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Movies that feel like 27 Dresses (2008)

If you loved 27 Dresses, the closest films we have are The Proposal (2009), Along Came Polly (2004) and The Break-Up (2006). All three share 27 Dresses' witty and playful feel, which is what we rank on before quality. 5 of the 12 picks below are included with a subscription right now on Amazon Prime Video, Hulu and Paramount Plus Premium and others, checked against today's data.

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

🍅 41% Rotten Tomatoes6.1 IMDb ↗TMDB ↗dir. Anne Fletcherwittyplayfulromantictender
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If 27 Dresses hit the spot, these will too

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.

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Along Came Polly poster
Along Came Polly
2004 · dir. John Hamburg
🍅 27%6comedy · romance

The same two preoccupations: bride, and romcom

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.

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

One thread runs through both: 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.

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

Both keep coming back to the same thing: romcom

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.

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

Witty where it counts, playful underneath

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

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

Romantic and tender in the same breath

The difference: Reviewed a good deal more coolly

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

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.

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Blended poster
Blended
2014 · dir. Frank Coraci
🍅 15%6.5comedy · romance

Comedy built on wit, twice over

Recently divorced mom Lauren and widowed dad Jim let their friends push them into a blind date, which goes disastrously wrong. Unsurprisingly, neither wants to see the other ever again. However, fate intervenes when both Jim and Lauren, unbeknownst to each other, purchase one-half of the same vacation package at a South African resort for families, during spring break. They and their children are forced to share the same romantic suite and participate in a slew of family activities together.

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How to Lose a Guy in 10 Days poster
How to Lose a Guy in 10 Days
2003 · dir. Donald Petrie
🍅 42%6.5comedy · romance

Both lean on play more than on romance

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!

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Notting Hill poster
Notting Hill
1999 · dir. Roger Michell
🍅 84%7.2romance · comedy

Romantic comedy, and it commits to that

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.

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Anyone but You poster
Anyone but You
2023 · dir. Will Gluck
🍅 53%6.1romance · comedy

Tender romance in both cases

After an amazing first date, Bea and Ben’s fiery attraction turns ice cold — until they find themselves unexpectedly reunited at a destination wedding in Australia. So they do what any two mature adults would do: pretend to be a couple.

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Mamma Mia! Here We Go Again poster
Mamma Mia! Here We Go Again
2018 · dir. Ol Parker
🍅 80%6.6comedy · romance

Comedy with a pulse of wit, 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.

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