddle surface-level declarations of love without regard for what actual love looks and feels like? Probably. Do some people go overboard and put too much pressure on themselves to celebrate? Definitely. But at the end of the day, it feels nice to have a day to celebrate romance.
However, as a certified single girl, I don’t have any reason to celebrate other than going out with my girls on Galentine’s Day, an unofficial holiday created by certified girl’s girl Leslie Knope of Parks and Recreation that has since taken the real world by storm. So to fill the void that lack of romance has left in me, I watch romance films that require no emotional effort on my part other than rooting for two people to get together in very unrealistic, low-stakes situations. This is where rom-coms come in. Over my 27 years, I’ve seen and loved quite a few. These 5 are the ones I have a deep attachment to.
1. Sleepless in Seattle (1993) dir. Nora Ephron
Sleepless in Seattle is one of the first romance films I was ever exposed to (my family liked Tom Hanks and watched anything he was in). I can’t begin to describe the feelings of comfort and hope for love that consume me when I put it on. ‘Sleepless’ follows recently engaged journalist Annie (Meg Ryan) and recently widowed architect Sam (Tom Hanks). One night, Sam’s son Jonah calls a radio show to tell them about how lonely his father is. Jonah convinces Sam to talk to the show’s host about how much he misses his wife. During a drive to visit her fiancé, Annie hears Sam on the radio and is deeply touched by his story. Annie, who feels like something is missing in her relationship, writes to Sam, asking him to meet her on the top of the Empire State Building on Valentine’s Day. Annie decides against sending it until her editor at her newspaper sees it, mails it for her, and sends Annie on assignment to Seattle where Sam is located so that Annie can get a look at him. Meanwhile, Sam’s newfound fame attracts many women to him and he begins dating. He gets Annie’s letter but is unconvinced to go meet her. Jonah, however, thinks Annie is the one for his dad and answers. I’ll save the rest of the plot for you to find out but I’m sure you can guess where it ends. Nobody does rom-coms like Nora Ephron and I hope we as a society get back to a point where films like this can be made in earnest, with big budgets and wide theatrical releases instead of being dumped on streaming services.
“Destiny is something that we’ve invented because we can’t stand the fact that everything that happens is accidental.”
2. Roman Holiday (1953) dir. William Wyler
It’s always “wyd” and never “You don’t know how delighted I am to meet you.” Old Hollywood romance films are an era we’ll never return to, for better and for worse. One of my favorites from the era is Roman Holiday, Audrey Hepburn’s debut in a major American film role. Hepburn plays Ann, a crown princess who is on a tour of European capital cities on behalf of her country. After breaking down due to the stress of her every moment being watched and scheduled, Princess Ann disguises herself and explores Rome, ignoring all of her duties. Ann is found asleep by Joe (played by Golden Age hottie Gregory Peck), an American reporter who doesn’t recognize her. Earlier, a doctor had given Ann some drugs for her stress, which is what made her fall asleep. The effect of the drugs makes Joe think she’s intoxicated, so he takes her back to his apartment where she can safely sleep the drugs off–and that’s how you know this film is utter fantasy. Joe blows off a press conference that Ann was also supposed to be at and when his editor finds out, Joe identifies the woman in his apartment as Princess Ann and says he can get an exclusive story with her. Joe takes Ann around Rome for a day trying to get the story without letting her know he’s a reporter. I love the film for many reasons, mostly Audrey Hepburn, but many scenes were actually filmed in Rome, so I love getting to view the city in such a different time and fantasize about having my own Roman holiday, with or without the love interest.
Ann: I have to leave you now. I'm going to that corner there and turn. You must stay in the car and drive away. Promise not to watch me go beyond the corner. Just drive away and leave me as I leave you.
Joe: All right.
Ann: I don't know how to say goodbye. I can't think of any words.
Joe: Don't try.
3. What If (2013) dir. Michael Dowse
Back in 2013, Harry Potter was still recently over (ish), so Daniel Radcliffe was throwing himself into projects of all kinds and one of them was the romantic comedy What If. The film follows Wallace (Radcliffe), a medical school dropout suffering from heartbreak after catching his girlfriend cheating. Wallace’s best friend Allan (Adam Driver) convinces him to attend his party and start trying to be social again. At the party, he meets Allan’s cousin Chantry (Zoe Kazan), a kind and quirky animator, and they hit it off. Wallace walks Chantry home and thinks this might be his chance at romance–until Chantry mentions her boyfriend. Later, Wallace has a chance meeting with Chantry at a screening of The Princess Bride and Wallace decides being Chantry’s friend is better than not knowing her at all. But as they grow closer, Wallace can’t deny his feelings for Chantry and things get complicated. Meanwhile, Allan meets the love of his life at his party, his love life aligning perfectly alongside the trainwreck that is Wallace’s, making for a hilarious juxtaposition. I will forever be obnoxiously proud of the fact that I didn’t discover Adam Driver from Girls, Star Wars, or A Marriage Story but rather his role as the best friend of Daniel Radcliffe in a movie that practically nobody watched. The movie tries to update the question of “Can men and women be friends without sex getting in the way?” a la When Harry Met Sally. It doesn’t really do anything differently with it other than establishing Wallace’s romantic feelings from the start. But it’s still a really cute and charming movie, and Radcliffe and Kazan work well as romantic leads. Another thing I love about the film is that it’s set in Toronto and was filmed there, so there are beautiful shots of the city.
