The Top 31 Best Movies To Watch This Valentine’s Day
Valentine’s Day is once again upon us. While many will take their partner out for a fancy dinner or fun activity, another great option is to host a movie night. Nothing says “I love you” more than ordering UberEats and snuggling up on the couch with a film. The latest action flick or superhero movie probably won’t cut the mustard, so we’ve selected a bunch of great movies that tie in with Valentine’s Day. From romcoms and soppy dramas to heartbreaking tearjerkers and inspirational love stories, there’s something here for everyone with our list of the best Valentine’s Day movies.
So pop open a bottle of wine, grab some popcorn, get comfortable, and settle in for a romantic movie marathon with these great Valentine’s Day movies.
1. Crazy Rich Asians
One of the biggest films of 2018 is also one of the funniest. Crazy Rich Asians follows Rachel Chu as she heads to Singapore to meet her boyfriend’s super-rich parents. It’s a fish out of water tale with plenty of laughs and a great support cast that includes Awkwafina, Jimmy O. Yang, Michelle Yeoh, and Ken Jeong.
Possibly an unusual choice, but we are so connected to our phones these days it makes sense to feature a movie about a man who falls in love with his phone’s operating system. Joaquin Pheonix’s Theodore is a lonely letter writer who becomes enamored with his phone’s AI Samantha, voiced by Scarlett Johansson. It’s a fantastic meditation of love, technology, and relationships in the modern era.
3. Love Actually
While many believe this movie to be a Christmas classic, it’s also relevant when Valentine’s Day comes around. Love Actually revolves around 10 stories about love featuring an ensemble cast including the likes of Hugh Grant, Keira Knightley, Liam Neeson, Emma Thompson, Colin Firth, and Billy Bob Thornton. It will make you laugh, it will make you cry, and it will keep your girlfriend happy.
4. Romeo + Juliet
I’m not a fan of Baz Luhrmann, but even I have to admit his take on Shakespeare’s Romeo and Juliet is incredible. The famous tale is given a technicolor overhaul, with Luhrmann’s trademark visuals and pop culture influences giving the film a wonderful edge. Leonardo DiCaprio and Clare Danes are magic as the two leads, with able support from Brian Dennehy, John Leguizamo, Pete Postlewaite, and Paul Sorvino.
5. Eternal Sunshine of the Spotless Mind
Written by Charlie Kaufman and directed by Micheal Gondry, this film is akin to a visual acid trip. Eternal Sunshine of the Spotless Mind follows Jim Carrey and Kate Winslet, former lovers who have their memories of each other erased from their minds. It’s a confronting and involving look at relationships gone bad and whether forgetting the past makes for a better future.
6. When Harry Met Sally
Forever known as the film with the cafe orgasm scene, there’s much more to When Harry Met Sally. The movie is an intriguing look at how two people grow as their relationship develops over 12 years of chance encounters and planned dates. This is prime Billy Crystal, with the film somewhat of a breakout feature for Meg Ryan.
7. Always Be My Maybe
Ali Wong continues to demonstrate why she is one of the best comedians going around with Always Be My Maybe. Wong co-wrote the Netflix comedy with fellow actor Randall Park and screenwriter Micheal Golamco. Wong and Park play former friends who reconnect years after a failed date and find they still have feelings for each other. Hilarious, heartbreaking, and poignant, Always Be My Maybe is a fantastic date film. It also features one of Keanu Reeves’ greatest performances.
8. The Notebook
No list of romance films to watch on Valentine’s Day would be complete without The Notebook. A classic romantic drama starring a fresh-faced Ryan Gosling and Rachel McAdams, The Notebook is a real tearjerker, especially the ending. Although it didn’t rate well with the critics, the film was a box office hit and helped propel Gosling into the mainstream.
9. Valentine’s Day
As the title suggests, this film takes place on Valentine’s Day. The movie follows a group of people living in Los Angeles whose lives intersect on the yearly celebration of love. The ensemble cast is a who’s who of Hollywood superstars, with Jessica Alba, Topher Grace, Jennifer Garner, Ashton Kutcher, Jessica Biel, Bradley Cooper, Shirley MacLaine, Jamie Foxx, Julia Roberts, Patrick Dempsey, and Anne Hathaway all making an appearance. It’s also notable for being Taylor Swift’s first acting role (she should stick to singing).
