25 Best Movies like 27 Dresses for Romance and Laughter

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45%

48

6.7

In "The Proposal," Margaret Tate (Sandra Bullock), a high-powered book editor, faces deportation to Canada and impulsively announces she's engaged to her long-suffering assistant, Andrew Paxton (Ryan Reynolds). As they travel to meet Andrew's family for the first time, they navigate a charade of fake romance and real emotions. Similar to "27 Dresses," both films explore the dynamics between professional ambition and personal relationships, with protagonists juggling societal expectations and their own desires for love and fulfillment.

CAST

Sandra Bullock

Ryan Reynolds

Malin Åkerman

Craig T. Nelson

Mary Steenburgen

Betty White

Denis O'Hare

Oscar Nunez

Aasif Mandvi

Michael Nouri

Directed by Anne Fletcher

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64%

57

6.3

"13 Going on 30" follows Jenna Rink (Jennifer Garner), who, after a wish on her 13th birthday, wakes up as a 30-year-old woman in 2004. Facing the challenges of adulthood with the mind of a teenager, Jenna reconnects with her childhood friend Matt (Mark Ruffalo) and navigates love, career, and self-discovery. Like "27 Dresses," this film delves into themes of self-identity and the pursuit of happiness, highlighting the importance of staying true to oneself amidst societal pressures and romantic entanglements.

CAST

Jennifer Garner

Mark Ruffalo

Judy Greer

Andy Serkis

Christa B. Allen

Sean Marquette

Alexandra Kyle

Kathy Baker

Phil Reeves

Lynn Collins

Directed by Gary Winick

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75%

62

6.9

In "The Devil Wears Prada," Andy Sachs (Anne Hathaway) lands a job as an assistant to Miranda Priestly (Meryl Streep), the formidable editor-in-chief of a prestigious fashion magazine. Andy struggles to adapt to the cutthroat fashion industry while maintaining her integrity and personal relationships. Like "27 Dresses," this film explores themes of career aspirations and personal growth, portraying the protagonist's journey towards self-discovery and finding a balance between professional success and personal happiness.

CAST

Anne Hathaway

Meryl Streep

Emily Blunt

Stanley Tucci

Simon Baker

Adrian Grenier

Tracie Thoms

Rich Sommer

Daniel Sunjata

David Marshall Grant

Directed by David Frankel

2 degrees of seperation (similar to The Devil Wears Prada)

from /23 Ultimate Movies Like 'The Devil Wears Prada'

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In "The Holiday," two women, Iris and Amanda, who are dealing with romantic disappointments in their lives, decide to swap homes for the holidays. Iris travels from England to Los Angeles, while Amanda heads to a quaint English countryside. Both women unexpectedly find love in their temporary locations, leading to heartwarming and comedic moments. Similarly to "27 Dresses," "The Holiday" explores themes of love, self-discovery, and the unpredictability of romance, as the characters navigate unexpected connections and personal growth amidst the backdrop of weddings and relationships.

CAST

Cameron Diaz

Kate Winslet

Jude Law

Jack Black

Eli Wallach

Edward Burns

Rufus Sewell

Miffy Englefield

Emma Pritchard

Sarah Parish

Directed by Nancy Meyers

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79%

68

7.4

In "Crazy, Stupid, Love," Cal Weaver's life is turned upside down when he learns that his wife wants a divorce and has been cheating on him. As he navigates single life, he meets Jacob Palmer, a suave bachelor who teaches him the art of dating and seduction. Meanwhile, Cal's son deals with his own romantic troubles, and other characters in their interconnected lives grapple with love in its various forms. Like "27 Dresses," this film intertwines multiple romantic storylines and explores the complexities of love, relationships, and personal growth with a blend of humor and heartfelt moments.

CAST

Steve Carell

Ryan Gosling

Julianne Moore

Emma Stone

Lio Tipton

Jonah Bobo

Joey King

Marisa Tomei

Beth Littleford

John Carroll Lynch

Directed by Glenn Ficarra

2 degrees of seperation (similar to Crazy, Stupid, Love.)

from /25 Heartfelt Movies Like "Crazy, Stupid, Love."

