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Valentine's Day poster

Movies that feel likeValentine's Day (2010)

Intertwining couples and singles in Los Angeles break-up and make-up based on the pressures and expectations of Valentine's Day.

If you loved Valentine's Day, the closest films we have are Pretty Woman (1990), The Holiday (2006) and Trainwreck (2015). All three share Valentine's Day's witty and playful feel, which is what we rank on before quality.

Seen the big three already? The under-the-radar pick below is Set It Up (2018).

🍅 18% Rotten Tomatoes★ 5.8 IMDb ↗TMDB ↗dir. Garry Marshallwittyplayfulromantic
8 of 12 streaming nowNetflix · Hulu · Disney Plus

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See it on the Mood Map

If Valentine's Day hit the spot, these will too

Pretty Woman poster
Pretty Woman
1990 · dir. Garry Marshall
🍅 65%★ 7.1romance · comedy

Garry Marshall directing both, with the same fingerprints on each

The difference: Critics rated this one higher still

Vivian is a carefree, streetwise diamond in the rough when she meets sophisticated billionaire Edward in a chance encounter that turns into a week-long business arrangement. But Vivian's energetic spirit challenges Edward's no-nonsense approach to life, and soon they are teaching each other – and falling in love!

The Holiday poster
The Holiday
2006 · dir. Nancy Meyers
🍅 51%★ 7comedy · romanceHulu

Common ground in both: holiday and multiple storylines

Two women, one American and one British, swap homes at Christmastime following bad breakups. Each woman finds romance with a local man but realizes that the imminent return home may end the relationship.

Trainwreck poster
Trainwreck
2015 · dir. Judd Apatow
🍅 84%★ 6.2comedy · romance

The same preoccupation in both: romcom

Ever since her father drilled into her head that monogamy isn't realistic, magazine writer Amy has made promiscuity her credo. As much as she enjoys an uninhibited life free of commitment, Amy is really in a rut. While writing a profile about charming and successful sports doctor Aaron Conners, she finds herself actually falling in love for the first time -- and what's more, Aaron seems to really like her too. Amy starts to wonder if it's time to clean up her act and face her fears.

Zack and Miri Make a Porno poster
Zack and Miri Make a Porno
2008 · dir. Kevin Smith
🍅 65%★ 6.5comedy · romance

Witty where it counts, playful underneath

Lifelong platonic friends Zack and Miri look to solve their respective cash-flow problems by making an adult film together. As the cameras roll, however, the duo begin to sense that they may have more feelings for each other than they previously thought.

Set It Up poster
Set It Up
2018 · dir. Claire Scanlon
🍅 92%★ 6.5romance · comedyNetflix

Both are built on the same subject: romcom

Two overworked and underpaid assistants come up with a plan to get their bosses off their backs by setting them up with each other.

Mamma Mia! Here We Go Again poster
Mamma Mia! Here We Go Again
2018 · dir. Ol Parker
🍅 80%★ 6.6comedy · romanceRent or buy

Comedy with a pulse of romance, in both cases

Five years after meeting her three fathers, Sophie Sheridan prepares to open her mother’s hotel. In 1979, young Donna Sheridan meets the men who each could be Sophie’s biological father.

How to Be Single poster
How to Be Single
2016 · dir. Christian Ditter
🍅 45%★ 6.1comedy · romance

Both keep coming back to the same thing: single

New York City is full of lonely hearts seeking the right match, and what Alice, Robin, Lucy, Meg, Tom and David all have in common is the need to learn how to be single in a world filled with ever-evolving definitions of love.

The Ugly Truth poster
The Ugly Truth
2009 · dir. Robert Luketic
🍅 14%★ 6.4comedy · romance

One thread runs through both: valentine's day

A romantically challenged morning show producer is reluctantly embroiled in a series of outrageous tests by her chauvinistic correspondent to prove his theories on relationships and help her find love. His clever ploys, however, lead to an unexpected result.

Confessions of a Shopaholic poster
Confessions of a Shopaholic
2009 · dir. P.J. Hogan
🍅 26%★ 5.9comedy · romanceDisney+

Witty romance, and it commits to that

In the glamorous world of New York City, Rebecca Bloomwood is a fun-loving girl who is really good at shopping – a little too good, perhaps. She dreams of working for her favorite fashion magazine, but can't quite get her foot in the door – until ironically, she snags a job as an advice columnist for a financial magazine published by the same company.

Along Came Polly poster
Along Came Polly
2004 · dir. John Hamburg
🍅 27%★ 6comedy · romanceParamount+

Both lean on play more than on comedy

Reuben Feffer is a guy who's spent his entire life playing it safe. Polly Prince is irresistible as a free-spirit who lives for the thrill of the moment. When these two comically mismatched souls collide, Reuben's world is turned upside down, as he makes an uproarious attempt to change his life from middle-of-the-road to totally-out-there.

I Now Pronounce You Chuck & Larry poster
I Now Pronounce You Chuck & Larry
2007 · dir. Dennis Dugan
🍅 15%★ 5.9comedy · romanceStarz

Common ground: single

Firefighters Chuck Ford and Larry Valentine are guy's guys, loyal to the core—which is why when widower Larry asks Chuck to pose as his lover so that he can get domestic partner benefits for his kids, his buddy agrees. However, things get dicey when a bureaucrat comes calling, and the boys are forced to present a picture of domestic bliss.

Holidate poster
Holidate
2020 · dir. John Whitesell
🍅 45%★ 6.2comedy · romanceNetflix

Common ground: holiday

Fed up with being single on holidays, two strangers agree to be each other's platonic plus-ones all year long, only to catch real feelings along the way.

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The best-reviewed films that share Valentine's Day’s defining feeling.