25 Romantic Movies to Stream for Valentine’s Day

Whether single or alone, you may find yourself in need of some heartwarming fun for Valentine’s Day, here are 25 romantic movies and where they’re available to stream.

25. Chasing Amy (1997) dir. Kevin Smith

Chasing Amy tells the story of two comic book artists (Ben Affleck and Jason Lee) the former of which falls for a fellow artist (Joey Lauren Adams), but has his hopes crushed when he learns she is a lesbian. This film is very witty and tackles sexuality in an interesting way, although its 90’s politics are a bit outdated, it is still very fun to watch. It is currently streaming on HBOMAX.

24. Ghost (1990) dir. Jerry Zucker

Often labeled one of the most romantic films of all time, Ghost follows a New York City banker (Patrick Swayze), who upon being killed, begins trying to solve the mystery of his murder and protect his girlfriend (Demi Moore) from the afterlife. It’s a very sad and very heartfelt movie, and while a little bit cheesy, it’s a perfect romantic film. It’s currently streaming on Amazon Prime Video, IndieFlix, DirectTV, and Showtime.

23. Moonstruck (1987) dir. Norman Jewison

Moonstruck is less a film about romance and more a film about family, letting romance take the backseat. It follows a New York City widow (Cher) who while engaged to marry her boyfriend (Danny Aiello), falls in love with his brother (Nicolas Cage). This is the film that Cher took home an Oscar for, and has stood the test of time as a classic of the 80s. It is currently free to stream on PlutoTV and the Roku Channel.

22. Phantom Thread (2017) dir. Paul Thomas Anderson

Phantom Thread is the gothic tale of a doomed romance between a controlling dress designer (Daniel Day-Lewis) and a woman he meets at a restaurant (Vicky Krieps). This is not your typical romance and is more for the cynics out there, for it is a romance with a dark twist from a masterful filmmaker. It is currently available to stream on HBOMAX and DirectTV.

21. Sleepless in Seattle (1993) dir. Nora Ephron

Sleepless in Seattle is a melancholic romance story involving a widower (Tom Hanks) and a journalist (Meg Ryan) who hears his story of longing on a talk radio show, and begins trying to find the man. It’s a sweet story and serves as a time capsule into the time when Tom Hanks wasn’t known for his more dramatic roles and was still performing in rom-coms. It’s available to stream on DirectTV and Starz.

20. His Girl Friday (1940) dir. Howard Hawks

His Girl Friday is a classic tour-de-force in golden age filmmaking filled with intense wit and hilarious dialogue. It follows an intrepid reporter (Rosalind Russell) who returns to her old job to inform her ex-boss and ex-lover (Cary Grant) that she is getting remarried. What ensues is her boss’s increasingly asinine attempts to keep her in town and win her back over. It is currently available to stream on Amazon Prime Video, Epix, DirectTV, Classix, Kanopy, PlutoTV, Watch TCM, TubiTV, and Hoopla.

19. Jerry Maguire (1996) dir. Cameron Crowe

Most famous for it’s iconic “you complete me” line, Jerry Maguire tells the tale of, well, Jerry Maguire (Tom Cruise) a sports agent, who leaves his company to start his own with one client (Cuba Gooding Jr), and along the way falls in love with his coworker (Renee Zellweger). It’s full of heart, and chances are, it’ll give you a movie to talk about with your older family members, because they’ve definitely seen this movie.

18. Before Sunrise (1995) dir. Richard Linklater

The simplest film on this list, it follows an American man (Ethan Hawke) as he journeys off a train in Vienna with a French woman (Julie Delpy), and they journey around the sitting, being melancholic together and discussing everything about their lives. It’s a deeply personal and intimate film, following one night and one chance meeting between these two people. It’s a very well written and enjoyable film. It’s currently available to stream on DirectTV.

