20 of the Most Highly Rewatchable Romance Movies

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Sometimes, all you need is a night in which you watch your favorite romance movies. It can be one you’ve seen a hundred times, but it’s still special all the same. A period piece, a romantic comedy, or even a movie that focuses on a break-up that disguises itself as a romance could be what you’re in the mood for.

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Romance movies are so special because they can take on so many different identities that you genuinely have hundreds to choose from. The ones you’ve seen more than ten times and can easily recite lines from hold a higher ranking than most and deserve some recognition. Here’s a list of twenty of the most highly rewatchable romance movies.

Update February 9, 2024: Valentine’s Day is fast approaching, so this article has been updated with even more romances that are just so rewatchable and where you can stream every title if you want to rewatch them again.

20 Pretty Woman (1990)

Pretty Woman is a 1990 film starring Richard Gere and Julia Roberts that took the world by storm. A modern take on the fairytale love story, the movie tells the story of a wealthy business tycoon, Edward Lewis (Gere), who hires a Hollywood escort, Vivian Ward (Roberts), to accompany him to his business gatherings. But along the way, the two of them fall in love and things start to become more complicated than any of them initially signed up for.

Why It’s Rewatchable

The movie’s most delightful charm is the hope it fills your heart with. It talks about how love finds its way to you even in the most hopeless circumstances. The movie was initially not planned as a romcom, but we are glad it was as it became one of the pioneers of the genre. Julia Roberts was also catapulted into stardom due to her phenomenal performance beside Gere in the film, and her acting in the film is still as delightful to watch as it was in 1990. Stream on Hulu

19 The Holiday (2006)

Nancy Meyers movies have a way of creeping into your heart and making a home there, and The Holiday is no different. The film tells the story of a successful American woman named Amanda (Cameron Diaz) who decides to swap homes with a lovelorn English woman named Iris (Kate Winslet) for the holidays. Amanda falls in love with Iris’s brother Graham (Jude Law), while Iris finds her purpose out of her failed relationship in helping people and building a close relationship with Amanda’s associate Miles Dumont (Jack Black).

Why It’s Rewatchable

As the name of the film suggests, it is filled to the brim with holiday spirit and the magic of love. But it’s more than that. The movie is about two women, completely different in their personalities, learning to take a step outside their comfort zones to achieve the things they want in their life. The movie portrays change and all the beauty that comes with it really well. And at the end of the day, the lighthearted love story becomes a really rewatchable classic holiday movie. Stream on Netflix, Starz, and DirecTV

18 He’s Just Not That Into You (2009)

He’s Just Not That Into You features an all-star cast that includes Ginnifer Goodwin, Justin Long, Bradley Cooper, Scarlett Johansson, Drew Barrymore, Jennifer Connelly, Jennifer Aniston, and Ben Affleck. The movie follows nine people and their varying romantic problems as the various characters interact with each other’s story. The movie is a modern-day romance that serves as an interesting examination of how dating has evolved in the 21st century through texting and social media, and now it is more interesting to see how much has changed since.

Why It’s So Rewatchable

With a wide array of storylines and intersecting characters, there really is something for everyone in He’s Just Not That Into You, from a young woman struggling to find a romantic connection and making one with a smooth-talking bartender to a man having an affair with a younger woman and his wife learning about it and going out on her own, to a couple at a crossroads in their life on if they want to get married. He’s Just Not That Into You is a great comfort watch as it has a nice balance of happy endings and fitting breakups. The movie is also an interesting snapshot of many people’s careers in 2009. Rent or Purchase on AppleTV+, Vudu, and Prime Video.

17 Chungking Express (1994)

Ocean Shores Video

Chungking Express is a genre blend of romance, crime, drama, and occasional comedy that can only come from a masterful filmmaker such as Wong Kar-Wai. The movie, set in two different timelines, tells the story of two cops, both getting over their breakups and finding romance amidst their busy schedules and heartbreaks. With amazing performances from the main cast, the movie leaves a lingering sense of heartache even after you finish watching.