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71%

59

6.4

"Legally Blonde" follows the journey of Elle Woods, a bubbly sorority girl who decides to enroll in Harvard Law School to win back her ex-boyfriend. Despite facing skepticism and stereotypes, Elle proves herself to be a capable and determined student. Along the way, she discovers her true passion for law and surprises everyone, including herself, with her intelligence and tenacity. Similar to "27 Dresses," "Legally Blonde" features a strong and charismatic female protagonist navigating challenges in her personal and professional life while staying true to herself. Both films blend humor with messages of empowerment and self-discovery.

CAST

Reese Witherspoon

Luke Wilson

Matthew Davis

Selma Blair

Victor Garber

Jennifer Coolidge

Ali Larter

Jessica Cauffiel

Alanna Ubach

Holland Taylor

Directed by Robert Luketic

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38%

45

6.2

In "Sweet Home Alabama," Melanie (Reese Witherspoon) is a successful fashion designer in New York City who must confront her past when she returns to her small hometown in Alabama to finalize her divorce from her childhood sweetheart, Jake (Josh Lucas), so she can marry her wealthy fiancé. However, as Melanie navigates the complexities of her old life and new aspirations, she begins to question where her heart truly belongs. Similar to "27 Dresses," this film explores themes of love, identity, and reconciling past relationships, showcasing the protagonist's journey of self-discovery amidst romantic entanglements.

CAST

Reese Witherspoon

Josh Lucas

Patrick Dempsey

Candice Bergen

Mary Kay Place

Fred Ward

Jean Smart

Ethan Embry

Melanie Lynskey

Courtney Gains

Directed by Andy Tennant

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93%

73

7.1

"Enchanted" follows the story of Giselle (Amy Adams), a fairy-tale princess who is banished from her animated kingdom and finds herself in modern-day New York City. As Giselle tries to adapt to the real world and find her way back home, she encounters a divorce lawyer named Robert (Patrick Dempsey) and begins to question her idealized notions of love and happily ever after. Like "27 Dresses," this film blends fantasy elements with romantic comedy, highlighting the clash between fairy-tale romance and real-world complexities while exploring themes of love, acceptance, and self-discovery.

CAST

Amy Adams

Patrick Dempsey

James Marsden

Timothy Spall

Idina Menzel

Rachel Covey

Susan Sarandon

Julie Andrews

Jeff Bennett

Directed by Kevin Lima

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42%

45

6.5

In "How to Lose a Guy in 10 Days," Andie Anderson is a magazine writer tasked with writing an article on how to lose a guy in ten days by exhibiting all the classic behaviors that drive men away. Meanwhile, Benjamin Barry is a successful advertising executive who makes a bet that he can make any woman fall in love with him in ten days. When their paths cross, Andie and Ben find themselves entangled in a hilarious battle of wills as they try to outwit each other while navigating the unpredictable terrain of love and relationships. Similar to "27 Dresses," this film is a romantic comedy that explores the dynamics of modern romance and the challenges of finding true love amidst comedic misunderstandings and unexpected twists.

CAST

Kate Hudson

Matthew McConaughey

Kathryn Hahn

Annie Parisse

Adam Goldberg

Thomas Lennon

Michael Michele

Shalom Harlow

Robert Klein

Bebe Neuwirth

Directed by Donald Petrie

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75%

72

6.8

In "Sleepless in Seattle," widower Sam Baldwin (Tom Hanks) and his young son move to Seattle, where Sam reluctantly opens up about his grief on a radio talk show. Across the country, Annie Reed (Meg Ryan), who's engaged but having doubts, hears Sam's story and becomes captivated. Despite living on opposite coasts, fate seems to intervene as Annie becomes determined to meet Sam. Like "27 Dresses," this film explores the serendipitous nature of love and the idea of two people from different worlds finding each other against the odds, emphasizing the power of fate in bringing people together.

