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27 Dresses poster

Movies that feel like27 Dresses (2008)

Altruistic Jane finds herself facing her worst nightmare as her younger sister announces her engagement to the man Jane secretly adores.

If you loved 27 Dresses, the closest films we have are Trainwreck (2015), Zack and Miri Make a Porno (2008) and My Best Friend's Wedding (1997). All three share 27 Dresses' 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).

🍅 41% Rotten Tomatoes★ 6.2 IMDb ↗TMDB ↗dir. Anne Fletcherwittyplayfulromantic
9 of 12 streaming nowNetflix · Disney Plus · Apple TV

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If 27 Dresses hit the spot, these will too

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

Common ground: romcom

The difference: Reviewed even better

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

The same mix in both: wit, then play

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.

My Best Friend's Wedding poster
My Best Friend's Wedding
1997 · dir. P.J. Hogan
🍅 75%★ 6.4comedy · romanceParamount+

The same preoccupation in both: new love

When she receives word that her longtime platonic pal Michael O'Neal is getting married to debutante Kimberly Wallace, food critic Julianne Potter realizes her true feelings for Michael -- and sets out to sabotage the wedding.

The Proposal poster
The Proposal
2009 · dir. Anne Fletcher
🍅 45%★ 6.8comedy · romance · drama

Anne Fletcher directing both, with the same fingerprints on each

The difference: Leans harder into drama than 27 Dresses does

When she learns she's in danger of losing her visa status and being deported, overbearing book editor Margaret Tate forces her put-upon assistant, Andrew Paxton, to marry her.

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.

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

Romantic comedy in both cases

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.

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

One thread runs through both: bride

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.

The Break-Up poster
The Break-Up
2006 · dir. Peyton Reed
🍅 34%★ 5.8romance · comedyStarz

Both keep coming back to the same thing: new love

Pushed to the breaking-up point after their latest 'why can't you do this one little thing for me?' argument, Brooke calls it quits with her boyfriend Gary. What follows is a hilarious series of remedies, war tactics, overtures and undermining tricks – all encouraged by the former couple's friends and confidantes …and the occasional total stranger! When neither ex is willing to move out of their shared apartment, the only solution is to continue living as hostile roommates until one of them reaches breaking point.

What Happens in Vegas poster
What Happens in Vegas
2008 · dir. Tom Vaughan
🍅 25%★ 6.1comedy · romance

Both lean on wit more than on romance

During a wild vacation in Las Vegas, career woman Joy McNally and playboy Jack Fuller come to the sober realization that they have married each other after a night of drunken abandon. They are then compelled, for legal reasons, to live life as a couple for a limited period of time. At stake is a large amount of money.

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

Comedy built on play, twice over

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.

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

Romantic romance, and it commits to that

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.

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

Comedy with a pulse of wit, in both cases

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.

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The best-reviewed films that share 27 Dresses’ defining feeling.