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100+ Movies like 27 Dresses

3.2
2008 Comedy, Romance

Discover movies similar to the romantic comedy "27 Dresses," where Jane, a perpetual bridesmaid, falls for the cynical wedding writer Kevin while planning her sister's wedding to her boss, whom she secretly loves. Explore films revolving around love triangles, sibling rivalries, and the complexities of relationships, often with a humorous twist. Find stories of women navigating the challenges of unrequited love, family dynamics, and finding their true path to happiness, frequently set against the backdrop of weddings and the bridesmaid experience.

Before You Say 'I Do'

Before You Say 'I Do'

3.0
2009

Both "27 Dresses" and "Before You Say 'I Do'" revolve around a woman who is unlucky in love and a man who tries to win her heart. In "27 Dresses", Jane is a perpetual bridesmaid who has an unrequited crush on her boss George, while in "Before You Say 'I Do'", Jane is jaded after being cheated on by her ex-husband Doug. The male leads, Kevin and George, respectively, take unconventional steps to pursue the women they love. Kevin writes an exposé on Jane's bridesmaid life, while George travels back in time to prevent Jane from marrying Doug. Both movies feature a sister character (Tess in "27 Dresses") who initially comes between the lead couple. Ultimately, the movies culminate in the lead characters, Jane and Kevin/George, ending up together after overcoming obstacles and misunderstandings.

Daughter of the Bride

Daughter of the Bride

3.1
2023

Both "27 Dresses" and "Daughter of the Bride" revolve around a central female character who is heavily involved in wedding planning and bridesmaid duties for others, while struggling with her own romantic relationships and finding a partner. The protagonists, Jane in "27 Dresses" and Kate in "Daughter of the Bride", are single women who have been bridesmaids numerous times but have yet to find their own happily-ever-after. They develop romantic interests (Kevin and Josh, respectively) who initially clash with their wedding-centric lifestyles. There are also subplots involving the protagonists' relationships with their sisters/mothers getting married, leading to conflicts and revelations about their own desires for love and marriage. Both films culminate in the protagonists finding love and having their own weddings, where they are surrounded by the brides they previously served as bridesmaids.

The Wedding Planner

The Wedding Planner

3.0
2001

Both "27 Dresses" and "The Wedding Planner" revolve around a female protagonist who is obsessed with weddings and planning them, but struggles to find her own true love. The main characters, Jane and Mary, are constantly involved in planning weddings for others while harboring unrequited feelings for a man who ends up engaged to someone else. They meet a cynical man, Kevin and Steve respectively, who initially clashes with their romantic ideals but eventually becomes their love interest. The plots follow the protagonists as they navigate the complexities of their feelings, betrayals, and misunderstandings before ultimately finding love with the cynical man and having their own dream wedding with all the bridesmaids they had helped over the years. The movies explore similar themes of self-discovery, the pursuit of true love, and the importance of honesty in relationships.

Love, Weddings & Other Disasters

Love, Weddings & Other Disasters

3.0
2020

Both "27 Dresses" and "Love, Weddings & Other Disasters" revolve around the central theme of weddings and the chaos surrounding them. The protagonists, Jane in "27 Dresses" and Jessie in "Love, Weddings & Other Disasters", find themselves deeply involved in wedding planning and coordination, often against their will or in unexpected circumstances. The movies explore the complexities of relationships, with the main characters navigating romantic entanglements and unrequited love. Jane has an unrequited crush on her boss George, while Jessie develops feelings for Mack amidst the wedding chaos. Both films feature love triangles and misunderstandings that drive the plot forward. Wedding planning serves as a backdrop for character growth and self-discovery. Jane learns to assert herself and pursue her own happiness, while Jessie embraces her newfound role as a wedding planner despite initial setbacks. The movies also touch on themes of sisterhood, family dynamics, and the pursuit of one's dreams. Ultimately, both films culminate in the protagonists finding love and happiness, often in unexpected ways, while navigating the complexities of wedding planning and relationships.