17. The Apartment (1960) dir. Billy Wilder

The Apartment popularized the rom-com genre, and if you’ve seen any other rom-com, you’ve probably seen the gist of this film. It follows an insurance clerk (Jack Lemmon) who lets his higher-ups use his apartments for their extramarital affairs, but he soon thinks of changing his ways when he falls for one of his coworkers (Shirley MacLaine). It has some of the most likable characters in cinema history, and makes for an excellent watch to cuddle up with a partner to. Or by yourself, it’s just as good. It’s currently streaming on Watch TCM and Hoopla.

16. Her (2013) dir. Spike Jonze

Her is a film at it’s core about loneliness. It takes place in a near future with an aesthetic both retro and modern, following a writer in the midst of a divorce (Joaquin Phoenix), who gets an AI system and begins to fall for the voice (Scarlett Johansson). It’s a very heartbreaking movie from beginning to end, and feels like a very intimate look into the lives of lonely people. While currently unavailable to stream, it can be rented through Amazon, Google Play, Redbox, Fandango Now, Apple TV, or iTunes.

15. Paterson (2016) dir. Jim Jarmusch

Jim Jarmusch is a very particular director who makes films that are about life at the center. Paterson follows a bus driver (Adam Driver) by the same name living in a town of the same name, and the day-to-day life of him and his wife (Golshifteh Farahani). It’s a very slow and patient movie that unfolds similar to a memory. It lacks a distinct plot or purpose, but rather feels like watching a few days in the life of friends or neighbors you have. I’ve never been in love, but I imagine this captures the feeling deeply. It is available to stream on Amazon Prime Video.

14. The Sound of Music (1965) dir. Robert Wise

This Best Picture winning musical is an astounding achievement. It follows a caretaker (Julie Andrews) who helps an army captain (Christopher Plummer) raise his children after the death of his wife, which of course leads to them falling deeply in love. Filled with exhilarating music and joy, the Sound of Music is timeless. It is available to stream on Disney Plus.

13. Portrait of a Lady on Fire (2019) dir. Celine Sciamma

I realized that I am over halfway through this list and I have yet to mention a queer love story. Portrait of a Lady on Fire is a slow and meditative film about a painter (Adele Haenel) who is commissioned to do a wedding portrait on a remote island of a young woman (Noemie Merlant). While I think this won’t be for everyone, if you have the patience for it, it will be rewarding experience. It is available to stream on Hulu.

12. Love, Simon (2018) dir. Greg Berlanti

Chances are, if you were a queer teen during the later 2010s, you’ve seen this film. On the off chance you haven’t, it follows a “normal” teenager (Nick Robinson) who finds an anonymous coming out post on his school’s tumblr, and begins a correspondence with the boy on the other side. It’s full of lots of heart and feels like the start to a new era of queer teen comedies. It is available to stream on Hulu, DirectTV, FuboTV, and FXNow.

11. Charade (1963) dir. Stanley Donen

While probably more famously known as “the best Hitchcock movie Hitchcock didn’t make”, Charade is full of twists and turns you’ll never see coming mixed with the classic absurdity of 60s movies. It follows a dashing woman (Audrey Hepburn) whose husband is killed under mysterious circumstances, causing her to become entangled with a handsome man she meets while on vacation (Cary Grant), and they get caught up in a plot involving espionage, murder, and theft, all while falling in love. It is available to stream on Amazon Prime Video, the Roku Channel, TubiTV, DirectTV, Kanopy, and WatchTCM.

10. La La Land (2016) dir. Damien Chazelle

I doubt this film needs any introduction, for all the Oscars it won and the acclaim it received upon it’s release, everyone and their Aunt Martha know about this movie, the tale of two struggling artists (Ryan Gosling and Emma Stone) who dance and sing their way to success in a modern day Hollywood. It is currently available to stream on DirectTV.

9. Brokeback Mountain (2005) dir. Ang Lee

The rightful winner of the 2006 Best Picture Academy Award, Brokeback Mountain follows two cowboys (Heath Ledger and Jake Gyllenhaal) who fall in love in the 1960s countryside, and the years after that as they enter and exit one another’s lives again and again. The film is heartbreaking and was a major game changer for LGBT love stories. It’s available to stream on Amazon Prime Video.