10. Bridget Jones’ Diary
A hilarious look at the life of 32-year-old English woman Bridget Jones and her attempts at navigating the dating field. Spawning two so-so sequels, the original is certainly the best of the three. Renée Zellweger is wonderful as Jones’, a modern woman struggling to find Mr. Right who suddenly finds herself dealing with two men vying for her attention.
11. The Big Sick
One of the best movies to come out of 2017, The Big Sick is loosely based on actor Kumail Nanjiani and wife Emily V. Gordon’s courtship. The film centers on the clash of cultures between Kumail and Emily’s (Zoe Kazan) families when Emily gets sick. Incredibly funny and heartwarming, The Big Sick is a modern rom-com sure to be a hit with your loved one.
12. 50 First Dates
Remember when Adam Sandler made funny movies? 50 First Dates is one of the last good Sandler films thanks to a unique premise and some great acting from Sandler, Drew Barrymore, and Sean Austin. Sandler plays a womanizer who falls for Barrymore and must try and win her over day after day after discovering she suffers from amnesia. Brilliant stuff.
13. Sleepless in Seattle
Another classic, Sleepless in Seattle stars Tom Hanks and Meg Ryan as a “will they, won’t they” duo who repeatedly run into each other over the course of the movie. It’s a sappy affair well suited to Hanks and Ryan and sure to have your partner cozying up to you on the couch.
14. Magic Mike
Sure, this film doesn’t have a lot to do with Valentine’s Day, but it’s sure to keep your partner satisfied. Based on Channing Tatum’s early days as a male stripper, Magic Mike is a tongue in cheek look at what goes on behind the scenes. It’s not just half-naked men either, with a sweet love story between Tatum and Cody Horn at the movie’s core. Matthew McConaughey also steals every scene he’s in as former stripper Dallas.
15. Pretty Woman
Universally loved, Pretty Woman is a sure-fire crowd-pleaser. A modern-day Cinderella tale, the movie explores the relationship between Richard Gere’s businessman and Julia Roberts’ lady of the night. The chemistry between Gere and Roberts is surprisingly electric, with Pretty Woman in the romcom hall of fame.
16. The Spectacular Now
Remember when you first fell in love? The Spectacular Now perfectly captures the innocence and naivety of what it feels like to fall in love for the first time. High school seniors Aimee (Shailene Woodley) and Sutter (Miles Teller) come from different sides of the tracks, but this doesn’t stop them from becoming lovers. The two must confront their fears and family issues in order to keep their relationship alive in this engaging coming of age story.
17. Friends with Benefits
While the title might not lend itself to a romantic movie night, Freinds with Benefits is a well-written flick about the pitfalls of platonic sex. Justin Timberlake and Mila Kunis are great eye candy while Woody Harrelson, Jenna Elfman, Richard Jenkins, and Patrica Clarkson provide fantastic support.
18. Before Sunrise
Before Sunrise is a 90s indie classic about American Jesse (Ethan Hawke) and French woman Celine (Julie Delpy) who meet on a train and spend the night in Vienna falling in love. It’s chock full of incredible dialogue and directed masterfully by Richard Linklater. If you’re in for the long haul I recommend watching the entire trilogy, but if you’ve only time for one, start here.
19. Garden State
While it has been retrospectively derided by critics, Garden State is a cute indie flick about growing up and finding love when you least expect it. Zach Braff, who also wrote and directed the movie, stars as a struggling actor who returns home after the death of his mother. He reconnects with his high school friends, falls in love with Natalie Portman, and tries to repair his strained relationship with his father. The soundtrack is also awesome.
