20 movies to watch in honor of Valentine's Day

From comedy to calamity, we put together a list of some of our favorite movies about love in honor of the holiday.

Casablanca

The Notebook

Love it or hate it, "The Notebook" has, in our opinion, officially entered the romance movie canon. We doubt you need a recap but just in case, the film stars Ryan Gosling as a poor man who works in a lumber mill and Rachel McAdams as the wealthy woman who falls for him. They're separated by World War II and then are reunited later in life...and find it's never too late for love.

To All the Boys I've Loved Before

In this super sweet 2018 Netflix film, we see Lara Jean, played by Lana Condor, learn to loosen up and fall in love — first, as part of an act and then later, for real. Between some super sweet high school moments, scenic Portland and the adorable Noah Centineo as her love interest Peter, we're fans.

Clueless

An absolute classic, this 1995 film follows shallow Beverly Hills high school student Cher, played by Alicia Silverstone. She and her friend Dionne, played by Stacey Dash, take on a classic makeover project in Tai, played by Brittany Murphy. Perennial favorite Paul Rudd plays Cher's former stepbrother and later love interest in a very sweet coming-of-age story with a lesson about being a good person. 

27 Dresses

Oh "27 Dresses." We're ignoring the fact the plot essentially revolves around the phrase "forever a bridesmaid, never the bride" and that the movie was promoted with the tagline "She's about the find the perfect fit." It came out in 2008, which wasn't really a different time, but it's fine.
That said, it's a great watch starring Katherine Heigl falling for a cynical journalist who covers weddings, played by James Marsden. There's karaoke, a love triangle, and a classic betrayal/misunderstanding before a happy ending.

"A Good Year"

"A Good Year" stars Russell Crowe — yes, that Russell Crowe — as a jerk who works in finance. He ends up inheriting a winery from an uncle he was once close with and (after conveniently getting in trouble at work) he spends some time there to learn a valuable lesson about life, love, and so on. There's kissing in the rain, French vineyards, and a classic will-they-or-won't-they storyline we all watch these kinds of movies for.

"Letters to Juliet"

Just in time for Taylor Swift to release a new version of this film's theme song, "Love Story," you can watch this 2010 film starring Amanda Seyfried as Sophie, engaged to a guy who like, really loves Italian food, played by Gael García Bernal.
Sophie finds an old letter written to "Juliet" in a wall in Verona and decides to respond. The woman, now a grandmother, responds by coming to Italy to find her Romeo and brings her handsome and cynical grandson, Charlie, played by Christoper Egan. So the plot is a little unlikely but you know what? It's charming, there's loads of footage of the gorgeous Italian countryside, and who doesn't love love?

Notting Hill

In this 1999 classic, Hugh Grant plays a divorced travel bookshop owner who, by chance, meets a fabulous celebrity played by Julia Roberts. However unlikely they are as a couple in the film, it's a sweet story about how true love conquers all and what's not to love during these ~uncertain times?~

Love Actually

This is another one of those love it or hate it films, but 2003's "Love Actually" is sort of part of the romance film canon. The movie tracks the lives of eight couples who are loosely connected in London just before Christmas. There are some questionable moments — say, for example, when one character makes a move on his best friend's wife holding signs in front of the door — but you can still watch a film while acknowledging its problematic aspects. Plus, Hugh Grant as prime minister!  

50 First Dates

In this 2004 film, we see Drew Barrymore as an art teacher who, after a freak accident, forgets the events of the day prior by the time she wakes up. She meets Adam Sandler, a womanizing marine life veterinarian, who falls for her and takes it upon himself to woo Barrymore each and every day. Set in Hawaii, there are hijinks and heartfelt moments with a happy ending.

The Proposal

High strung book publisher Margaret Tate, played by Sandra Bullock, is about to be deported to Canada when she comes up with a quick solution to her problem: getting married. The only issue is that she's perpetually single so she convinces/blackmails her assistant, Andrew Paxton, played by the always-charming Ryan Reynolds, to marry her.

