10 Movies to Watch if You Love Valentine’s Day

February 15, 2019

Let’s admit it: Valentine’s Day is a polarizing holiday. Depending on who you are, it can be a day of romance and roses or contrived and commercialized. Regardless of how you plan on spending the day, I’ve compiled a list of ten corny, heartwarming romantic comedies to indulge in. And if you hate Valentine’s Day? Well, there’s a list for you too!

01. My Best Friend’s Wedding (1997)

When Julianne’s best friend Michael announces he’s engaged, Julianne suddenly realizes that she’s actually in love with him. While she vows to stop the wedding at all costs, things get more complicated when she becomes the bride’s maid of honor. My Best Friend’s Wedding is a fun anti-rom com that proves not all happy endings need to be romantic, and not all rom-com heroines get what they want.

02. Sleepless in Seattle (1993)

A year after his mom’s death, young Jonah Baldwin calls into a Seattle radio show lamenting that his lonely dad Sam (Tom Hanks), needs a new wife. After hearing Sam on the radio, Annie (Meg Ryan) feels drawn to the widower and writes him a letter asking him to meet her at the top of the Empire State Building on Valentine’s Day.

03. Say Anything… (1989)

After their high school graduation, sensitive and noble Lloyd Dobbler sets out to win the heart of his dream girl, valedictorian good girl Diane Court. John Cusack and Ione Skye are magical together in this coming-of-age romance, complete with the iconic boom box scene and Peter Gabriel’s swoon-worthy In Your Eyes.

04. The Philadelpia Story (1940)

Tracy (Katherine Hepburn) is about to walk down the aisle for a second time when she happens to cross paths with both her ex-husband (Cary Grant) and a tabloid reporter (Jimmy Stewart), leading Tracy to question who she is, what she wants and who she truly loves. A classic rom-com love triangle with three iconic legends.

05. Before Sunset (2004)

The second in the Before Trilogy, Before Sunset finds Jesse and Celeste reconnecting nine years after the events of Before Sunrise. Jesse has written a book about their magical night in Vienna, and the two talk about how that encounter changed their lives.

06. Set It Up (2018)

Two overworked assistants, Harper (Zoey Deutch) and Charlie (Glen Powell), work together to get their demanding bosses off their backs by setting them up with each other. From co-conspirators to friends to maybe something more, the chemistry between Zoey and Glen helped make Set It Up one of the genre’s rare highlights of the past few years.

07. While You Were Sleeping (1995)

A lonely woman named Lucy (Sandra Bullock) saves her crush (Peter Gallagher) from an oncoming train, and following a misunderstanding, his family believes they’re engaged. While he lies in a coma, Lucy begins to fall for his brother Jack (Bill Pullman) instead. Sweet, funny, and romantic with a hilarious supporting cast.

08. Definitely, Maybe (2008)

Will (Ryan Reynolds) is in the midst of a divorce when his daughter Maya (Abigail Breslin) asks him to tell her how he met her mother. Will’s tale includes three lovely, enchanting women who have affected his life differently. But the question remains, which of Will’s three greatest loves is Maya’s mother?

09. Isn’t It Romantic? (2019)

Isn’t It Romantic is quick to inform us that “Life is not a fairy tale.” But this hilarious, heartwarming takedown of rom-coms and their cheesy tropes is one of the perfect movies to watch on the most romantic day of the year. Rebel Wilson is perfectly cast as a cynical woman who discovers the importance of self-love.

10. Sleeping With Other People (2015)

What happens when two sex-obsessed people who fear intimacy become best friends? You get a movie like Sleeping With Other People, a criminally underrated romantic comedy starring Alison Brie and Jason Sudeikis, whose chemistry is off the charts. Funny, sexy, and heartfelt, this is a friend to lovers movie that deserves multiple viewings!