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How to Lose a Guy in 10 Days poster

Movies that feel likeHow to Lose a Guy in 10 Days (2003)

It's the battle of wills, as Andie needs to prove she can dump a guy in 10 days, whereas Ben needs to prove he can win a girl in 10 days. Now, the clock is ticking—and the wildly entertaining comedy smash is off and running in this irresistible tale of sex, lies and outrageous romantic fireworks!

If you loved How to Lose a Guy in 10 Days, the closest films we have are You've Got Mail (1998), Notting Hill (1999) and Definitely, Maybe (2008). All three share How to Lose a Guy in 10 Days' 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).

🍅 42% Rotten Tomatoes★ 6.5 IMDb ↗TMDB ↗dir. Donald Petriewittyplayfulromantic
10 of 12 streaming nowNetflix · Disney Plus · Apple TV

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If How to Lose a Guy in 10 Days hit the spot, these will too

You've Got Mail poster
You've Got Mail
1998 · dir. Nora Ephron
🍅 69%★ 6.7comedy · romanceParamount+

One thread runs through both: romcom

The difference: Critics rated this one higher still

Book superstore magnate Joe Fox and independent book shop owner Kathleen Kelly fall in love in the anonymity of the Internet—both blissfully unaware that he's trying to put her out of business.

Notting Hill poster
Notting Hill
1999 · dir. Roger Michell
🍅 84%★ 7.2romance · comedyParamount+

Both keep coming back to the same thing: a group of friends

London bookstore owner William Thacker's quiet life turns upside down when a chance encounter with famous actress Anna Scott sparks an unlikely romance challenged by their vastly different worlds.

Definitely, Maybe poster
Definitely, Maybe
2008 · dir. Adam Brooks
🍅 71%★ 7.1comedy · romanceApple TV+

Both are built on the same subject: relationship

When Will decides to tell his daughter the story of how he met her mother, he discovers that a second look at the past might also give him a second chance at the future.

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

New York City shapes both of them

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

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

Witty and playful in the same breath

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.

There's Something About Mary poster
There's Something About Mary
1998 · dir. Peter Farrelly
🍅 84%★ 7.1romance · comedy

The same preoccupation in both: romcom

For Ted, prom night went about as bad as it’s possible for any night to go. Thirteen years later, he finally gets another chance with his old prom date, only to run up against other suitors including the sleazy detective he hired to find her.

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

Common ground: relationship

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.

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

Common ground: basketball

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.

What Women Want poster
What Women Want
2000 · dir. Nancy Meyers
🍅 53%★ 6.5comedy · romanceParamount+

Both lean on romance more than on comedy

Advertising executive Nick Marshall is as cocky as they come, but what happens to a chauvinistic guy when he can suddenly hear what women are thinking? Nick gets passed over for a promotion, but after an accident enables him to hear women's thoughts, he puts his newfound talent to work against Darcy, his new boss, who seems to be infatuated with him.

American Pie 2 poster
American Pie 2
2001 · dir. J.B. Rogers
🍅 51%★ 6.5comedy · romance

Both are built on the same subject: a group of friends

After a year apart - attending different schools, meeting different people - the guys rent a beach house and vow to make this the best summer ever. As it turns out, whether that will happen or not has a lot to do with the girls. Between the wild parties, outrageous revelations and yes, a trip to band camp, they discover that times change and people change, but in the end, it's all about sticking together.

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

Witty romance, and it commits to that

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.

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

Playful 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.

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