Bride Wars

Bride Wars

3.1
2009

Both "27 Dresses" and "Bride Wars" revolve around female best friends whose close relationship is strained by their upcoming weddings. The protagonists, Jane in "27 Dresses" and Emma and Liv in "Bride Wars", have been bridesmaids numerous times but struggle to find their own happiness in marriage. A central conflict arises when the friends' weddings are accidentally scheduled for the same day, pitting them against each other in a rivalry filled with sabotage and betrayal. However, their lifelong bond ultimately triumphs over the wedding chaos, allowing them to reconcile and find fulfillment in their romantic relationships and friendship. The movies explore themes of female friendship, the pressures of wedding planning, and finding one's identity beyond being a bridesmaid.

Degrassi Takes Manhattan

Degrassi Takes Manhattan

5.0
2010

Both "27 Dresses" and "Degrassi Takes Manhattan" revolve around a central female character who is unlucky in love and relationships. Jane from "27 Dresses" has been a bridesmaid 27 times but never the bride, while Jane from "Degrassi" is cheated on by her boyfriend Spinner. The movies follow their journeys of self-discovery, moving on from past heartbreaks, and finding new love interests - Kevin for Jane in "27 Dresses" and the band member George for Jane in "Degrassi". A key similarity is the love triangle dynamic, with Jane's sister Tess stealing her crush George in "27 Dresses", mirroring Holly J.'s feud with Fiona over Declan in "Degrassi". Both movies culminate in weddings where the protagonists realize their true feelings and find closure, with Jane ending up with Kevin and Spinner marrying Emma.

Bridget Jones's Diary

Bridget Jones's Diary

3.4
2001

Both "27 Dresses" and "Bridget Jones's Diary" follow the romantic journey of an unlucky-in-love woman who is infatuated with the wrong man. The protagonists, Jane and Bridget, are single women who serve as bridesmaids/assistants to their friends' weddings while harboring unrequited feelings for their respective bosses. They meet cynical men, Kevin and Mark, who initially dislike them but eventually become love interests. The movies explore themes of self-discovery, overcoming insecurities, and finding true love. The plots revolve around misunderstandings, betrayals, and the protagonists' realization that their initial romantic interests were misguided. Ultimately, Jane and Bridget end up with the men who truly appreciate them for who they are, Kevin and Mark, after a series of comedic mishaps and emotional growth.

I Do (But I Don't)

I Do (But I Don't)

2.9
2004

Both "27 Dresses" and "I Do (But I Don't)" revolve around female protagonists who are wedding planners/bridesmaids and have a passion for weddings. The main characters, Jane and Lauren, find themselves involved in planning weddings for brides who are portrayed as "bridezillas" - demanding and controlling. A key similarity is the romantic subplot where Jane and Lauren develop feelings for men who are engaged to the bridezillas they are working for. The movies explore themes of unrequited love, betrayal, and the protagonists' struggles to find their own happiness amidst their dedication to others' weddings. The climax in both films involves the protagonists confronting the bridezillas and exposing their lies, leading to the weddings being called off. Ultimately, the endings see the protagonists finding love themselves and having their own dream weddings with the men they fell for.

Beauty & the Briefcase

Beauty & the Briefcase

3.0
2010

Both "27 Dresses" and "Beauty & the Briefcase" follow a similar romantic comedy plot structure where the female protagonist initially has misguided priorities and an unrealistic checklist for her ideal partner. In "27 Dresses", Jane is obsessed with being a bridesmaid and has an unrequited crush on her boss, while in "Beauty & the Briefcase", Lane is fixated on finding a corporate man who meets her extensive checklist of attributes. Through a series of events, both women are deceived and betrayed by men they become involved with (Kevin and Liam, respectively), leading them to re-evaluate their priorities. Ultimately, they realize their true feelings for another man closer to them (Kevin for Jane, Tom for Lane) who better aligns with their authentic selves. The movies parallel each other in the character arcs of the protagonists finding self-discovery and true love by overcoming their superficial checklists and embracing more meaningful connections.

