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The 11 Most Romantic Movies to Watch on Valentine’s Day

Oh, Valentine’s Day; some love it, some hate it. Without delving too deeply into the strange, deep, and dark history of Valentine’s Day, we can still manage to find love for one another in these recent times. Whether or not you have a significant other, these movies can be enjoyed on Valentine’s Day or any other day of the year to remind us of what love can mean (at least in a Hollywood setting). Since finding gifts for each other (especially Valentine’s Day gifts for men) can be challenging, aside from the classic last-minute flower delivery, chocolates, and intimate clothing, we wanted to provide some options for indoor, at-home entertainment since most theaters, indoor restaurants, and bowling alleys will likely still be closed to admission. 

Watching Valentine’s Day movies is nothing to be ashamed of; they can bring about emotions that you never thought attainable, or they can piss you off to no end, depending on how critically you view cinema. Here today, the list of movies that we are recommending will make you think, make you laugh, and possibly make you cry (it’s okay if you’re crying alone, it’s good for you sometimes). So bust out the ice cream, chocolates, pasta, or pizza, whatever feels like a treat you deserve and enjoy this array of lovely romantic films until you can no longer stay awake or you run out of snacks. 

The Wedding Singer (1998)

One of the better Adam Sandler movies of our generation, The Wedding Singer is a genuine and sweet story of boy meets girl, and how boy wants to love girl. When a low-income wedding singer is left at the altar by what he thinks is the love of his life, he must put the pieces of his heart back together, luckily, he meets the charming Julia Sullivan (Drew Barrymore) who makes the process much easier. Full of the classic Sandler movie cameos and silly songs, this is a feel-good movie that will have your partner asking, “When are you going to do that for me?”

Director: Frank Coraci
Main Cast: Adam Sandler, Drew Barrymore, Christine Taylor
Runtime: 97 minutes
IMDb Rating: 6.8

Buy/Rent on Amazon

Shakespeare in Love (1998)

Wise and witty, Shakespeare in Love is just the right mix for your Valentine’s Day passion-quest. A young and uninspired William Shakespeare (Joseph Fiennes) is having a major writers block amidst a series of unfulfilled promises he has made, until he meets a young and rebellious Viola (Gwyneth Paltrow) who poses as a man to audition for one of his plays. Providing more than just romance, this classic ode to the Elizabethan Era maintains suspense, comedy, and utmost passion for theater and what people are willing to do to keep it alive. 

Director: John Madden
Main Cast: Gwyneth Paltrow, Joseph Fiennes, Geoffrey Rush
Runtime: 123 minutes
IMDb Rating: 7.1

Buy/Rent on Amazon

Definitely, Maybe (2008)

Definitely a chick flick, maybe one of the best, Definitely Maybe is a touching story with an all-star cast that serves up a creative slice of the rom-com genre. We explore the love life of an almost-divorced Ryan Reynolds as he explains to his daughter (Abigail Breslin) how he and her mom met, omitting the real names of his past lovers in the story for her to guess. This movie is full of sympathetic moments of intimacy and vulnerability, which all of the characters fit right into. We wouldn’t call this a typical Reynolds role, but it’s one of the best Ryan Reynolds movies for sure. 

Director: Adam Brooks
Main Cast: Ryan Reynolds, Rachel Weisz, Abigail Breslin
Runtime: 112 minutes
IMDb Rating: 7.1

Watch on Amazon

Romeo + Juliet (1996)

Another Shakespearean addition to this list, Romeo + Juliet is a masterful rendition of the age-old tale, made epically offbeat and glamorous by Baz Luhrmann. Keeping the script almost the exact same, Romeo (Leonardo DiCaprio) and Juliet (Claire Danes) meet in a modern-day (well, the 90s) Verona, where the Montagues and Capulets face-off with stylish, customized handguns to replace the elegant blades of days long gone. Complete with a contemporary, cutting soundtrack and a glorious cast, It’s a way to translate Shakespeare into a way that a younger crowd can fully understand and take to heart. 

Director: Baz Luhrmann
Main Cast: Leonardo DiCaprio, Claire Danes, John Leguizamo
Runtime: 120 minutes
IMDb Rating: 6.7

Watch on Amazon

10 Things I Hate About You (1999)

With a story based on Shakespeare’s The Taming of the Shrew and re-vamped to fit the 90s grunge of Seattle, 10 Things I Hate About You is a timeless classic, giving high-school rom-coms a run for their money. In an upper-middle-class Seattle high school, Bianca (Larisa Oleynik) is a popular and beautiful girl that many would feel lucky to date (arrogant schmucks and romantic nerds alike), but with her terrified and controlling father, she is not allowed to date unless her blunt and abrasive older sister, Kat (Julia Stiles) decides to date somebody. Starring a wide array of recognizable faces and witty dialogue, at least one of you will fall victim to Heath Ledger’s endlessly charming smile. 

