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With Valentine’s Day 2025 around the corner, it's that time of the year again when cinephiles can selfishly indulge in sappy romantic movies that make them cry happy tears. While it is true that romantic comedies have been around for a long time with new titles released every year, there is something very special about classic rom-coms that are still remembered for their heartwarming storytelling.
This Valentine’s Day 2025, movie lovers should make a point to indulge in classic romance gems instead of settling on the first clichéd rom-com that pops up on their favorite streaming platform. However, it won't be easy to know which title to pick for Valentine’s Day 2025, amidst the ever-growing collections across multiple platforms.
This list containing 10 must-watch classic rom-coms will act as a guide for romantics who want to find deserving options to stream on Valentine’s Day 2025.
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Disclaimer: This list contains information from various sources.
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1) Roman Holiday (1953)
This classic movie starring Audrey Hepburn and Gregory Peck is a great option for Valentine’s Day 2025. Directed by William Wyler, it focuses on Hepburn's Crown Princess Ann who is on a tour of European capital cities.
Tired of always having to stick to a tight schedule, she sneaks out of the embassy. She then goes exploring with Peck's Joe Bradley, an American reporter, who she meets by coincidence.
The chemistry between Hepburn and Peck is one of the biggest reasons to stream this classic rom-com on Valentine’s Day 2025. There is something genuine and relatable about their interactions that captures the thrill of a budding romance.
The fact that not all is captured in dialogue but also through subtle body language and expressive facial expressions also adds to the viewing experience. It is also endearing to see Ann grow as a person after experiencing all the things that she had always wanted to do but couldn't because of her royal status.
Where to watch: This Valentine’s Day 2025, stream Roman Holiday on Apple TV+ and Prime Video.
2) Breakfast at Tiffany's (1961)
The fact that this is the second title on this list starring Audrey Hepburn makes it clear that no Valentine’s Day 2025 watchlist would be complete without a touch of that classic Hepburn charm. This classic romantic comedy by Blake Edwards is inspired by Truman Capote's 1958 novella.
Hepburn plays Holly Golightly, a quirky socialite who isn't the easiest to get along with. When George Peppard's Paul Varjak, moves into her building, he finds himself drawn to her from the get-go. Over time, they start to bond, but their relationship isn't without its challenges because both of them have very different opinions about love and commitment.
The opening scene wherein Holly eats breakfast outside a Tiffany's store window while admiring the jewelry is so iconic that even viewers who haven't watched the movie have seen it. Hepburn played many iconic roles throughout her career and this is one of them. From the immaculate costumes to her charismatic personality, Holly is a character who leaves a lasting impression.
Where to watch: Watch Breakfast at Tiffany's this Valentine’s Day 2025 on Prime Video and Apple TV+.
3) Some Kind of Wonderful (1987)
Cinephiles who adore thoughtful coming-of-age narratives should add this movie by Howard Deutch to their Valentine’s Day 2025 watchlist. Eric Stoltz plays Keith Nelson, a blue-collar teen who has always dreamed of going out with Lea Thompson's Amanda Jones. When he is finally able to muster up the courage to ask her on a date, things seem to be looking up.
However, several complications arise that threaten their relationship. Eric's best friend Watts (Mary Stuart Masterson) realizes that she has feelings for him and at the same time, Amanda's ex-boyfriend starts to plot his revenge.
Some Kind of Wonderful thrives on a feel-good narrative that features angsty young characters who are trying to figure out their place in the world. This Valentine's Day 2025, stream this classic movie to learn valuable lessons about long-lasting friendship and sincere love.
Where to watch: This Valentine’s Day 2025, stream Some Kind of Wonderful on Apple TV+ and Prime Video.
4) Say Anything... (1989)
Romantics who are planning a movie marathon on Valentine's Day 2025 shouldn't forget to add this heartfelt movie starring John Cusack and Ione Skye to the list. Cameron Crowe's feature directorial debut captures the butterflies of new love along with all the anxiety and uncertainty of becoming an adult.
Cusack plays Lloyd Dobler, a good-hearted underachiever who is head over heels in love with Skye's Diane Court. As Diane is the valedictorian, her classmates, and family have a hard time understanding why she is attracted to Lloyd. When her father encourages her to cut him off before she leaves for college, they realize that they actually need one another more than they realized.
The chemistry between the leads and the lessons the movie shares about the complexities of adult relationships make it a great addition to any Valentine’s Day 2025 movie night. It is also endearing to see the bond between Diane and her father. Even though it's not perfect, they are willing to put in the effort to really listen and understand each other.
Where to watch: Watch Say Anything... this Valentine’s Day 2025 on Disney+, Hulu, Apple TV+ and Prime Video.
5) Defending Your Life (1991)
For Valentine's Day 2025 watchlists that need a little pizzazz, this Albert Brooks movie is the perfect addition. Brooks doesn't only work his magic behind the camera but also stars as the lead protagonist. He plays Daniel Miller, an advertising executive from Los Angeles who meets with an unfortunate accident and is transported to the afterlife.
The afterlife doesn't look anything like he had imagined before and he realizes that he has to go through proceedings that entail examining his lifelong fears. The outcome of which will determine whether he'll be reincarnated again on Earth, or move on to the next phase of existence. As if it wasn't complicated enough, falling in love with Meryl Streep's Julia adds to his quandary.