CAST

Tom Hanks

Meg Ryan

Bill Pullman

Ross Malinger

Rosie O'Donnell

Gaby Hoffmann

Rita Wilson

Victor Garber

Rob Reiner

Tom Riis Farrell

Directed by Nora Ephron

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74%

51

6.3

In "My Best Friend's Wedding," Julianne Potter (Julia Roberts) realizes she's in love with her longtime friend Michael (Dermot Mulroney) when he announces his engagement to Kimberly (Cameron Diaz). Julianne embarks on a comedic mission to sabotage the wedding and win Michael's heart. Similar to "27 Dresses," this film delves into themes of unrequited love, friendship, and self-discovery, as Julianne navigates the complexities of her feelings while also grappling with the fear of losing her best friend to someone else.

CAST

Julia Roberts

Dermot Mulroney

Cameron Diaz

Rupert Everett

Christopher Masterson

M. Emmet Walsh

Philip Bosco

Rachel Griffiths

Carrie Preston

Susan Sullivan

Directed by P.J. Hogan

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80%

66

6.8

"Bridget Jones's Diary" follows Bridget Jones (Renée Zellweger), a quirky British woman in her thirties who starts a diary to take control of her life and find love. Along the way, she navigates romantic entanglements with her charming boss Daniel Cleaver (Hugh Grant) and the stoic Mark Darcy (Colin Firth). Like "27 Dresses," this film is a romantic comedy that explores themes of self-discovery, navigating love in the modern world, and the journey towards finding happiness and acceptance, despite the comedic mishaps and challenges along the way.

CAST

Renée Zellweger

Colin Firth

Hugh Grant

Jim Broadbent

Gemma Jones

James Callis

Sally Phillips

Shirley Henderson

Embeth Davidtz

Lisa Barbuscia

Directed by Sharon Maguire

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17%

33

5.3

In "The Wedding Planner," Mary Fiore (Jennifer Lopez) is San Francisco's most successful wedding planner, known for her meticulous attention to detail. Similar to "27 Dresses," Mary is always the one orchestrating beautiful weddings for others while secretly yearning for her own love story. Her life takes an unexpected turn when she falls for the groom of one of her clients, complicating both personal and professional boundaries. Amidst wedding preparations and romantic entanglements, Mary must navigate the complexities of love, loyalty, and self-discovery.

CAST

Jennifer Lopez

Matthew McConaughey

Justin Chambers

Joanna Gleason

Lou Myers

Kathy Najimy

Charles Kimbrough

Judy Greer

Bridgette Wilson-Sampras

Alex Rocco

Directed by Adam Shankman

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15%

36

5.8

"Something Borrowed" follows the intertwined lives of Rachel (Ginnifer Goodwin) and Darcy (Kate Hudson), lifelong best friends with a complicated dynamic. Like "27 Dresses," the film explores the complexities of female friendships and unrequited love. Rachel finds herself in a moral dilemma when she realizes she has feelings for her best friend's fiancé, Dex (Colin Egglesfield). Caught between loyalty to Darcy and her own desires, Rachel must confront her feelings and make difficult choices that will reshape their relationships forever.

CAST

Ginnifer Goodwin

Kate Hudson

Colin Egglesfield

John Krasinski

Steve Howey

Ashley Williams

Geoff Pierson

Jill Eikenberry

Jonathan Epstein

Leia Thompson

Directed by Luke Greenfield

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49%

52

6.4

In "The Princess Diaries," Mia Thermopolis (Anne Hathaway) is an ordinary teenager living in San Francisco, unaware of her royal heritage. Similar to "27 Dresses," Mia's life takes a fairy-tale turn when she discovers she's the heir to the throne of Genovia. As Mia navigates the challenges of royal etiquette and public scrutiny, she also grapples with personal growth and self-acceptance. With the help of her grandmother, Queen Clarisse Renaldi (Julie Andrews), Mia learns to embrace her identity as a princess while staying true to herself amidst the glamorous world of royalty.