“In fairy tales, love inspires you to be noble and courageous. But in real life, love is just an all-purpose excuse for selfish behavior.”
4. 27 Dresses (2008) dir. Anne Fletcher
Being a 12-year-old girl with an obsession for NYC in 2008, 27 Dresses was bound to attach itself to me. The film follows Jane (Katherine Heigl), a young professional in NYC who has been a bridesmaid 27 times and can only dream of the day she will finally be the bride. On one particular night, she is a bridesmaid in 2 weddings that are happening simultaneously, so she’s running back and forth between them the whole night without anyone noticing. One person who does notice is Kevin (James Marsden). The two meet and instantly dislike each other because Jane thinks Kevin is too cynical and Kevin thinks Jane is too uptight, but they have cute, flirty banter. After sharing a cab home, Jane leaves her day planner behind and Kevin takes it, using it as an excuse to see her again. Meanwhile, Jane’s younger sister Tess comes back from Europe and falls in love with Jane’s boss George, which is devastating for Jane because she’s in love with him despite Wonder Bread being more interesting than he is. Their whirlwind romance results in them getting engaged and now Jane has to plan the wedding. Tess and George’s wedding will be in the paper, so the two of them and Jane meet the reporter covering it, and lo and behold, the reporter is Kevin! Kevin, now aware of Jane’s side hustle as a bridesmaid, uses this as an excuse to secretly write an article about Jane to pursue a more serious journalism career but starts falling for her. And now I’m realizing that most of my picks for this list involve journalists and deception. If anything, this movie SHOULD have been the jumping-off point for James Marsden to become a leading rom-com man, but I guess we just can’t have nice things. Jury Duty was great, though.
Kevin [trying to get Jane to be more firm with her boundaries]: “What about you? You don’t have any needs?”
Jane [deadpan]: “No. I’m Jesus.”
5. 10 Things I Hate About You (1999) dir. Gil Junger
The teen rom-com to end all teen rom-coms. This movie built me. It’s a part of my very core. Every man I date must pass the 10 Things I Hate About You test. What is the test? I’m not sure exactly, I think they just have to watch it and like it. A modern adaptation of Shakespeare’s The Taming of the Shrew, the film follows riot girl Kat (Julia Stiles) and her popular younger sister Bianca. A new kid at school Cameron (Joseph Gordon-Levitt) falls in love with Bianca at first sight but Michael (David Krumholtz) informs him of the well-known rule for the sisters: their paranoid OB/GYN father doesn’t allow them to date because he’s delivered one too many babies to teen moms. Frustrated by this rule because she wants to date popular model Joey, Bianca convinces their father to let the sisters date, but there’s a catch: Bianca can only date when Kat does, and this is unlikely since Kat is a social outcast. Informed of this new rule, Cameron devises a plan: he will convince the school’s local bad boy Patrick (Heath Ledger) to date Kat. But his initial attempts don’t go well, so to motivate Patrick, Cameron convinces Joey to pay Patrick to date Kat, telling Joey that doing so will allow Joey to date Bianca, meanwhile, Cameron will use the opportunity to pursue Bianca without Joey finding out. It’s really a lot less confusing than it seems. Of course, Patrick starts having real feelings for Kat and does things to win her over like serenading her with a full band on the school’s football field. Sigh. Men today just like your Instagram story. The movie is hilarious, the 90s fashion is perfect, Heath Ledger is the man of my dreams, Gabrielle Union is also in it, and they really just don’t make them like this anymore! Part of my rebellious girl streak was due in part to Kat and she remains one of my favorite characters ever to this day.
“Hello, Katarina. Make anyone cry today?”
“No, but it’s only 4:30.”
LOVE MONTH ON MARY’S NEWSLETTER:
February 1st: “5 rom-coms I can’t live without”
February 8th: “I still can’t listen to harry styles”
February 15th: “the intimacy of sharing a meal”
February 22nd: “my experience of physical touch as told through Edward Scissorhands”
Have you seen any of the films on this list? What are some of your favorite rom-coms? Do you have any Valentine’s Day plans? Let me know in the comments!
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I know everyone has left a comment about it but 10 Things I Hate About You really shaped me TO MY VERY CORE. I am, and always will be, in love with Heath Ledger because of that movie. I also wanted so badly to be like Kat as a teen that I still catch myself listening to certain songs and buying those long skirts she always wore, unconsciously trying to be like her. I am the way I am because of Kat Stratford. lol
But also What If? unlocked a DEEP memory for me. Holy shit. I remember seeing the trailers for that movie and wanting to see it soooooo bad and then I completely forgot about it until this very moment. New goal in life: finally watch What If? and fulfill my pre-teen dreams.
YOU NAILED IT, 10 Things I Hate About You is such a classic love story and my comfort movie (Heath Ledger. Right? Phew).
I rly enjoyed 27 Dresses growing up but haven’t seen it years, maybe I’m due for a rewatch