Why It’s Rewatchable

Wong Kar-Wai is the master of artfully twisting heartbreak and romance together to weave a stunning tale that leaves you breathless. Even as an anthology, the two stories of the movie feel like they are a part of each other even when they are distinct in their beauty. The film is undoubtedly one of Wong Kar-Wai’s best works, and you will find yourself watching it at different points of your life and coming up with new things to love about it every time. Stream on Max

Related: 10 Iconic Cheerful Meets Grumpy Romances in Movies

16 Someone Great (2019)

Someone Great
Netflix

You might be surprised when you see this movie on the list full of great romance flicks, but honestly, if you need a good cry after going through a breakup with your beloved, pop this one in. Someone Great captures a relationship that was once so beautiful and sacred that when they broke up, it was devastating. Jenna and Nate were good until they weren’t, and their breakup was so well done that by the time the movie is over, you’ll be feeling like you went through something of the same caliber.

Why It’s Rewatchable

Someone Great is less of a romance movie and more of a movie about moving on with the help of your friends who love you no matter what. This movie pairs its sad scenes with some great comedic relief, strong friendships, and the act of finding yourself after a painful breakup. Albeit devastating, it offers solace to the heartbroken and helps them heal on their own accord. Stream on Netflix

15 Red, White & Royal Blue (2023)

Red White and Royal Blue
Amazon Prime Videos

Based on Casey McQuiston’s novel of the same name, Red, White & Royal Blue is a sweet romance story between the son of the president of the USA, Alex Claremont-Diaz (Taylor Zakhar Perez), and British Prince Henry (Nicholas Galitzine). Their secret enemies-to-lovers affair is the main focus of their story as it gets them into a lot of hilarious trouble and ultimately poses Henry with the ages-old question – will he choose his love or his duty?

Why It’s Rewatchable

The book the movie was based on was a globally beloved romantic novel, and it was translated to screen near-perfectly with stellar performances from both the main actors and the supporting cast. The movie is an elaborate tale that might never actually happen, but the sweet and happy ending makes us hopeful for a better world where love of all kinds is accepted with open arms. It is no doubt one of the most adorable queer romcoms of our time, and you can watch the movie multiple times and fall in love with Alex and Henry each time. Stream on Prime Videos

14 10 Things I Hate About You (1999)

Under Gil Junger’s careful and introspective direction, this modern take on a classic Shakespeare play, The Taming of the Shrew, took the ‘90s by storm and ended the decade with a classic that went on to become one of the most rewatchable romance movies ever made. Set in 90s Seattle, 10 Things I Hate About You follows Cameron, a new guy in school trying to win the affection of Bianca, the most popular girl. Turns out Bianca cannot date unless her rebellious and headstrong older sister Kat also has a boyfriend. So, Cameron asks bad boy Patrick to change Kat’s mind and take her to the school dance.

Why It’s Rewatchable

Julia Stiles as Kat and Heath Ledger as Patrick share irresistible chemistry as they navigate first love and fight the urge to drop everything and embrace. The youthful humor, classic 90s fashion, and a killer soundtrack all elevate the film. As one of the pioneering romcoms of the 90s, the film has perfectly retained its charm with a compelling storyline and nostalgia. 10 Things I Hate About You still remains one of the most rewatchable movies even after 25 years of its release. Stream on Disney+

13 Moonstruck (1987)

Moonstruck
Moonstruck

Release Date
December 16, 1987

Director
Norman Jewison

Sometimes a romance movie can be very complex and have many twists and turns, and sometimes it’s a movie about a very traditional Italian family that’s a bit messy when it comes to love. Moonstruck is everything you want and need in a movie like this; it’s comforting, it’s warm, and Cher and Nicolas Cage are a duo you won’t expect but will appreciate by the time it’s over.

