9: How to Lose a Guy in 10 Days
Before we get into it, I just want to start off by saying that the best way to describe this film is by a very specific color between orange and yellow. How to Lose a Guy in 10 Days is a classic romcom directed by Donald Petrie and based on the book written by Michele Alexander and Jeannie Long.
The film starts with a journalist named Andie Anderson—portrayed by Kate Hudson—who writes for a magazine that’s too focused on the chattier aspects of life to appreciate Andie’s articles on statistics and logic. In order to get further in the world of journalism, she hatches a social experiment that is composed of both fact and gossip. She plans to catch a guy and lose him within ten days after pulling a number of common mistakes that many women supposedly make when trying to find the love of their life.
Following Andie’s pursuit, we find that Benjamin Barry—played by Matthew McConaughey—also formed a bet with his boss, claiming that he could make any woman fall in love with him within the next ten days in order to prove that he can market himself well to women and effectively persuade them into buying his products. The classic workings of a businessman: manipulation.
Anyone can guess where the story is headed from here. The situations that the characters are put in are admittedly hilarious, and director Donald Petrie clearly refused to fall short on putting the comedy in romcom. In fact, How to lose a Guy in 10 Days is the kind of film where you physically cannot like either character more than the other because neither of them is particularly right enough to be favorable. Both characters are not inherently special or in any way all that complex, but they’re ditzy, entertaining, and cliché. The movie was hard-hitting on comedy and comfort, but the romance was pretty lost in translation between all the skits.
If you’re looking for a complex heart-to-heart this Valentine’s Day, this one is not for you. Even so, the film is definitely worth watching when it comes to sharing a good laugh with your loved one and maintaining good vibes all around.
8: Howl’s Moving Castle
Howl’s Moving Castle is an animated film produced by Studio Ghibli and fabricated by Hayao Miyazaki. The movie was adapted from the English book written by Diana Wynne Jones in 1986. The story follows a young lady named Sophie who believes she is too ugly to be kidnapped by a heart-stealing wizard named Howl, who lives in–you guessed it–a moving castle.
Following the English dub, Howl is voiced by the famous actor Christian Bale. So it’s pretty understandable when it’s revealed to the audience that Howl is a desirable character and portrayed as attractive, contrary to how Sophie feels about herself. When the cruel Witch of the Waste curses Sophie to turn into an old woman, Sophie runs away and decides to become a cleaning lady for Howl in his moving castle.
The film explores ideas of vanity, the portrayal of beauty, and most importantly, love. The romance between Howl and Sophie is completely transparent, which might actually be a little off-putting, considering Sophie is an old lady when the chemistry between them starts. The first time watching the film, the audience might be left a little confused, especially if they weren’t paying attention. The thing about most Studio Ghibli films is that in order to fully immerse yourself in the storyline, you have to let go of a piece of the reality that you know to be true and keep an open mind so that all of the new logic that makes sense in this world makes sense.
Howl’s Moving Castle is most definitely a film that you need to watch twice in order to fully understand it. The beautiful animation, the comforting music playing, and the whimsy throughout the film make it easy for the viewer to immediately get hooked, even if the conclusion of events is a bit too far gone. The easy-going pacing of the film, on top of the well-developed romance, is what makes this film so enjoyable. This is another movie that allows for sitting back and relaxing and is definitely worth the one or two rewatches to spend with your partner this Valentine’s Day.
7: Enchanted
Moving along from a sense of calm, now it’s time to try nostalgic chaos. Enchanted is a film produced by Walt Disney Pictures, written by Bill Kelly, and directed by Kevin Lima. The story opens with an animated Giselle, starring Amy Adams, singing a melody about longing for her Prince Charming–most of all, her true love’s kiss. However, she is thrown out of the world of animation through an enchanted well, only to crawl out of a not-so-enchanted sewer system into the infamous New York City.