It is a treat to see the protagonist fall in love but it's also endearing to see him better understand the meaning of life and death during his time in the afterlife. The meaningful lessons put forward by the well-written narrative of this movie will surely sweeten every viewer's Valentine's Day 2025 celebration.
Where to watch: This Valentine’s Day 2025, stream Defending Your Life on Prime Video and Apple TV+.
6) Sleepless in Seattle (1993)
Valentine's Day 2025 will certainly feel incomplete without binging on this classic movie by Nora Ephron which continues to be one of the most successful romantic comedies in box-office history.
Tom Hanks plays Sam Baldwin, a recently widowed architect who moves to Seattle with his son Jonah (Ross Malinger). When Jonah tricks Sam into sharing about his deceased wife on air during a radio talk show, his words strike a chord with Annie Reed, a Baltimore Sun reporter portrayed by Meg Ryan. Even though they have never met, Annie can't help but feel that Sam might be "the one".
Romantics who want reaffirmation about love and destiny this Valentine's Day 2025 will find themselves immersed in the simple but sincere screenplay of Sleepless in Seattle. The characters are relatable and the dialogue perfectly switches between witty and emotional, depending on the scene.
Where to watch: Watch Sleepless in Seattle this Valentine’s Day 2025 on Netflix, Apple TV+ and Prime Video.
7) Clueless (1995)
Fans of Paul Rudd won't regret adding this Amy Heckerling rom-com to their Valentine’s Day 2025 watchlist as it marks the actor's film debut. It stars Alicia Silverstone in lead who plays Cher Horowitz. She is a good-natured teenager deep down but often acts spoiled because she comes from a wealthy family.
Cher loves to find "projects" that she can keep busy with, and her latest victim is the shy new student Tai Frasier, portrayed by Brittany Murphy. While she helps give Tai the ultimate makeover which makes her popularity skyrocket, Cher also has to deal with Rudd's Josh Lucas. He is the level-headed son of her father's ex-wife who he was married to only briefly.
There is no doubt that the real star of this movie is Silverstone. She beautifully captures Cher's growth as a person as she realizes that there is much more to a person than outward appearances. This Valentine's Day 2025, revel in the witty banter between Cher and Josh that hints at a deeper connection that even they don't realize at first.
Where to watch: This Valentine’s Day 2025, stream Clueless on Apple TV+, Prime Video and Roku.
8) My Best Friend's Wedding (1997)
This classic movie by P. J. Hogan deserves to be on every Valentine’s Day 2025 watchlist because it offers the perfect blend of romance and comedy. Julia Roberts plays food critic Julianne Potter also known as Jules. She has been best friends with Dermot Mulroney's Michael O'Neal for a long time.
Jules believes that the romance is in the offing but the dream crashes when Michael announces he is getting married to Cameron Diaz's Kimmy. Jules then decides to sabotage the wedding and make him fall in love with her.
This movie is perfect for Valentine’s Day 2025 because of its light-hearted and humorous storyline. Even though Jules isn't the most virtuous protagonist, she has plenty of redeeming qualities that will make the audience fall in love with her. Both Roberts and Diaz have excellent comedic timing which adds to the viewing experience.
Where to watch: Watch My Best Friend's Wedding this Valentine’s Day 2025 on Netflix, Disney+, Apple TV+ and Prime Video.
9) You've Got Mail (1998)
This is the second Nora Ephron title on this list of movies to stream for Valentine’s Day 2025 which is hardly surprising given the filmmaker's ability to tell relatable stories. The beloved duo of Tom Hanks and Meg Ryan are back but in this movie, they play Joe Fox and Kathleen Kelly respectively.
Joe is part of Fox Books, a family that runs a major chain of bookstores. Kathleen runs an independent children's bookstore which she inherited from her mother. She hates Fox Books because the major chain is running small bookstores like hers out of business. Unknowingly she befriends a stranger online who just so happens to be Joe.
Ephron's attention to detail really shines through in this popular rom-com perfect for Valentine's Day 2025. It also helps that Hanks and Ryan have impeccable chemistry together which prompts the audience to root for them. Movie lovers won't regret adding this to their Valentine’s Day 2025 watchlist because the endearing plot will bring a smile to their lips.
Where to watch: This Valentine’s Day 2025, stream You've Got Mail on Hulu, Prime Video and Apple TV+.
10) 10 Things I Hate About You (1999)
What makes this movie by Gil Junger a perfect choice for Valentine’s Day 2025 is its relatable narrative that stays relevant to this day. 10 Things I Hate About You stars Heath Ledger, Julia Stiles, Larisa Oleynik, Joseph Gordon-Levitt, and more. It is a modern retelling of William Shakespeare's The Taming of the Shrew.
Gordon-Levitt's Cameron wants to date Oleynik's Bianca but her father has a strict dating policy. In order to make things easier for them, Cameron convinces Ledger's Patrick to get into the good books of Bianca's elder sister, Kat (Stiles).
Cinephiles who want to find a meaningful romantic movie to watch this Valentine’s Day 2025 should look no further. 10 Things I Hate About You thrives on an intelligent screenplay elevated by well-developed characters and poignant messages about staying true to oneself.
Where to watch: Watch 10 Things I Hate About You this Valentine’s Day 2025 on Prime Video and Disney+.
This Valentine’s Day 2025, movie lovers should make a point to indulge in these classic rom-coms that will leave a lasting impact with their moving storylines and lovable characters.