It Had to Be You

It Had to Be You

3.1
2000

Both "27 Dresses" and "It Had to Be You" follow a similar romantic comedy plot where the main characters, Jane and Charlie, develop feelings for someone they initially disliked or found unappealing (Kevin and Anna). The stories involve love triangles with the protagonists' love interests being engaged to someone else (Jane's crush on her boss George, Charlie's fiancée Claire, Anna's fiancé David). The protagonists bond over their shared experiences in wedding planning and preparations. There are subplots involving the protagonists' friends (Henry and Tracey) who also develop a romantic connection. The climax involves the protagonists sabotaging or revealing the truth about the fiancés' flaws, leading to the breakup of those relationships. In the end, the protagonists end up together after realizing their true feelings, with their previous love interests hoping for a second chance. The movies also share themes of finding true love, overcoming initial judgments, and the complexities of modern relationships and weddings.

I Give It a Year

I Give It a Year

2.8
2013

Both "27 Dresses" and "I Give It a Year" are romantic comedy films that explore the challenges and complications of relationships and marriage. The central plot revolves around a couple who initially fall in love and get married, but soon face difficulties and temptations that test their commitment. In both movies, one partner develops feelings for someone else, leading to infidelity or near-infidelity. The films also feature a close friend or confidant who serves as a romantic interest for one of the main characters. The stories follow the couples as they navigate the ups and downs of their first year of marriage, with humorous and relatable situations highlighting the realities of married life. Ultimately, the movies explore themes of love, loyalty, and finding the right partner through a comedic lens.

Sex and the City

Sex and the City

3.3
2008

Both "27 Dresses" and "Sex and the City" revolve around the themes of love, relationships, and weddings. The main characters, Jane in "27 Dresses" and Carrie in "Sex and the City", struggle with commitment issues and have complicated relationships with the men in their lives. A central plot point in both movies involves the main character being betrayed or let down by their partner regarding marriage plans - Jane is betrayed by Kevin publishing an article about her, while Carrie is left at the altar by Mr. Big. The movies also explore the dynamics of female friendships, with the main characters relying on their close friends for support. Ultimately, both Jane and Carrie find happiness and get married to their respective partners in the end, after overcoming various obstacles and self-doubts about marriage.

The Sweetest Thing

The Sweetest Thing

2.8
2002

Both "27 Dresses" and "The Sweetest Thing" revolve around single women in their late 20s who are unlucky in love and have commitment issues. The protagonists, Jane and Christina, are surrounded by friends getting married while they remain single bridesmaids. A key plot point in both films is the protagonists developing feelings for men they initially dislike - Jane for the cynical Kevin, and Christina for the seemingly taken Peter. Misunderstandings and betrayals involving these love interests lead to major conflicts. The films explore themes of female friendship, finding one's identity beyond romantic relationships, and overcoming fears of commitment. Ultimately, the protagonists find love and get married themselves, with their friends in supporting roles.

I Me Wed

I Me Wed

2.6
2007

Both "27 Dresses" and "I Me Wed" revolve around single women who are obsessed with weddings and face societal pressure to get married. The protagonists, Jane and Isabel, are constantly nagged by their friends and family about finding a husband. In an act of defiance, they decide to marry themselves, planning elaborate wedding ceremonies. However, their plans are complicated when they unexpectedly meet potential love interests, Kevin and Colin, respectively. The movies explore the themes of self-love, societal expectations, and finding true romance. Both Jane and Isabel ultimately realize their true feelings for their romantic partners and end up marrying them instead of themselves, overcoming their initial resistance to traditional marriage.

Made of Honor

Made of Honor

3.2
2008

Both "27 Dresses" and "Made of Honor" are romantic comedy films that follow a similar plot structure. The main characters, Jane in "27 Dresses" and Tom in "Made of Honor", are best friends with the female lead who becomes engaged to someone else. Jane has an unrequited crush on her boss George, while Tom realizes his romantic feelings for his best friend Hannah after she gets engaged to a wealthy Scotsman. The films explore the friends' attempts to sabotage or stop the weddings in hopes of winning over the woman they love. Key plot points include the main characters serving as bridesmaids/maid of honor, dealing with jealous ex-girlfriends, and ultimately confessing their love and ending up with the bride at the climax. The movies share common themes of friendship, unrequited love, and the challenges of speaking up about one's true feelings.