CAST

Anne Hathaway

Julie Andrews

Patrick John Flueger

Heather Matarazzo

Hector Elizondo

Mandy Moore

Caroline Goodall

Robert Schwartzman

Erik von Detten

Sean O'Bryan

Directed by Garry Marshall

2 degrees of seperation (similar to The Princess Diaries)

from /25 Delightful Movies Like 'The Princess Diaries'

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16%

37

5.8

In "Made of Honor," commitment-phobic Tom (played by Patrick Dempsey) realizes he's in love with his best friend, Hannah (played by Michelle Monaghan), after she gets engaged. Desperate to win her over, Tom agrees to be her maid of honor, hoping to convince her that he's the one she should marry. As Tom navigates the role of maid of honor, he faces comedic challenges while trying to sabotage Hannah's wedding and confess his true feelings. Similar to "27 Dresses," both films explore themes of unrequited love, friendship, and the complexities of romantic relationships amidst weddings and romantic entanglements.

CAST

Patrick Dempsey

Michelle Monaghan

Kevin McKidd

Kadeem Hardison

Chris Messina

Richmond Arquette

Busy Philipps

Whitney Cummings

Emily Nelson

Kathleen Quinlan

Directed by Paul Weiland

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14%

28

6.4

In "The Ugly Truth," Abby (played by Katherine Heigl), a romantically challenged TV producer, clashes with chauvinistic correspondent Mike (played by Gerard Butler) over their differing views on relationships. When Mike's blunt advice on love becomes a hit segment on Abby's show, they reluctantly team up, leading to comedic confrontations and unexpected romantic tension. Like "27 Dresses," both films feature strong-willed protagonists navigating the ups and downs of romance while confronting their own misconceptions about love and relationships.

CAST

Katherine Heigl

Gerard Butler

Eric Winter

Nick Searcy

Bree Turner

John Michael Higgins

Kevin Connolly

Cheryl Hines

Bonnie Somerville

Jesse D. Goins

Directed by Robert Luketic

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25%

36

6.1

In "What Happens in Vegas," Joy and Jack accidentally get married during a wild night in Las Vegas. When a jackpot win complicates their plans to annul the marriage, the unlikely couple embarks on a series of comedic challenges to outwit each other and claim the money. Despite their initial animosity, Joy and Jack discover unexpected chemistry as they navigate the hilariously chaotic aftermath of their impulsive decision. Similar to "27 Dresses," both films blend romance with comedic hijinks as characters find themselves entangled in unexpected situations that challenge their perceptions of love and commitment.

CAST

Cameron Diaz

Ashton Kutcher

Rob Corddry

Lake Bell

Jason Sudeikis

Treat Williams

Deirdre O'Connell

Michelle Krusiec

Dennis Farina

Zach Galifianakis

Directed by Tom Vaughan

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71%

59

7.1

In "Definitely, Maybe," Will Hayes (Ryan Reynolds) recounts his romantic journey to his curious daughter Maya (Abigail Breslin), concealing the identities of her potential mothers. As he delves into his past relationships with three women, Maya pieces together the puzzle of her mother's identity. This heartwarming romantic comedy explores themes of love, timing, and the complexities of relationships, much like "27 Dresses." Both films feature protagonists reflecting on their romantic histories and searching for meaning in their love lives amidst humorous and heartfelt moments.

CAST

Ryan Reynolds

Abigail Breslin

Elizabeth Banks

Isla Fisher

Rachel Weisz

Kevin Kline

Derek Luke

Liane Balaban

Annie Parisse

Nestor Serrano

Directed by Adam Brooks

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41%

48

6.6

"A Lot Like Love" follows the decade-long relationship between Oliver (Ashton Kutcher) and Emily (Amanda Peet), who meet by chance on a flight and share an instant connection. Despite their different personalities and life paths, they continue to reunite over the years, navigating the ups and downs of love and friendship. Similar to "27 Dresses," this romantic comedy explores the evolving dynamics between two individuals as they navigate the complexities of romance and personal growth, showcasing the enduring power of love amidst life's unpredictable twists and turns.