The two embark on a journey back to Paxton's hometown in Alaska to meet his parents (Mary Steenburgen and Craig T. Nelson) and iconic Grandma Annie, played by Betty White. There's rapping with Betty White in the woods, misunderstandings, stunning Alaska scenery and a shirtless Ryan Reynolds...definitely worth a watch.

Love & Basketball

This 2000 film follows the story of  two friends, Monica and Quincy, who grow up together playing basketball. As they get older, they realize they should be together, but family drama leads to their early breakup. Eventually, they find their way back to each other again.

About Time

If you're looking for a Rachel McAdams film that isn't "The Notebook," check out 2013's "About Time." Starring Domhnall Gleeson as the awkward Tim who finds at the age of 21 he can time travel, he uses his gift to fall in love with McAdams' character Mary. Like most time travel films, it explores the benefits and drawbacks of time travel, but it also features a very sweet love story between the lead characters.

Along Came Polly

This underrated 2004 rom-com starring Ben Stiller and Jennifer Aniston features Stiller as uptight risk assessment manager Ruben. His new wife, played by Debra Messing of "Will and Grace" fame, cheats on him on their honeymoon, so Ruben comes home to New York alone and at a crossroads. He bumps into his former classmate Polly, played by Aniston, and discovers that while you can analyze risk sometimes you just have to take a leap of faith.

The Big Sick

Based loosely on comedian Kumail Nanjiani's real life, "The Big Sick" stars Kumail as a version of himself, pre-fame, living in Chicago and doing stand-up comedy. He meets his love interest, Emily, played by Zoe Kazan, at one of his shows when she heckles him and they start hanging out. Kumail can't tell his family about Emily because he's afraid they will disapprove of him dating someone outside their culture and then Emily gets so sick she has to be put in a coma. No spoilers, but this is a really sweet story with a fresh twist on the classic family-keeping-the-leads apart trope.

Southside with You

This 2016 film details the story of how then-future President Barack Obama won Michelle Obama’s heart in 1989 on a hot afternoon on the South Side of Chicago. Of course, we can assume they took a little poetic license with the tale, but the result is a sweet film about finding the one.

I Love You, Man

This 2009 rom com (honestly, really more of a comedy with a side note of romance) stars Paul Rudd as blushing groom Peter in need of more close male friends to fill out his wedding party. Specifically, he really needs a best man. Peter sets out to find one and befriends Sydney. Their ensuing friendship, with all its ups and downs, makes the film hilarious and ends with a dramatic (non-romantic) gesture that really rounds out the entire film.

P.S. I Love You

Before Gerry, played by Gerard Butler, died, he planned ahead. He wrote his wife, Holly, played by Hilary Swank, letters for her 30th birthday that would apparently help ease her grief and encourage her to move forward. There's sweeping vistas of Ireland, slightly weird ghost Gerard Butler, and also scenes in New York City, so what's not to love?

Shakespeare in Love

This 1998 period romantic dramedy stars Joseph Fiennes as the young Bard himself and Gwyneth Paltrow as his love interest, who dresses as a man to get a role in what would become one of Shakespeare's most famous plays: "Romeo and Juliet."

My Big Fat Greek Wedding

It’s one of the classic rom-com tropes: an overbearing family doesn’t approve of the protagonist’s chosen partner for one reason or another. In “My Big Fat Greek Wedding,” Nia Vardalos plays Toula, who falls for a non-Greek man, Ian, played by John Corbett. Of course, they find that love always finds a way.

Pretty Woman

This film took second place in TODAY's 2021 best rom-com bracket!
The 1990 movie is about a businessman, played by Richard Gere, who hires an escort, played by Julia Roberts, to bring to events. One thing leads to another and they fall in love.

You've Got Mail

This 1998 Meg Ryan-Tom Hanks classic won TODAY's rom-com bracket, capturing 53% of nearly 10,000 votes. The film features Hanks as the owner of a big bookstore chain and Ryan is the woman he falls for online...only to realize she runs the small business he's trying to take over.