10 Movies to Watch If You Love Valentine's Day

by - February 09, 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 it can feel 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!

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 magic together in this coming of age romance, complete with the iconic boom box scene and Peter Gabriel's swoon-worthy In Your Eyes.

Sleepless In Seattle (1993)
A year after the death of his mom, 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.

The Philadelphia 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.

My Best Friend's Wedding (1997)
Julianne Potter (Julia Roberts) and her best friend Michael (Dermot Mulroney) made a pact to marry if they're both still single at 28. But just before her 28th birthday, Michael tells Julianne he's engaged to Kimmy (Cameron Diaz), a beautiful, perky blonde. Jealousy takes hold and Julianne plots to break up the wedding and take the groom for herself.

Before Sunrise (1995)
Jesse (Ethan Hawke), an American on his way to Vienna, meets Celine (Julie Delpy) on his train. She's headed for Paris, but the two forge a surprising connection, leading Jesse to convince her to get off the train with him Vienna, both of them aware that this is likely to be their only night spent together before parting ways. This sweet romance was the first in the Before Trilogy, followed by Before Sunset and Before Midnight.

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 Harper and Glen helped make Set It Up one of the genre's rare highlights of the past few years.

While You Were Sleeping (1995)
A lonely woman named Lucy (Sandra Bullock) saves her crush (Peter Gallagher) from an oncoming train and a misunderstanding that follows has his family believing 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.

Definitely, Maybe (2008)
Will (Ryan Reynolds) is in the midst of a divorce when his daughter Maya (Abigail Breslin) asks him to tell her the story of how he met her mother. Will's tale includes three very beautiful, very enchanting women who have affected his life in very different ways. But the question remains, which of Will's three greatest loves is Maya's mother?

The Shop Around The Corner (1940)
Alfred (Jimmy Stewart) and Klara (Margaret Sullivan) are employees at a general store in Budapest. They're constantly butting heads and at odds with one another. They're also completely unaware that they're each other's pen pals, whom they're both incredibly enamored with. A charming, funny romance that inspired 1998's You've Got Mail.

When Harry Met Sally (1989)
What 'must watch' list would be complete without When Harry Met Sally? One of the genre's best, WHMS tells the tale of two strangers (Meg Ryan and Billy Crystal) who share a contentious car ride from Chicago to New York, and then over the course of the next decade form a friendship laden with romantic tension. The true question here is, can two friends sleep together and still be friends in the morning? This movie is close to perfection.

Hate Valentine's Day? I've got you covered there too! Below are five anti-Valentine's Day films to curl up on the couch and enjoy.

The Break Up (2006)
When Brooke (Jennifer Aniston) and Gary (Vince Vaughn) call it quits, neither is willing to move out of their condo. After mean spirited revenge tactics fail to get the other to concede defeat, Brooke and Gary resort to becoming hostile roommates instead.

The First Wives Club (1996)
After a friend commits suicide over her ex-husband's new marriage to a younger woman, three women (Diane Keaton, Goldie Hawn, and Bette Midler) reunite and make a pact to get revenge on their own exes for taking them for granted and treating them poorly.

Fatal Attraction (1987)
Despite being happily married, Dan (Michael Douglas) has a one night stand with a sexy book editor (Glenn Close) who becomes increasingly and dangerously unstable after Dan jilts her.

Nappily Ever After (2018)
Not entirely anti-love, but after a mishap at the salon and a botched birthday party where she expected a proposal from her longtime boyfriend, Violet (Sanaa Lathan) finds herself single and confused about where her life is supposed to go next. A great dramedy about finding purpose without the perfect man, or the perfect hair.

The War of the Roses (1989)
Like The Break Up, after a couple decides to split up, both fight for ownership of their grand home, leading to a brutally vicious battle that leaves their home, and family, in shambles. A dark comedy about the perfect marriage gone wrong.

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  1. I NEVER saw "While You Were Sleeping" so maybe I finally will on Thursday! Sandra Bullock is always so likable and so is Pullman. I love War of the Roses, it's such a brilliant dark comedy!

    1. I can watch Sandra is just about anything. WYWS could (probably) never be made today, but it's such a sweet story. I hope you enjoy it! and I remember watching War of the Roses with my parents when I was younger and being traumatized by the ending. I love it now, as an adult. I don't know what that means! lol

  2. Oh, War of the Roses. My parents loved that film as do I. That is perfect!

    1. Michael Douglas and Kathleen Turner are so good in it! I may need to rewatch it again soon.


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