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How to Be Single poster

Movies that feel likeHow to Be Single (2016)

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.

If you loved How to Be Single, the closest films we have are Obvious Child (2014), Trainwreck (2015) and To All the Boys: P.S. I Still Love You (2020). All three share How to Be Single'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).

🍅 45% Rotten Tomatoes★ 6.1 IMDb ↗TMDB ↗dir. Christian Ditterwittyplayfulromantic
9 of 12 streaming nowNetflix · HBO Max · Amazon Prime Video

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If How to Be Single hit the spot, these will too

Obvious Child poster
Obvious Child
2014 · dir. Gillian Robespierre
🍅 90%★ 6.7comedy · romance

Both rooted in New York City

The difference: Reviewed even better

An immature, newly unemployed comic must navigate the murky waters of adulthood after her fling with a graduate student results in an unplanned pregnancy.

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

Both are built on the same subject: one-night stand

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.

To All the Boys: P.S. I Still Love You poster
To All the Boys: P.S. I Still Love You
2020 · dir. Michael Fimognari
🍅 78%★ 6.1romance · comedyNetflix

The same mix in both: wit, then play

Lara Jean and Peter have just taken their romance from pretend to officially real when another recipient of one of her love letters enters the picture.

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

Both lean on romance more than on comedy

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

Crazy Rich Asians poster
Crazy Rich Asians
2018 · dir. Jon M. Chu
🍅 91%★ 6.9comedy · romanceMax

Romance built on wit, twice over

An American-born Chinese economics professor accompanies her boyfriend to Singapore for his best friend's wedding, only to get thrust into the lives of Asia's rich and famous.

The Perfect Date poster
The Perfect Date
2019 · dir. Chris Nelson
🍅 67%★ 5.8romance · comedyNetflix

Comedy with a pulse of play, in both cases

No beau? No problem! To earn money for college, a high schooler creates a dating app that lets him act as a stand-in boyfriend.

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

One thread runs through both: 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

The same preoccupation in both: single

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.

Valentine's Day poster
Valentine's Day
2010 · dir. Garry Marshall
🍅 18%★ 5.8comedy · romance

Romantic romance, and it commits to that

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

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

Witty comedy in both cases

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.

A Rainy Day in New York poster
A Rainy Day in New York
2019 · dir. Woody Allen
🍅 46%★ 6.4comedy · romancePrime Video

Playful romance, and it commits to that

Two young people arrive in New York to spend a weekend, but once they arrive they're met with bad weather and a series of adventures.

What's Your Number? poster
What's Your Number?
2011 · dir. Mark Mylod
🍅 23%★ 6.1comedy · romanceNetflix

Both run romantic where it counts

Ally Darling is realizing she's a little lost in life. Her latest romance has just fizzled out, and she's just been fired from her marketing job. Then she reads an eye-opening magazine article that warns that 96 percent of women who've been with 20 or more lovers are unlikely to find a husband. Determined to turn her life around and prove the article wrong, Ally embarks on a mission to find the perfect mate from among her numerous ex-boyfriends.

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The best-reviewed films that share How to Be Single’s defining feeling.