Why It’s Rewatchable

The story of how their characters fall in love is unconventional since it involves infidelity, but you’ll forget all about Johnny as you watch the real love story unfold before you. Moonstruck is so rewatchable because of how familiar it is and how it won’t leave you feeling unsatisfied by the end of it. Also there is the obvious fact of having two charismatic movie stars like Cher and Nicolas Cage that make this a pleasure to revisit. Buy or Rent on AppleTV+, Vudu, or Prime Video

12 Dirty Dancing (1987)

dirty dancing
Dirty Dancing

Release Date
August 21, 1987

Director
Emile Ardolino

When you watched Dirty Dancing for the first time, did you wish you could have a steamy summer fling at a campground with a hunky instructor? You’re certainly not alone if the answer is yes. Dirty Dancing is one of those movies that makes you long for summer and wish that Patrick Swayze would teach you how to ballroom dance, even if he’s a bit grumpy.

Why It’s Rewatchable

One can’t deny the influence this movie has had on pop culture; if you hear the first few beats of “I’ve Had the Time of My Life,” you immediately think of the iconic lift scene. Dirty Dancing is also so easy to watch and a great time capsule of the 1980s that still is as moving and powerful as it was when it first hit theaters. Stream on Hulu

11 (500) Days of Summer (2009)

(500) Days of Summer might not be a traditional romance; after all, the movie tells you it’s a story about love, but it is not a love story. Yet it is hard to argue that when it comes to modern 21st century romances, (500) Days of Summer has become a modern classic. The film went from an indie Sundance darling to a mainstream hit, thanks in no small part to the wonderful chemistry between lead stars Joseph Gordon-Levitt and Zooey Deschanel.

Why It’s Rewatchable

The non-linear narrative of (500) Days of Summer makes for a fun game every time one watches it to track the progression of the relationship and catch key points. Yet it is the fact that the movie doesn’t have a traditional romantic ending that has made it so enduring for years. The movie starts with a breakup and recounts a relationship, so there is reliability that audiences have with it since everyone can relate to the feeling of a messy breakup and eventually finding the emotional catharsis of moving on. The movie has a warm glow that is fun to revisit and is a reminder of a time when small indie rom-coms could break out at the box office instead of being sent straight to streaming, where they are sadly often forgotten about. Stream on Hulu.

Related: Best Movies to Watch When You’re Single in February

10 When Harry Met Sally… (1989)

Trying to answer the universal question of whether a man and a woman can ever just be friends When Harry Met Sally… is Rob Reiner’s darling film from the 80s. Billy Crystal and Meg Ryan debate the question subtly and playfully across 12 years in this legendary romance. From their first chance meeting to the Ulysses desk scene, we witness Harry and Sally’s friendship, attraction, romance, and the way their eyes dance between picking one of the three. They spar with the chemistry and understanding of an old married couple. Yet, when faced with the idea of dating, they take a step back.

Why It’s Rewatchable

Other than the fantastic main actors, the film also has an outstanding supporting cast, with Bruno Kirby and Carrie Fisher making cameos. The movie outlines a lot of modern dating problems and trust issues that a lot of people still suffer from. But as Harry and Sally finally get married after 12 years of knowing and growing to love each other, the movie shines us with a glimmer of hope. Thus, even after 30 years, revisiting the movie is as comforting and reassuring as ever. Rent or Purchase on Apple TV+, Prime Video, and Vudu.

9 Bridget Jones’s Diary (2001)

Renée Zellweger shines so brightly in this iconic film adapted from Helen Fielding’s 1996 novel. Bridget Jones’s Diary follows Zellweger casually tracking her year by keeping a journal and hoping that by the end of it, she has a clear path of changing her life. Between smoking and unfortunate run-ins, she navigates the dating scene as well as her career. But the arrival of two suitors brings a drastic improvement in her beliefs. Played by Hugh Grant and Colin Firth, these men bring perspective and charm to a single woman’s life.