Finding herself in a foreign land, she finds herself living with a logical divorce lawyer named Robert Philip, played by Patrick Dempsey. Of course, Giselle is completely oblivious to the idea of divorce, let alone any sense of logistics outside of singing squirrels and busy birds. Robert is meant to be the responsible adult who gives Giselle a new perspective on how life can be once she separates herself from the expectations of happy endings and silly love songs. Even so, Giselle is also meant to be the chaotic factor in Robert’s life that shows him excitement and the spontaneity of what romance should look like.
Both characters are the exaggerated extreme of two sides of the same spectrum: extreme chaos and extreme control. Too much of anything is never good, and this film really puts into perspective how the fairy tales you grew up hearing about can still teach lessons about how romance can be spontaneous and outlandish, even in the most serious of situations. You can pay bills and stress about work, but it’s never a good idea to forget the whimsy of life, as long as you remember your responsibilities as well.
While it may not be the best romcom of all time, it’s definitely a worthy choice to spend February 14th with. The classic trope of seemingly opposite people finding love and somehow making it work is always a good choice to make. Enchanted uncovers the true meaning of how mediums and compromises are important aspects to making a relationship work. These lessons paired with the comedy and chaotic contradictions of fairy tale and tedium? What’s not to like?
6: 50 First Dates
What good is a romcom if the writing falls short on either romance or comedy? Everyone knows that Adam Sandler has always been a comedic man; that is just a fact. But who would have thought that he was also quite the romantic? Sure, he’s had other romances like Just Go With It, for instance, but this is by far the best one.
50 First Dates tells the tale of a forgetful Lucy Whitmore–though forgetful might be quite the heavy understatement. Lucy is portrayed by the lovely Drew Barrymore, while our male protagonist is none other than the funny man himself, Adam Sandler. Lucy Whitmore has a brain condition that hinders her short-term memory, and thus, she cannot live past the day she got into a gruesome car accident. Since she cannot process any new information and lives in a constant loop, she can not remember Henry after any of the instances she “first” met him. Henry, being the dedicated man that he is, takes it upon himself to meet her every day and have her fall in love with him again every single day so they can go on their first date fifty different times.
This film reveals the true dedication and loyalty that love comes with. It shows true devotion and creativity inspired by love. There are a number of instances where the audience has the chance to take a step back and think “Woah. He has to do this everyday for the rest of his life if he truly intends on marrying this girl. Is it even worth it?” Then a heartfelt montage scene between the couple follows and the viewer remembers “Oh right, he loves her”.
While the romcom in itself is hilarious and outlandishly bizarre, the depth of the story is never lost. It’s a perfect conversation starter to have with your partner. Are they willing to convince you to fall in love with them every single day, even if they knew you would forget about everything the next day? Are they even your valentine if they wouldn’t treat every day as Valentine’s Day?
5: Eternal Sunshine of the Spotless Mind
Regardless of what you’ve heard about this movie, I’m convinced that it’s the perfect relationship movie to watch with your partner. Is it a romance? That’s debatable.
Eternal Sunshine of the Spotless Mind was a film directed by Michael Gondry and written by Charlie Kaufman that was meant as a message to people that sometimes relationships are just bad. Sometimes they don’t last, no matter how hard you try to make it work and that’s okay because the experience is always worth more than the outcome.
Our two protagonists are Joel, played by Jim Carrey, and Clementine, played by Kate Winslet. Joel is an introverted individual who appreciates the quieter things in life, while Clementine is the complete opposite. She is a flamboyant and opinionated person who admittedly gets bored with staying in one spot for too long. They are in an on-again, off-again relationship that’s been going on for quite a while. Until Clementine goes through a memory wiping process that causes her to lose all memory of Joel and move on with her life. Joel, upon finding this out, does the same.
This is yet another case of how opposites attract, just like Enchanted. The understanding that has to be made in both films, however, is that the trop doesn’t always win. Again, the message that is being conveyed here is that the experience and happiness that you have with someone is always worth the pain, time, and effort it takes to move on.
