If you’re a fan of the charming 2008 rom-com 27 Dresses starring Katherine Heigl and James Marsden, you’ll definitely want to check out these other delightful movies that share similar themes of love, weddings, and finding your own happily ever after. From classic favorites to more recent releases, these 22 films are sure to make you laugh, swoon, and believe in the magic of romance all over again. So grab some popcorn, snuggle up on the couch, and get ready to fall in love with these must-watch movies like 27 Dresses!
1. The Proposal (2009)
The Proposal pairs Sandra Bullock and Ryan Reynolds in this hilarious and heartwarming tale of an ambitious book editor who convinces her assistant to marry her to avoid deportation. As they travel to his hometown in Alaska to meet his quirky family, real feelings begin to develop between them. With plenty of laugh-out-loud moments and undeniable chemistry between the leads, The Proposal is a delightful rom-com that’s perfect for fans of 27 Dresses.
2. Bridesmaids (2011)
While Bridesmaids is a raunchier and more outrageous comedy compared to the sweet nature of 27 Dresses, it still revolves around the craziness of wedding festivities and the complexities of female friendship. Kristen Wiig stars as Annie, a down-on-her-luck maid of honor trying to navigate the expensive and exhausting duties of being in her best friend’s wedding. With an incredible ensemble cast that includes Maya Rudolph, Rose Byrne, and Melissa McCarthy in her breakout role, Bridesmaids is a gut-bustingly funny and surprisingly poignant look at modern relationships.
3. The Ugly Truth (2009)
Katherine Heigl reunited with her 27 Dresses director Anne Fletcher for another rom-com, this time opposite Gerard Butler. In The Ugly Truth, Heigl plays a romantically challenged morning show producer who reluctantly takes dating advice from the chauvinistic correspondent (Butler) to win the affections of her handsome doctor neighbor. While the battle-of-the-sexes premise is a bit cliché, the movie still offers plenty of funny and charming moments thanks to the appealing leads.
4. Life As We Know It (2010)
Like 27 Dresses, Life as We Know It finds Katherine Heigl playing a perpetually single woman who suddenly finds herself in close quarters with an unexpected suitor. After their mutual best friends die in an accident, Holly (Heigl) and Messer (Josh Duhamel) must put aside their differences to raise their orphaned goddaughter. The “opposites attract” setup may be predictable, but Heigl and Duhamel’s winning chemistry and the film’s touching moments make it a sweet, enjoyable watch.
5. The Big Wedding (2013)
The Big Wedding boasts an all-star ensemble cast including Robert De Niro, Diane Keaton, Susan Sarandon, Katherine Heigl, Amanda Seyfried, and Topher Grace. The comedy follows a long-divorced couple who must pretend to still be married for their adopted son’s wedding weekend to appease his religious biological mother. While it received mixed reviews, The Big Wedding still provides some genuine laughs and a fun look at family dysfunction amidst a joyous occasion.
6. Jenny’s Wedding (2015)
Katherine Heigl takes on more serious subject matter in this indie drama about a woman who finally decides to come out to her conservative family and marry her longtime girlfriend. Jenny’s Wedding thoughtfully explores the challenges that still face many LGBTQ+ couples and the importance of living your truth. It’s a touching, intimate portrait anchored by strong performances from Heigl and Alexis Bledel as her fiancée.
7. Empire Records (1995)
For a nostalgic ’90s pick, look no further than the cult classic Empire Records. Set over the course of one eventful day, the movie follows the eclectic group of employees at an independent record store as they cope with the news that the shop might be sold to a big chain. While not strictly a rom-com, Empire Records does feature a sweet “will they or won’t they” subplot between characters played by Liv Tyler and Rory Cochrane. But the real draw is the memorable ensemble and quotable one-liners that make this a endlessly re-watchable comfort movie.
8. Serendipity (2001)
The charming fantasy romance Serendipity asks the question of whether fate and destiny play a role in matters of the heart. After a magical evening together, Jonathan (John Cusack) and Sara (Kate Beckinsale) part ways and leave their future up to chance, only to spend the next few years wondering about what might have been. With the sparkling chemistry between Cusack and Beckinsale and a fun supporting turn from Eugene Levy, Serendipity is a wistful, enchanting film about the serendipitous nature of love.
9. The Princess Diaries (2001)
Anne Hathaway became a star with her leading role in this modern fairy tale, playing awkward American teenager Mia who learns that she is actually heir to the throne of a small European country. Under the tutelage of her regal grandmother (Julie Andrews), Mia undergoes a glamorous makeover while navigating the perils of high school and princess lessons. Sweet, funny, and full of heart, The Princess Diaries is a contemporary spin on the classic Cinderella story that still holds up today.
10. Notting Hill (1999)
Notting Hill is one of the defining rom-coms of the ’90s, pairing Julia Roberts and Hugh Grant at the height of their stardom. She plays a famous American actress who falls for a charming British bookshop owner, but their budding romance is complicated by her celebrity lifestyle. With a sharp script full of memorable lines and a strong supporting cast, Notting Hill is a witty, sophisticated comedy about fame and finding love when you least expect it.
11. Easy A (2010)
This smart, funny teen movie served as a breakout vehicle for Emma Stone, playing a clean-cut high school student who uses rumors of her (fictional) promiscuity to climb the social ladder. Inspired by Nathaniel Hawthorne’s The Scarlet Letter, Easy A offers a fresh, modern take on slut-shaming and the power of gossip in the digital age. Stone shines in the lead role, showcasing the comedic chops and charisma that would make her a movie star.