Why It’s Rewatchable

Sharp jokes and heartwarming moments make Bridget Jones’s story more immersive. Beyond the movie, Bridget is a character whose antics always lift your spirits and cheer you on. It is one of the best rom-com movies to have come out of the 00s and has remained one of the most charming films about a working woman finding her Mr. Right with an unlikely person. It also launched a very nice trilogy of films with 2004’s Bridget Jones: The Edge of Reason and 2016’s Bridget Jones Baby. Stream on Paramount+

8 La La Land (2016)

La La Land is a vibrant ode to chasing Hollywood dreams in 1950s Los Angeles. Emma Stone’s Mia is a coffee shop employee who desperately wants to become an actress, and Ryan Gosling’s Sebastian is a pianist who wants to make it big as a professional. Crossing paths and falling in love was never the plan, but what could be more joyous than letting your heart win? Their lush musical duets whisk us away into a simpler time when the passions of youth were greater than the sorrows of life.

Why It’s Rewatchable

Although the ending is bittersweet, the movie is beautiful. It leaves hope that somewhere, two dreamers might find each other again. The movie paints love in a more realistic way than most romance films and teaches the lesson that not all love stories have a satisfying ending. With its brilliant soundtrack and the amazing chemistry between Gosling and Stone, the film can be watched time and time again. Overall, the colorful aesthetic and nostalgia work as important factors in making La La Land a dreamy escape. Rent or buy on Apple TV and DirecTV

7 Before Sunrise (1995)

The movie that gave us something to add another item to our bucket list, Before Sunrise centers around Jesse, an American man, and Celine, a French woman, who meet on a train to Europe. Feeling an instant connection with the woman sitting across from her, Jesse cannot help but ask Celine to spend an evening with him, traversing 1990s Vienna before he returns to the US. Ethan Hawke and Julie Delpy bring raw charm and quiet reflection to the story as two people on the wings of new love.

Why It’s Rewatchable

Director Richard Linklater is known for his minimalist style, which lets both the character’s intellect and playful banter carry the entire weight of storytelling. Although fleeting, Jesse and Celine’s relationship teaches you to truly listen, understand, and appreciate one another. The movie is the first part of a trilogy, with the other two films being Before Sunset and Before Midnight. The three movies all tell the story of the same couple and are perfect for a binge-watching weekend. Rent or buy on Apple TV

Related: 10 Best Romantic Comedies Directed by Women You Shouldn’t Skip

6 To All The Boys I’ve Loved Before (2018)

Noah Centineo as Peter and Lana Condor as Lara Jean in To All the Boys I've Loved Before (2018).
Netflix

Starring Noah Centineo and Lana Condor, To All The Boys I’ve Loved Before became one of the best romcoms of the last decade when it came out in 2018. The film tells the story of Lara Jean (Condor), who wrote letters to all her crushes when she was a kid but never sent them. When her sister sends the letters to their intended recipients, one of her old crushes, Peter (Centineo), asks her to fake date him to make his ex jealous. But when fake dating turns into real feelings, Peter and Lara-Jean find themselves in uncharted territory.

Why It’s Rewatchable

It’s a teen romance story with one of the cutest on-screen couples of the last few years, so it is not hard to fall in love with the film. The film, which was based on a book, went on to have two more spin-offs, both of which were just as full of heart and love as the first one. Now Netflix has also released a spinoff series about Lara-Jean’s sister Kitty (Anna Cathcart) and her own love story. The films are comforting and charming with their bright color palettes and sweet dialogue that will put a smile on your face every time you watch it. Stream on Netflix

5 Notting Hill (1999)

Notting Hill stars Julia Roberts and Hugh Grant in a sweet romance between a London bookshop owner and a famous Hollywood actress. Hugh Grant plays the role of a divorced bookstore owner, William Thacker, whose fated run-in with actress Anna Scott results in a whirlwind romance filled with heartfelt conversations and the paparazzi looking for a scandal.