20. 10 Things I Hate About You
Another Shakesphere adaptation, 10 Things I Hate About You turned the late great Heath Ledge into a bonafide movie star. A modern take on The Taming of the Shrew set around a 90s high school, this has everything you want from a romcom. The script is smartly written, the cast chock full of young, cool talent (Julie Stiles, Joesph Gordan-Levitt, Gabrielle Union, and David Krumholtz), and the laughs plentiful.
21. Crazy, Stupid, Love
Ryan Gosling is a suave ladies man who teaches recently separated Steve Carrell how to pick up chicks in this 2011 movie. Things go down the gurgler when Gosling begins dating Emma Stone, who just happens to be Carrell’s daughter. Features a great support cast including Kevin Bacon, Marias Tomei, and Julianne Moore.
22. Love & Basketball
This one’s got something for everyone; sports for the lads and romance for the ladies. Monica Wright (Omar Epps) and Quincy McCall (Sanaa Lathan) are childhood sweethearts both striving to make it as professional basketball players. The film charts the pair’s relationship as they drift apart chasing their dreams before being reuniting when they both turn pro.
Grossing over $1.8 billion worldwide and transforming Leonardo DiCaprio into a leading man, there’s not much more that needs to be said about Titanic. The tragic sinking of the hulking ship is the background to DiCaprio and Kate Winslet’s whirlwind romance. I still think there was room for two of them on that plank of debris.
24. Brokeback Mountain
Probably not everyone’s cup of tea, but there’s no denying this is a great film. Heath Ledger and Jake Gyllenhaal are phenomenal as two cowboys who develop an intimate relationship and then must deal with the emotional fallout. The movie is also responsible for the Willie Nelson classic, “He Was a Friend of Mine.”
If someone asked me to tell them what Ghost is about, I’d say “Patrick Swayze, Demi Moore, and a pottery wheel.” Of course, there is a bit more to this sensual tale of lost love that includes murder, a psychic, and plenty of action, but the pottery scene is what most people remember. Swayze is in career-best form while Moore and comedian Whoppi Goldberg provide great support. Definitely, one to keep the missus happy and maybe even get her in the mood.
26. The Wedding Singer
Adam Sandler features two times on this list, with The Wedding Singer another laugh out loud comedy from the former SNL star. Set in the 80s, Sandler’s wedding singer is left heartbroken until he meets Drew Barrymore. Unfortunately, she’s engaged, but the two begin to fall for each other and must decide if they want to be together. Throw in a great 80s soundtrack, a fantastic support cast (Christine Taylor, Steve Buscemi, and Allen Covert), and a cameo from Billy Idol and you have yourselves an excellent date night film.
27. (500) Days Of Summer
Here’s another tearjerker best watched with someone you’ve known for longer than 500 days. The movie charts the up and down relationship between Joseph Gordan-Levitt and Zooey Deschanel. It uses a non-linear narrative (offering something different) and a great indie soundtrack featuring The Smiths, Regina Spektor, Hall & Oats, and The Temper Trap.
28. Pride & Prejudice
Why not get some culture and impress your lady friend with your knowledge of Jane Austin by watching this enjoyable adaptation of Pride & Prejudice. Matthew Macfayden and Keira Knightley star as Mr. Darcy and Elizabeth Bennet, with the film straying slightly from the source novel to give it a more life-like feel.
29. The Fault in Our Stars
Grab the tissues, this one will have both you and your partner bawling your eyes out. When cancer patient Hazel (Shailene Woodley) is forced to attend a support group by her parents, she meets fellow cancer suffer Gus (Ansel Elgort). The two quickly bond and fall in love. The movie follows the duo’s journey as they battle cancer while finding out what real love is.
30. Bull Durham
This one is a personal selection. Part sports film, part romance, Bull Durham finds Kevin Costner playing a washed-up pitcher traded in by the Durham Bulls to help rookie Tim Robbins. Robbins soon falls for baseball groupie Susan Sarandon, but when sparks fly between Costner and Sarandon, things heat up both on and off the pitch. One of Costner’s best roles.
Will Smith plays a smooth-talking dating coach who is hired by Kevin James to help him win over the woman of his dreams. While doing so Smith falls for gossip columnist Eva Mendes, who is immune to his charms. Hilarity ensues.