This movie is definitely the outlier on this list, having focused more on thought-provoking character development than giggles. A lot of people think that light-hearted romcoms are the perfect vibes to go for when trying for a classic Valentine’s Day. However, I find that films that stir up deeper emotions are actually worth more of your time than watching any other movie that could be saved for lively up a lazy Sunday. It’s films like this that can actually make or break a relationship, and I think that’s worth something.
4: Gnomeo & Juliet
Switching gears a bit, now we have Gnomeo & Juliet produced by Elton John’s Rocket Pictures in a collaboration with Starz Animation. This film is a sillier adaptation of Shakespeare’s well-known Romeo and Juliet, directed by the creative Kelly Asbury.
The story follows the same trope as the classic play, if not in more detail. Gnomeo is voiced by the dazzling James McAvoy and Juliet by the eloquent Emily Blunt. The factor that keeps the two from being in love is the different lawns they come from. Gnomeo comes from a blue-themed lawn and Juliet from a red one. What started out as a pursuit of a majestic flower turned into the beginning of a forbidden romance.
This hilarious and immature conversion of the original still manages to push forth the star-crossed lovers trope, even if mostly censored by parental guidelines. The audience can still see the romance bloom between the two garden gnomes. From the catchy songs to the colorful animation, this is a film meant to be enjoyed by all ages, not just the kids. What makes this movie special is that while the romance montages are based mostly on chaos, the love is still real. I would even argue that the love between Gnomeo and Juliet is more genuine and realistic than the love between Romeo and Juliet. For a kid’s movie about garden gnomes to be both hilarious and more realistic than a classic that gets all the love, Gnomeo & Juliet is a gem.
I think we can all agree that the number of renditions that managed to be better than the original isn’t many. But surprisingly enough, Gnomeo & Juliet is definitely the exception. It has the perfect blend of obnoxious and genuine, which again is very impressive for a kids’ film. So if you’re looking for a laugh and an unserious movie to put on TV this Valentine’s Day, you and your partner would be surprised by how fulfilled you will feel finishing this one.
3: 13 Going on 30
13 Going on 30 is yet another one of the more classic romantic comedies with its perfect sense of 80s nostalgia in a very 2000s setting. It’s like the cinematography of every corner was meant to be aesthetically pleasing to the decade-era lovers. This film was written by Josh Goldsmith and Cathy Yuspa and directed by Gary Winick. Our main lovebirds were played by beloved Mark Ruffalo and Jennifer Garner as Matt Flamhaff and Jenna Rink.
Like every excited teenage girl, Jenna Rink is a girl who just turned thirteen and wants nothing more than to be thirty, flirty, and thriving. After a birthday-gone-wrong, she locks herself into her closet and magic glitter dust from her dollhouse turns her into a thriving and flirty thirty-year-old magazine editor in New York. In this time period, she got everything she wanted at thirteen. She was cool in school, she got a boyfriend, and she has money. However, she finds that having everything you desire as a naive teenager is not all that it’s cut out to be in the long run.
The relationship between Jenna and Matty started when they were childhood best friends. However, since Jenna got everything she wanted, she drifted away from Matty in the time she skipped over from when she went from thirteen to thirty. When she finds herself in an adult body, the first person she wants to find is her best friend and that is exactly what she does. This is where the story starts for them. The tale is up and down, and in this rollercoaster, the audience can see how the childlike wonder emitting from Jenna will rub off on Matt and show him that love can be fun and silly.
But outside of the love between them, the film also dives into Jenna’s relationship with womanhood as well as girlhood. Throughout the movie, our thirty-year-old protagonist sparks a friendship with a young girl who lives in her apartment building. To Jenna, she’s simply talking to another girl her age. To us, it reveals the relationship between a grown woman and a younger version of herself. The movie really is about how important it is to connect with all the parts of yourself, being both the young, the old, and the present.