8. The Curious Case of Benjamin Button (2008) dir. David Fincher

I am strongly against the argument that this is one of David Fincher’s weakest films. The film follows Benjamin Button (Brad Pitt) who is born an old man and ages backwards his entire life. It’s an odyssey of historical events akin to Forrest Gump, and features the numerous women (Cate Blanchett and Tilda Swinton among them) who he has romances with throughout his extraordinary life. It’s available to stream on HBOMAX and DirectTV.

7. The Handmaiden (2016) dir. Park Chan-wook

I feel odd labelling this as a romance. I am not going to discuss the plot of this, because going in blind is the best choice. It’s a 1930s Korea-set tale of romance, swindling, lying, theft, and murder. It’s an elaborate film both in terms of scope and story structure, and is definitely worth your time. It’s available to stream on Amazon Prime Video.

6. Risky Business (1983) dir. Paul Brickman

Tom Cruise’s breakout hit follows a high school student (Tom Cruise) who creates a whorehouse in his basement in order to raise money to pay for a new car after an accident. It’s hilarious in the 80s way and gave us the iconic “dancing in underwear after being left home alone” scene. It’s available to stream on HBOMAX.

5. Cabaret (1972) dir. Bob Fosse

Cabaret is a dim tale of a burlesque club during 1930s Berlin as the Nazis come to power. Within the club, an MC (Joel Grey) leads an ensemble including dancer/singer Sally (Liza Minneli) as she tries to find love as their world becomes crushed by the Nazis. It’s available to stream on Hoopla and WatchTCM.

4. Singin’ in the Rain (1952) dir. Stanley Donen & Gene Kelly

One of the most iconic, if not the most iconic, movie musical of all time, Singin in the Rain follows the scramble of Hollywood to begin releasing talking pictures, prompting singers and actors including Gene Kelly, Donald O’Connor, and Debbie Reynolds to begin working on a new film. It’s sweet and heartwarming, and a classic of American film. It’s available to stream on WatchTCM and HBOMAX.

3. Starman (1984) dir. John Carpenter

While it may seem odd to see John Carpenter, king of 80s horror and sci-fi, have a movie on this list, Starman is not your typical Carpenter film. Following the death of her husband, Jenny Hayden (Karen Allen) is visited by an alien (Jeff Bridges) who takes the form of her husband. They embark on a cross country journey to get the starman to a crater where he will return to his people. It gives Jenny a chance to say goodbye to her husband, and live more of a life she lost too soon. It’s available to stream on Hulu, Amazon Prime Video, and DirectTV.

2. Some Like it Hot (1959) dir. Billy Wilder

Some Like it Hot is the outrageous tale of two Chicago-based musicians (Jack Lemmon and Tony Curtis) who witness a gang murder and disguise themselves as females in order to escape with an all-girl music troupe to Florida, where they befriend a singer (Marilyn Monroe) and try to help her find a millionaire boyfriend, all while one of them begins to fall for her, and the other attracts the attention of a very determined millionaire (Joe E. Brown). It’s outrageously funny, witty, and charming, and available to stream on Hoopla, TubiTV, and PlutoTV.

  1. When Harry Met Sally (1989) dir. Rob Reiner

One of the most acclaimed rom-coms of all time, When Harry Met Sally follows two friends (Billy Crystal and Meg Ryan) and their journey across over a decade of friendship as they try to figure out whether she should have gotten on the plane at the end of Casablanca, if women and men can be friends or not, and whether or not they are in love. Unmatched in its writing and chemistry, When Harry Met Sally is a classic of 80s cinema. It’s available to stream on HBOMAX.

If you enjoyed this article, please consider following me on Instagram @corbinwatchesmovies and on Letterboxd @CReviews03!

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store