Director: Gil Junger
Main Cast: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt
Runtime: 97 minutes
IMDb Rating: 7.3

Watch on Disney+

Always Be My Maybe (2019)

If you’re looking for a good romantic comedy on Netflix, Always Be My Maybe is a great place to start. The story follows Sasha (Ali Wong) and Marcus (Randall Park), two people who everyone assumed would end up together. After reconnecting after 15 years apart, they begin to think maybe they are meant to be.

Director: Nahnatchka Khan
Main Cast: Ali Wong, Randall Park, James Saito
Runtime: 101 minutes
IMDb Rating: 6.8

Watch on Netflix

Moulin Rouge (2001)

In the second Baz Luhrmann title on our list today, Moulin Rouge is a glorious spectacle of musical talent and romantic tragedy. A penniless poet (Ewan McGregor) begins to fall in love with a lovely, sultry, courtesan singer (Nicole Kidman), whose hand has been promised to a duke in order to fund the next big production for the Moulin Rouge. With surprising musical performances from McGregor as well as Kidman and visceral scenes of emotional distress highlighted by extreme color schemes, this musical is unlike any you will see. 

Director: Baz Luhrmann
Main Cast: Nicole Kidman, Ewan McGregor, John Leguizamo
Runtime: 127 minutes
IMDb Rating: 7.6

Buy/Rent on Amazon

The Big Sick (2017)

The Big Sick is based on the real-life love story of comedian Kumail Nanjiani and Emily V. Gordon. The story follows Nanjiani as he struggles to build up a career in stand-up. After a run-in with a heckler named Emily (Zoe Kazan), a relationship quickly forms. However, the couple is faced with a family pushback and when they break up, a coma is what brings them back together. This original dramedy is one of the best Prime movies Amazon has to offer.

Director: Michael Showalter
Main Cast: Kumail Nanjiani, Zoe Kazan, Holly Hunter
Runtime: 120 minutes
IMDb Rating: 7.5

50 First Dates (2004)

Another Adam Sandler rom-com, also featuring Drew Barrymore, 50 First Dates is a comical dramedy that honestly gets pretty sad but has some moments of wonderful devotion and love to aspire to (even though it’s just a movie). Henry Roth is portrayed as a ladies man who can’t commit, which, in all honesty, falls by the wayside pretty quickly in the plot, but when he finally meets the girl of his dreams, she turns out to have short-term memory loss, resetting the clock every day when she goes to sleep. Besides being a bit corny and a little lazy in its writing, the moments of love and adoration are something to behold, especially if shared with your loved one and the tears can be contagious. 

Director: Peter Segal
Main Cast: Adam Sandler, Drew Barrymore, Rob Schneider
Runtime: 99 minutes
IMDb Rating: 6.8

Watch on Netflix

Lost in Translation (2003)

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Beautifully executed and seamlessly transitioning between comedy and romance, Lost in Translation is a critically acclaimed masterpiece of epic proportions. When a sad, lonely movie star (Bill Murray) serendipitously meets a newly married and skeptical young woman (Scarlett Johansson) in Tokyo, the chemistry is instant and their facades quickly fade. Fans of Murray’s work will undoubtedly enjoy this Sofia Coppola classic.

Director: Sofia Coppola
Main Cast: Bill Murray, Scarlett Johansson, Giovanni Ribisi
Runtime: 102 minutes
IMDb Rating: 7.7

Watch on Amazon

Eternal Sunshine of the Spotless Mind (2004)

In a conceptual tour de force film, Eternal Sunshine of the Spotless Mind is a cinematic masterpiece in which genre, narrative, and the very concept of memory is challenged. Joel (Jim Carrey) is on a train for his usual commute when he meets Clementine (Kate Winslet), a quirky, overtly forward individual, who makes outrageous statements that catch our protagonist’s ear. When their relationship gets nasty, they individually seek out the help of an experimental memory-removal clinic that reminds them exactly why they belong together. This is a fantastic love story and arguably one of the best Jim Carrey movies ever. 

Director: Michel Gondry
Main Cast: Jim Carrey, Kate Winslet, Tom Wilkinson
Runtime: 108 minutes
IMDb Rating: 8.3

Buy/Rent on Amazon

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