On the downside of things, the film is about a thirteen-year-old girl in a thirty-year-old’s body. So the jokes get weird, which makes certain aspects of the film uncomfortable for the viewers to turn a blind eye to. For example, there’s a moment where Jenna is gossiping about a boy looking cute and how she’s nervous to go up to him. Her friend encourages her, so Jenna stands up to make her way over to the boy. Creepily, she passes the man who’s visibly her age and instead stops to make conversation with a little boy. In hindsight, sure, she’s a thirteen-year-old girl herself so obviously she would have differing preferences. But to visually portray a situation as uncomfortable as that purely for the sake of comedy is always more than off-putting. Luckily enough, the jokes aren’t all that persistent, but they’re still lingeringly perverted.
Putting that fact aside, the movie is also a classic and the vibes are expectantly upbeat and the definition of coming-of-age. Literally. Definitely worth the watch with the acknowledgement of criticism.
2: The Princess Bride
Most of us can agree that the number of boyish romance movies that still have the perfect amount of comfort is few, let alone boyish period dramas that are actually centered around romance. The Princess Bride is a film that completely blows any of its competition out of the water. Many will argue that it is simply the best romance movie out there and I would definitely find this opinion to be more than valid. It does not just focus on comedy and romance, but also on adventure and plot twists.
The Princess Bride was directed and co-produced by Rob Reiner, while the screenplay was written by William Goldman. The tale unravels a love between a farmboy and a commoner, farmer Westley played by Cary Elwes and a common girl–anticipated princess–Buttercup played by Robin Wright. It does not start with much of a slow burn or story, just a short recap of how these two came to be. After the farmboy leaves for riches, he is said to be murdered by a notorious Dread Pirate Roberts. Later on in the film, the audience, as well as Buttercup, finds this to be untrue. Wesley was consistently faithful to Buttercup even at the start of the story, replying to every one of her meager requests with an obedient “as you wish”. However, not much of Buttercup’s faith is so direct as she learns to have faith in their love gradually throughout the tale. The message meant to be had from their matured romance is that one should always have faith in love and in its power to bring souls together, even in death.
To dive further, this film not only analyzes the faith you are meant to have in your lover, but also the faith you are meant to have in yourself. A particular character that I find the most intriguing is Mandy Patikan playing Inigo Montoya. Throughout the film, Montoya stays faithful to his promise that he made to himself on finding his father’s killer, even going so far as to continuously rehearse the lines he would deliver to his nemesis once he found him. This versatile film was able to analyze the aspects of faith in not just two people, but also faith in yourself and your ability to keep the promises you make, no matter to whom you made them. It shows a true display of honor and how important it is to hold true to your words. I think this is such an important message to give an audience since it shows that you don’t need two people to have faith, you just need yourself.
When discussing the target audience, I think it’s important to note that the actual tale the movie is about is being told by a grandfather who wishes to read a childhood favorite to his sick grandson. The grandson at first is grossed out by the idea of listening to stories about romance and kisses, so he asks his grandfather to skip out on those parts. As the story goes on, the boy slowly gets more invested in the adventure that the plot follows, and henceforth grows fascinated with the strong love shared between Buttercup and Wesley. Once the story is over, his grandfather automatically skips over the final kiss to end the bedtime story and the grandson instead requests that he read it to the end. Not only did Princess Bride take extra care in building the development between each character in the tale, but it also went the extra step to show how the audience was meant to be impacted by the series of events themselves.
Personally, I think that it’s so satisfying to watch a movie without a constant underlying trope of girls being into romances and kisses while the boys are into cars and heroes. The boyish feel of the movie that was meant to be a romance is just so refreshing to watch play out and, instead, the underlying point in every scene is meant to be inclusive. I definitely think this is one of the more necessary films to watch during Valentine’s Day and it would be a shame not to. Everyone deserves to watch this film at least five times.
1: Flipped
Finally, we have the main course most deserving of the “Best Romance” Award. Flipped, another banger directed by Rob Reiner, after being inspired by the novel written by Wendelin Van Draanen. I mean, are we really shocked Rob Reiner had his hands on the top two movies on this list?