12. My Best Friend’s Wedding (1997)
My Best Friend’s Wedding shares some key similarities with 27 Dresses – both center around a woman secretly in love with an engaged friend. Julia Roberts stars as Julianne, a food critic who realizes she’s in love with her longtime best friend Michael (Dermot Mulroney) and schemes to stop his wedding to the sweet, wealthy Kimmy (Cameron Diaz). While Julianne is not always the most likable heroine, Roberts’ effervescent charm keeps you rooting for her. The movie also features a scene-stealing Rupert Everett as Julianne’s gay confidante, and a truly iconic singalong to “I Say a Little Prayer.”
13. The Wedding Planner (2001)
Jennifer Lopez stars as Mary, a successful and ambitious wedding planner who meets her match in Steve (Matthew McConaughey), a charming doctor who sweeps her off her feet. The only problem? Mary is planning his wedding to another woman. With a sweet and sassy performance from Lopez and a dreamy McConaughey at his rom-com best, The Wedding Planner is a fun, feel-good flick about the crazy things we do for love.
14. The Wedding Date (2005)
Debra Messing plays Kat, a single New Yorker who hires suave male escort Nick (Dermot Mulroney) to pose as her boyfriend at her sister’s wedding in England. Predictably, real sparks fly between them amidst the wedding hijinks. While the premise is a bit silly, Messing and Mulroney have enough chemistry and charm to sell it. The Wedding Date is a cute, breezy rom-com perfect for a girls’ night in.
15. The Wedding Singer (1998)
The Wedding Singer is a sweet and hilarious ode to the ’80s starring Adam Sandler as Robbie, the titular crooner, and Drew Barrymore as Julia, the waitress he falls for. The only snag in their budding romance? Julia is engaged to a smarmy womanizer. With a killer retro soundtrack, colorful costumes, and Sandler and Barrymore at their most adorable, The Wedding Singer is a beloved rom-com for a reason.
16. Bride Wars (2009)
Kate Hudson and Anne Hathaway play lifelong best friends who have always dreamed of getting married at New York’s Plaza Hotel in June. But when a clerical error causes their weddings to be booked on the same day, the two brides turn into bridezillas as they try to outdo and sabotage each other. While the pranks get a bit mean-spirited at times, Bride Wars is still a funny and frothy look at female friendship and wedding madness.
17. The Five-Year Engagement (2012)
The Five-Year Engagement follows the prolonged journey to the altar of Tom (Jason Segel) and Violet (Emily Blunt), whose wedding keeps getting delayed by various circumstances. Co-written by Segel, the movie has a slightly more bittersweet and realistic tone than most fluffy rom-coms, with a focus on the actual struggles of long-term commitment. But it’s still very funny and romantic, with an excellent supporting cast including Chris Pratt and Alison Brie.
18. Mamma Mia! (2008)
The smash hit adaptation of the ABBA jukebox musical, Mamma Mia! is the definition of a feel-good movie. Meryl Streep plays Donna, a former pop star preparing for her daughter Sophie’s (Amanda Seyfried) wedding at her Greek island hotel. But Sophie has secretly invited three of Donna’s old flames (Pierce Brosnan, Colin Firth, and Stellan Skarsgard), believing one of them to be her father. With infectious energy, gorgeous scenery, and wall-to-wall ABBA tunes, Mamma Mia! is pure cinematic sunshine.
19. Crazy Rich Asians (2018)
While not strictly wedding-themed, the opulent engagement party in Crazy Rich Asians could give any cinematic nuptials a run for their money. Constance Wu stars as Rachel, an American professor who travels to Singapore to meet her boyfriend Nick’s (Henry Golding) family, only to discover they are one of the wealthiest dynasties in Asia. Dazzling, funny, and swooningly romantic, Crazy Rich Asians is a watershed moment for representation that still delivers all the delights of a classic rom-com.
20. Runaway Bride (1999)
Runaway Bride reunites Pretty Woman stars Julia Roberts and Richard Gere for another swoon-worthy romance. Roberts plays small-town hardware store owner Maggie, who has left multiple fiancés at the altar, earning her the tabloid nickname “The Runaway Bride.” Gere is Ike, the cynical big-city journalist who comes to town to cover her upcoming fourth wedding attempt. Sparks predictably fly between them as Ike tries to get to the bottom of Maggie’s cold feet. It may not reinvent the wheel, but Runaway Bride coasts on the star power and chemistry of its legendary leads.
21. The Wedding Crashers (2005)
This raunchy comedy follows two divorce mediators (Owen Wilson and Vince Vaughn) who spend their weekends crashing weddings to meet women. But when one of them falls for a bridesmaid (Rachel McAdams) at the biggest wedding of the year, they get in over their heads. With rapid-fire jokes and an up-for-anything cast, Wedding Crashers is a raucous good time that still manages to sneak in some genuine heart.
22. Love, Wedding, Repeat (2020)
For a clever twist on the wedding rom-com, check out this British charmer set at an Italian destination wedding. The hook is that it shows the same day multiple times with slight variations that lead to vastly different outcomes, all hinging on who sits at which table. With a large ensemble navigating various entanglements and an irreverent sense of humor, Love, Wedding, Repeat is a fresh, fun take on wedding shenanigans.
Whether you’re in the mood for big laughs, swoon-worthy romance, or just a feel-good story, these 22 films are perfect for any fan of 27 Dresses. From awkward encounters to grand gestures of love, crazy wedding antics to heartfelt confessions, these movies capture all the ups and downs of dating and relationships. They’ll make you laugh, cry, and believe in happily ever after.
So next time you’re in need of a good rom-com, queue up one of these delightful picks and let yourself get swept away in the romance of it all. Whether it’s a cozy night in or a fun movie marathon with friends, these films are guaranteed to leave you feeling the love. And who knows – maybe your own Prince (or Princess) Charming is just a meet-cute away!