Why It’s Rewatchable

Both Hugh Grant and Julia Roberts were the darlings of the 90s romcoms, and it is a treat to watch them bring life to the screen when they are together. The movie tells a familiar tale of a famous woman falling in love with a common man, which changes both of their lives. But the movie is adorable in its simplicity, and its hilarious moments from the supporting cast of characters to the genuine heartfelt big grand romantic ending make this movie a great one to revisit time and time again. Stream on Amazon Prime Video

4 Pride and Prejudice (2005)

Keira Knightley as Elizabeth and Matthew Macfadyen as Mr. Darcy in Pride & Prejudice
Focus Features 

Pride and Prejudice (2005) is quite possibly the best period romance movie to date. It’s certainly one of the better adaptations of Jane Austen’s work because of how well they translate the words to the screen through emotion and action. If you are familiar with the story of Elizabeth Bennet and Mr. Darcy, then this is a film you absolutely have to watch as it will make you fall in love with the classic even more deeply.

Why It’s Rewatchable

Matthew Macfadyen was a wonderful choice for Mr. Darcy because of how much angst he portrayed, and Keira Knightley as Elizabeth Bennet is truly a knockout. Maybe this movie makes the top of your list because of the iconic hand flex scene, and if you know, you know. Do we even mention the rain-soaked proposal scene? Yes, we’re swooning. And if you are a fan of period romances where much is said without saying anything at all, you will find yourself visiting the film again and again whenever you feel down. Stream on Peacock

3 Crazy Rich Asians (2018)

Crazy Rich Asians gets a lot of things right when it comes to a great romance movie because of how it truly takes you on a journey throughout the majority of the film. Rachel and Nick’s romance is very sweet until you realize how evil and intense Nick’s mother is and the extremes she goes to to break them up.

Why It’s Great

Crazy Rich Asians will make you laugh, cry, swoon, and wish you were part of this luxurious and rich family. Even with a romance story at the center, the movie manages to highlight strong women through Rachel and Nick’s sister, Astrid, who does not look back while leaving her cheating husband. The wedding scene alone will have you rewatching, but if you find love stories with different tax brackets and meddling mothers, you’ll find yourself adding this to your list of favorites. We are still waiting on that sequel and until it comes, we will continue to enjoy the first film. Stream on Hulu

2 The Princess Bride (1987)

The Princess Bride is a really special romance film that might make you feel nostalgic while watching it. If you grew up in the late ’80s and early ’90s, chances are, you watched this movie or have at least heard of it. If anything, you must have heard someone recite the iconic line, “Marriage… marriage… marriage.”Or, “My name is Inigo Montoya. You killed my father. Prepare to die.”

Why It’s Rewatchable

The love story between Westley and The Princess Bride will take you on a full-fledged adventure filled with action, lighthearted humor, and the perfect amount of romance. The film is a great fit for people of any age, and it is something from your childhood that you can share with your children, and they will love it just as much as you did. It’s rewatchable not only for the quotes but also for the amount of heart it displays. Stream on Disney+

1 Casablanca (1942)

Casablanca
Casablanca

Release Date
November 26, 1942

Director
Michael Curtiz

In the wise words of Lorelai Gilmore, “Casablanca? You’ve never seen Casablanca? What is wrong with you?” Casablanca is one of those movies that stands the test of time within the romance genre. It was filmed during World War II, so you can imagine tensions were high, with the plot revolving around a man who helps his ex-lover and her husband hide from Nazis.

Why It’s Rewatchable

Ingrid Bergman and Humphrey Bogart make the movie one of the greatest love stories of all time. The black-and-white setting is smoky and intimate, and it’s such an easy watch simply because it’s Casablanca. You know exactly what you’re going to get, and yet it’s an absolute delight every time you press play. The movie is 82 years old, but it still feels just as fresh, captivating, and lovely as it must have been when it was first released. This is a cinematic romance audiences have returned to time and time again and that won’t stop anytime soon. Stream on Max

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