If you’re a fan of the classic 1990 romantic comedy Pretty Woman, starring Julia Roberts and Richard Gere, you’re in for a treat. We’ve compiled a list of 15 charming, witty, and heartwarming movies that capture a similar vibe – modern fairytales with unlikely love stories, charismatic leads, and plenty of romance and laughs. Get ready to swoon, giggle, and fall in love with these must-watch films for any rom-com aficionado.
1. Notting Hill (1999)
Notting Hill is a charming British romantic comedy that shares many similarities with Pretty Woman. Both films feature an unlikely romance between two people from different worlds. In this case, it’s a famous American actress (played by Julia Roberts) who falls for a humble London bookshop owner (Hugh Grant).
The film beautifully captures the challenges and joys of their blossoming relationship as they navigate the complexities of fame and ordinary life. With its witty dialogue, lovable characters, and iconic scenes (like Roberts’ character telling off snooty diners), Notting Hill is a must-watch for any fan of Pretty Woman.
2. The Proposal (2009)
The Proposal is a hilarious and heartwarming rom-com that features a fake relationship turned real, much like the arrangement in Pretty Woman. Sandra Bullock stars as a high-powered book editor who faces deportation to Canada. To stay in the U.S., she convinces her assistant (Ryan Reynolds) to marry her.
As they travel to his hometown in Alaska to announce their engagement, they unexpectedly start to develop real feelings for each other. With laugh-out-loud moments, sizzling chemistry between the leads, and a touching story about finding love in unexpected places, The Proposal is a delightful film that captures the magic of Pretty Woman.
3. Maid in Manhattan (2002)
Maid in Manhattan is a modern Cinderella story that echoes the rags-to-riches theme of Pretty Woman. Jennifer Lopez stars as Marisa Ventura, a single mother working as a maid in a posh Manhattan hotel. When a wealthy politician (Ralph Fiennes) mistakes her for a guest, a whirlwind romance ensues.
Like Pretty Woman, the film explores themes of class differences and the transformative power of love. With its charming leads, lush New York setting, and feel-good story, Maid in Manhattan is a delightful romantic comedy that will leave you feeling uplifted.
4. My Best Friend’s Wedding (1997)
My Best Friend’s Wedding is another Julia Roberts classic that shares some similarities with Pretty Woman. In this film, Roberts plays Julianne, a food critic who realizes she’s in love with her best friend Michael (Dermot Mulroney) just as he’s about to marry someone else.
Like Vivian in Pretty Woman, Julianne undergoes a transformation as she confronts her feelings and learns important lessons about love and friendship. With its stellar cast (including Cameron Diaz), memorable musical moments, and exploration of complex relationships, My Best Friend’s Wedding is a must-see for fans of Pretty Woman.
5. Two Weeks Notice (2002)
Two Weeks Notice is a charming romantic comedy that features a love story between two people from different worlds, similar to Pretty Woman. Sandra Bullock stars as Lucy, a dedicated lawyer who becomes the chief counsel for George (Hugh Grant), a wealthy real estate developer.
As they work together and butt heads, they start to develop unexpected feelings for each other. The film explores themes of career aspirations, personal integrity, and the power of love to change people. With its witty banter, strong female lead, and undeniable chemistry between Bullock and Grant, Two Weeks Notice is a delightful film that captures the spirit of Pretty Woman.
6. The Holiday (2006)
The Holiday is a charming romantic comedy that features two parallel love stories, both of which echo the themes of unexpected romance and personal growth found in Pretty Woman. The film follows two women, Amanda (Cameron Diaz) and Iris (Kate Winslet), who swap homes for the holidays to escape their relationship troubles.
In their new locations, they each meet a local man (Jude Law and Jack Black) and sparks fly. As they navigate these new romances, both women learn valuable lessons about love, self-worth, and taking chances. With its all-star cast, picturesque settings, and heartwarming story, The Holiday is a perfect film to watch if you loved Pretty Woman.
7. Runaway Bride (1999)
Runaway Bride reunites Pretty Woman‘s dynamic duo, Julia Roberts and Richard Gere, in another delightful romantic comedy. Roberts plays Maggie, a woman known for leaving multiple men at the altar. Gere is Ike, a journalist assigned to write a story about her.
As Ike investigates Maggie’s past and gets to know her, they develop a complicated relationship that mirrors the push-and-pull dynamic of Vivian and Edward in Pretty Woman. With its charming small-town setting, exploration of commitment fears, and undeniable chemistry between the leads, Runaway Bride is a must-watch for fans of Pretty Woman.