This is a narrative that follows the account of two perspectives in the beloved trope “she fell first, he fell harder”. It starts off from the very beginning with Morgan Lily acting as the young Juli Baker and Ryan Ketzner starring as Bryce Loski. Juli has a crush on Bryce that starts from the very first time she meets him and continues to fester as they grow up. Contrary to how Juli feels about Bryce, Bryce clearly has a worse perception of her than she does of him. Bryce moves into a new neighborhood and his neighbor–who lives across the street–is portrayed in his perspective as a crazy, lovesick girl who won’t get off his back.
In the first half of the movie, Juli stays true to her feelings no matter how intense they fluctuate with each event that goes on throughout her life. Despite her having a crush on Bryce, she does not let that blind her when he treats her badly, and she still cares about things other than boys. Which I definitely appreciate since a lot of media attempting to accurately represent a teenage girl with a crush on a boy often mistakes that infatuation for their center of attention. Yes, while girls often fixate on crushes, it’s not all that we care about. It’s so refreshing to see a young girl written as a dynamic character and not just a ditzy boy-crazy kid. She is a character who has loud opinions and things to stand up for. She’s interesting and not in a manic pixie dream girl way to appeal to her male love interest.
Ironically enough, there isn’t much about Bryce Loski that does not seem to center around Juli Baker. Even if a lot of his dialogue and character development is centered around a girl, he naturally has depth and interesting parallels to compare with his picture-perfect family to Juli’s not-so-picture-perfect family. The most depth Bryce has is centered around the dynamics of his family. His father is a frustrated man who tries to find imperfections in everyone else in order to nag at something. Turns out he wanted to be a musician and instead took the safer suit-and-tie route of life. Since Bryce’s father was never true to himself, he grew frustrated with life and hated everything free and dreamy. Unfortunately, Bryce’s main authority figure in his life was his father. In effect, Bryce learned to internalize his own emotions and stay dishonest with himself just as his father’s example showed him to. Because Bryce struggled with being honest in his emotions, it took him longer to admit to his feelings for Juli and instead of accepting it, he constantly lies throughout the story to save himself the trouble.
On the other hand, Juli was raised to value honesty and made sure to stay true to herself throughout the entire story. Her family was that of dreamers and artists who let themselves be free in their own skin, unlike Bryce’s father. She kept an open mind constantly and never failed in communicating her emotions because she was honest enough to understand them. This is why Juli was able to find the beauty in other things outside of Bryce Loski. She didn’t struggle with them, so she didn’t need to fixate on them the way Bryce did. She also understood when her feelings were lessening and never let her infatuation with Bryce blind her to his true colors.
A common theme throughout the film is that honesty is the heart of your emotions and if you are dishonest with yourself at any point in time, your emotions will become irregular, and you will get more confused. This is the main reason why it took Bryce so long to actually settle with the emotions he felt for Julie, whereas Julie knew what she wanted on the first day she met him. This movie truly paints the clear differences between being raised by open-minded parents and closed-minded parents. It also shows just how much a parent’s opinion can influence their kid’s own opinions.
Not only does the film already come with the nostalgic feeling of childhood valentines, but it also comes along with two intellectually deep perspectives for you to discuss with your partner this Valentine’s Day. This movie gives off the total vibes of staying up until midnight to make personalized Valentine’s Day cards to each of your classmates in school so no one can be left out. It’s just a sweet movie and it comes with so many different tropes and considerations that really make this the perfect movie to watch for the big day.
To Summarize
It’s no shock that the top two movies on this list are quite possibly the most versatile and inclusive movies out of the entirety of romance films. Honestly, I feel like anyone could live without watching a good majority of the films listed. However, The Princess Bride and Flipped are definitely movies that you simply cannot live without watching at least twice. So grab your popcorn and prepare to spend Valentine’s Day watching the greatest romances out there with the person you love most!