CAST

Ashton Kutcher

Amanda Peet

Kathryn Hahn

Kal Penn

Ali Larter

Taryn Manning

Aimee Garcia

Jeremy Sisto

Gabriel Mann

Moon Bloodgood

Directed by Nigel Cole

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56%

57

6.5

In "Morning Glory," Becky Fuller (Rachel McAdams) takes on the challenge of revitalizing a struggling morning news show, "Daybreak," by recruiting veteran news anchor Mike Pomeroy and navigating the egos of her co-workers. As she strives to balance her professional ambitions with her personal life, Becky learns valuable lessons about perseverance, teamwork, and the importance of following her passion. Similar to "27 Dresses," this comedy-drama intertwines themes of career dedication and personal fulfillment, highlighting the protagonist's journey of self-discovery and the humorous trials she faces along the

CAST

Rachel McAdams

Harrison Ford

Diane Keaton

Patrick Wilson

Jeff Goldblum

John Pankow

Matt Malloy

J. Elaine Marcos

Ty Burrell

David Fonteno

Directed by Roger Michell

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74%

60

6.5

In "In Her Shoes," two sisters, Rose and Maggie, couldn't be more different. Rose (played by Toni Collette) is a successful lawyer while Maggie (played by Cameron Diaz) is a free-spirited party girl. Despite their contrasting personalities, they share a deep bond. However, their relationship is tested when a revelation about their family's past forces them to confront their differences and reevaluate their sisterhood. Similar to "27 Dresses," which explores themes of sisterhood and familial relationships, "In Her Shoes" delves into the complexities of sisterly love, forgiveness, and self-discovery.

CAST

Cameron Diaz

Toni Collette

Shirley MacLaine

Mark Feuerstein

Ken Howard

Richard Burgi

Brooke Smith

Candice Azzara

Francine Beers

Anson Mount

Directed by Curtis Hanson

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78%

63

7

Set in 1939 London, "Miss Pettigrew Lives for a Day" follows the story of Guinevere Pettigrew, a middle-aged governess who finds herself out of work and desperate for employment. Through a series of fortunate events, she lands a job as the social secretary to a glamorous American actress, Delysia Lafosse. As Miss Pettigrew gets swept into Delysia's whirlwind life of parties, romance, and secrets, she discovers her own inner desires and begins to live life to the fullest. Similar to "27 Dresses," which features a protagonist navigating the world of weddings and romance, "Miss Pettigrew Lives for a Day" explores themes of transformation, seizing opportunities, and embracing life's unexpected adventures.

CAST

Frances McDormand

Amy Adams

Lee Pace

Ciarán Hinds

Shirley Henderson

Mark Strong

Tom Payne

Christina Cole

Clare Clifford

Stephanie Cole

Directed by Bharat Nalluri

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42%

32

6

In "Someone Like You," Jane Goodale (played by Ashley Judd) is a successful talent booker living in New York City who believes she's found "the one" in her charming coworker Ray. However, her world is shattered when Ray abruptly ends their relationship. Seeking solace, Jane develops a theory about men's behavior based on animal instincts, which she shares in a popular magazine column. As she navigates the complexities of love, friendship, and dating, Jane learns valuable lessons about relationships and discovers unexpected connections with her neighbor Eddie. Similar to "27 Dresses," which explores the ups and downs of love and self-discovery, "Someone Like You" delves into the search for Mr. Right amidst life's twists and turns, ultimately finding love where least expected.

CAST

Ashley Judd

Greg Kinnear

Hugh Jackman

Marisa Tomei

Ellen Barkin

Catherine Dent

Laura Regan

Peter Friedman

Mireille Enos

Colleen Camp

Directed by Tony Goldwyn

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6%

14

5.5

"The Accidental Husband" is a romantic comedy that follows the life of Dr. Emma Lloyd (Uma Thurman), a popular radio talk show host in New York City who gives relationship advice to her listeners. However, her own love life takes an unexpected turn when she discovers she is accidentally married to Patrick Sullivan (Jeffrey Dean Morgan), a charming but down-to-earth firefighter. As Emma tries to rectify the situation and annul the marriage, she finds herself drawn to Patrick's genuine nature and begins to question her own romantic beliefs. Similar to "27 Dresses," the film explores themes of love, mistaken identity, and the unexpected twists and turns of relationships.

CAST

Uma Thurman

Colin Firth

Jeffrey Dean Morgan

Sam Shepard

Isabella Rossellini

Brooke Adams

Keir Dullea

Justina Machado

Lindsay Sloane

Ajay Naidu

Directed by Griffin Dunne