Chaos Theory

Chaos Theory

3.1
2007

Both "27 Dresses" and "Chaos Theory" revolve around romantic relationships and the complexities of love and commitment. The central characters face challenges and misunderstandings within their relationships, leading to temporary separations and the need to reevaluate their feelings and priorities. In "27 Dresses", Jane's unrequited love for her boss George and her sister Tess's deception in pursuing George create tension and conflict. Similarly, in "Chaos Theory", Frank's misunderstanding about the paternity of Susan's child and Buddy's revelation about being Jesse's father strain Frank and Susan's marriage. Both movies explore themes of trust, honesty, and the importance of communication in relationships. The characters must navigate through misunderstandings, betrayals, and revelations before ultimately reconciling and finding happiness with their true loves. The plots follow a similar structure, with the main characters initially facing obstacles and complications in their romantic relationships, leading to temporary breakups or separations. However, through self-reflection and realizations about their true feelings, they ultimately reunite with their partners by the end of the movies.

Last Chance Harvey

Last Chance Harvey

3.1
2008

Both "27 Dresses" and "Last Chance Harvey" are romantic comedy films that follow a similar narrative arc. The protagonists, Jane and Harvey, are both attending family weddings where they feel like outsiders and disconnected from their loved ones. They unexpectedly meet and form a connection with another person, Kevin and Kate respectively, who initially seems incompatible but with whom they gradually develop a romantic relationship. The films explore themes of finding love and self-discovery, as Jane and Harvey learn to prioritize their own happiness over pleasing others. The climax involves a dramatic event at a wedding where the protagonists assert themselves, leading to a resolution where they end up together with their new romantic partners after overcoming personal obstacles.

What's Your Number?

What's Your Number?

3.3
2011

Both "27 Dresses" and "What's Your Number?" revolve around a single woman in her late 20s/early 30s who is unlucky in love and has been a bridesmaid many times. The protagonists, Jane and Ally, are fixated on finding "the one" and settling down, but struggle with commitment issues and making poor romantic choices. A key plot point in both films involves the woman meeting a cynical man (Kevin and Colin) who initially clashes with her views on love and marriage. However, as they spend more time together, romantic feelings develop between the two. The films explore themes of self-discovery, letting go of the past, and learning to embrace one's true self to find happiness. Both stories culminate in the woman realizing her feelings for the cynical man and choosing him over a more conventional romantic prospect.

Confetti

Confetti

2.8
2006

Both "27 Dresses" and "Confetti" revolve around the theme of weddings and the challenges couples face in planning their nuptials. The central plot of "Confetti" involves a competition to hold the most original wedding, mirroring Jane's role as a bridesmaid in 27 weddings in "27 Dresses". Both films follow multiple couples as they navigate the stresses and obstacles of wedding planning, from family tensions to personal insecurities. The movies explore the dynamics between the couples, their relationships with wedding planners/coordinators, and the pressure to create the perfect wedding day. Ultimately, the stories culminate in the weddings themselves, where the couples overcome their issues and find happiness in marriage, similar to Jane's journey to her own wedding at the end of "27 Dresses".

The New Romantic

The New Romantic

3.1
2018

Both "The New Romantic" and "27 Dresses" follow a young woman navigating the complexities of relationships and finding her true self. In "27 Dresses", Jane is a perpetual bridesmaid who falls for her boss while helping her sister plan her wedding, mirroring Blake's journey in "The New Romantic" as a student journalist exploring the world of sugar dating. Both protagonists experience betrayal - Jane by her sister and Kevin, Blake by Ian - which forces them to re-evaluate their priorities. Ultimately, they find fulfillment and love by embracing their authentic selves, with Jane ending up with Kevin and Blake with her friend Jacob. The movies parallel each other in their exploration of sisterhood, self-discovery, and the search for genuine connection amidst societal pressures and expectations.