15 Best Romantic Comedies Similar to The Wedding Planner

Nearly 25 years after its initial release, The Wedding Planner continues to resonate with fans seeking movies that embody the enchanting spirit of romantic comedies. Starring Jennifer Lopez as Mary Fiore, a top wedding planner who excels at crafting elaborate ceremonies yet struggles in her personal love life, the film unfolds a captivating narrative when she meets Steve (Matthew McConaughey) – the very groom of one of her upcoming weddings.

Despite receiving mixed reviews from critics, The Wedding Planner became a commercial success, amassing almost $100 million globally (according to Box Office Mojo).The undeniable chemistry between Lopez and McConaughey significantly contributed to their stardom in the rom-com genre. As audiences still indulge in this beloved classic, numerous other films featuring similar romantic and comedic elements, particularly set against wedding backdrops, are sure to captivate fans.

15 Sweet Home Alabama (2002)

Directed By Andy Tennant

Venturing into common rom-com territory, Sweet Home Alabama showcases a familiar love triangle. Reese Witherspoon shines as Melanie Carmichael, a city professional engaged to Andrew (Patrick Dempsey), who finds herself compelled to return to Alabama to divorce her estranged husband, Jake (Josh Lucas).Much like Mary and Steve in The Wedding Planner, Melanie navigates tension with Jake, revealing their deeper emotional connection despite the conflicts.

14 Wedding Crashers (2005)

Directed By David Dobkin

Set against the backdrop of weddings, Wedding Crashers introduces audiences to two lawyers, played by Vince Vaughn and Owen Wilson, who infiltrate weddings for free food and drinks while pursuing romantic escapades. However, things take a turn when Wilson’s character falls for the bride’s sister, disrupting their longstanding wedding-crashing rules. While this film leans more into comedy than romance, it still provides engaging romantic subplots that echo the heart of The Wedding Planner.

13 America’s Sweethearts (2001)

Directed By Joe Roth

America’s Sweethearts features the charming Kiki, played by Julia Roberts, as a sister and assistant thrust into the chaos surrounding her movie star sister, Gwen Harrison (Catherine Zeta-Jones).As Gwen reconnects with her ex, Kiki secretly grapples with her feelings for him, reflecting Mary’s plight in The Wedding Planner. Both characters juggle their own desires within challenging relational dynamics.

12 Moonstruck (1987)

Directed By Norman Jewison

In Moonstruck, Cher portrays Loretta, who agrees to marry her steady but dull boyfriend, only to find herself romantically entwined with his dynamic brother Ronny (Nicolas Cage).This film showcases the shift from animosity to romance, paralleling Mary and Steve’s contentious relationship prior to their inevitable attraction in The Wedding Planner.

11 Clueless (1995)

Directed By Amy Heckerling

A modern adaptation of Jane Austen’s Emma, Clueless stars Alicia Silverstone as Cher, a high school matchmaker who realizes her own romantic shortcomings while helping others. Both Cher and Mary share an affinity for orchestrating love stories, while their personal adventures remind viewers of the complexities of distilling true happiness amidst the chaos of relationships.

10 What Women Want (2000)

Directed By Nancy Meyers

In a rare male-led romantic comedy, What Women Want features Mel Gibson as Nick, a man granted the ability to hear women’s thoughts. As he navigates his newfound insight, a parallel emerges as both Nick and Mary confront their personal conflicts amidst professional considerations, creating a relatable authenticity that resonates across audiences.

9 The Wedding Date (2005)

Directed By Clare Kilner

The Wedding Date chronicles Kat (Debra Messing), who hires an escort (Dermot Mulroney) to accompany her to her sister’s wedding, mirroring the lengths both Kat and Mary go to navigate their romantic insecurities. The film highlights how wedding scenarios amplify personal dilemmas, allowing for humor and heartfelt moments alike.

8 Just Married (2003)

Directed By Shawn Levy

Following the ups and downs of newlyweds Tom (Ashton Kutcher) and Sarah (Brittany Murphy) during their ill-fated honeymoon, Just Married adopts a different narrative structure by starting at the wedding, exploring the pitfalls of romance afterwards. Like Mary in The Wedding Planner, Sarah faces external pressures while trying to cultivate a meaningful relationship.

7 27 Dresses (2008)

Directed By Anne Fletcher

27 Dresses introduces Jane (Katherine Heigl), a serial bridesmaid who watches her dreams of love remain unfulfilled. Like Mary, Jane navigates the complexity of being surrounded by weddings, while simultaneously realizing that true connection may be right in front of her, adding a layer of depth to their romantic journeys.

6 Because I Said So (2007)

As Michael Lehmann

Focusing on a proactive mother’s quest for her daughter’s happiness, Because I Said So sees Diane Keaton as a protective parent who seeks to secure a suitable partner for her daughter Milly (Mandy Moore).The film reflects the familial pressures depicted in The Wedding Planner, highlighting the sometimes overwhelming desires behind finding love.

5 The Sweetest Thing (2002)

Directed By Roger Kumble

In a feel-good tale featuring strong female camaraderie, The Sweetest Thing follows Christina (Cameron Diaz) as she unexpectedly finds herself entwined with a man on the cusp of marrying someone else. Both Christina and Mary experience the heartache of true love thwarted by impending weddings, bringing depth to their search for happiness.

4 My Big Fat Greek Wedding (2002)

Directed By Joel Zwick

My Big Fat Greek Wedding features Toula (Nia Vardalos), a woman balancing cultural expectations with her desire for romance, ultimately discovering love in an unexpected partner. Similarly, The Wedding Planner highlights the chaos surrounding weddings and families, underlining how love can blossom even amidst tradition.

3 Monster-In-Law (2005)

Directed By Robert Luketic

In Monster-In-Law, Jennifer Lopez plays Charlie, whose new romance is marred by the overbearing nature of her future mother-in-law (Jane Fonda).Just as Mary navigates familial expectations in The Wedding Planner, Charlie’s journey emphasizes the challenges of blending new love with family dynamics.

2 My Best Friend’s Wedding (1997)

Directed By PJ Hogan

In My Best Friend’s Wedding, Julia Roberts portrays Jules, who attempts to sabotage her best friend’s wedding upon realizing her true feelings. The love triangle dynamic mirrors that of The Wedding Planner, illustrating the complexity of relationships and the emotional turmoil that weddings can evoke.

1 How To Lose A Guy In 10 Days (2003)

Directed By Donald Petrie

In How to Lose a Guy in 10 Days, Kate Hudson stars as Andie, a writer attempting to win and then lose a man in ten days as part of an article. Matthew McConaughey’s character Benjamin provides a contrasting portrayal of romance compared to his role as Steve in The Wedding Planner. Their mutual games reveal the complexities of romantic pursuits, culminating in unexpected chemistry.

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