8. While You Were Sleeping (1995)
While You Were Sleeping is a sweet and funny romantic comedy that shares some similarities with Pretty Woman‘s Cinderella story. Sandra Bullock stars as Lucy, a lonely transit worker who saves a handsome commuter (Peter Gallagher) from an oncoming train.
When he falls into a coma, a misunderstanding leads his family to believe Lucy is his fiancée. As she gets to know them, she starts to fall for his charming brother (Bill Pullman). Like Pretty Woman, the film features a working-class heroine, a case of mistaken identity, and a heartwarming love story. With its cozy winter setting, lovable characters, and touching moments, While You Were Sleeping is a delightful film that captures the magic of falling in love unexpectedly.
9. Breakfast at Tiffany’s (1961)
Breakfast at Tiffany’s is a classic romantic comedy that paved the way for films like Pretty Woman. Audrey Hepburn stars as Holly Golightly, a charming New York socialite with a mysterious past. When a struggling writer (George Peppard) moves into her building, they develop a complicated friendship that blossoms into something more.
Like Vivian in Pretty Woman, Holly is a complex character with hidden depths and a yearning for love and acceptance. With its iconic fashion, memorable moments (like Hepburn’s rendition of “Moon River”), and exploration of identity and belonging, Breakfast at Tiffany’s is a timeless film that shares some themes with Pretty Woman.
10. Sabrina (1954)
Sabrina is a classic romantic comedy that features a Cinderella-like transformation, similar to Pretty Woman. Audrey Hepburn stars as Sabrina, the daughter of a wealthy family’s chauffeur. After returning from Paris as a sophisticated young woman, she catches the eye of the family’s playboy son (William Holden) and his serious older brother (Humphrey Bogart).
As Sabrina navigates the complexities of love and social class, she undergoes a personal transformation that mirrors Vivian’s journey in Pretty Woman. With its witty dialogue, lush settings, and charming performances, Sabrina is a delightful film that paved the way for modern romantic comedies like Pretty Woman.
11. Never Been Kissed (1999)
Never Been Kissed is a sweet and funny romantic comedy that features a transformative journey for its heroine, similar to Pretty Woman. Drew Barrymore stars as Josie, a nerdy copy editor who goes undercover as a high school student for a story.
As she navigates the challenges of teenage life and falls for her English teacher (Michael Vartan), Josie learns valuable lessons about self-acceptance and taking risks. Like Vivian in Pretty Woman, Josie undergoes a physical and emotional transformation that leads her to find love and happiness. With its nostalgic setting, charming performances, and feel-good story, Never Been Kissed is a delightful film that shares some themes with Pretty Woman.
12. She’s All That (1999)
She’s All That is a classic teen romantic comedy that features a makeover story similar to Pretty Woman. Freddie Prinze Jr. stars as Zack, a popular high school jock who bets he can turn any girl into the prom queen. He sets his sights on Laney (Rachael Leigh Cook), a nerdy art student.
As Zack helps Laney transform her appearance and gain confidence, they start to develop real feelings for each other. Like Pretty Woman, the film explores themes of social status, self-worth, and the power of love to change people. With its memorable moments (like the iconic prom entrance), charming leads, and feel-good story, She’s All That is a fun and romantic film that echoes some elements of Pretty Woman.
13. The Wedding Date (2005)
The Wedding Date is a charming romantic comedy that features a fake relationship turned real, similar to the arrangement in Pretty Woman. Debra Messing stars as Kat, a single woman who hires a male escort (Dermot Mulroney) to pose as her boyfriend for her sister’s wedding.
As they pretend to be a couple, they start to develop genuine feelings for each other. Like Pretty Woman, the film explores themes of love, trust, and the blurring of lines between fantasy and reality. With its witty dialogue, likable characters, and romantic moments, The Wedding Date is a delightful film that captures some of the magic of Pretty Woman.
14. 27 Dresses (2008)
27 Dresses is a fun and heartwarming romantic comedy that features a heroine who undergoes a personal transformation, similar to Vivian in Pretty Woman. Katherine Heigl stars as Jane, a perpetual bridesmaid who’s secretly in love with her boss (Edward Burns). When her younger sister (Malin Akerman) starts dating him, Jane’s world is turned upside down.
As she navigates the challenges of being a bridesmaid, dealing with her feelings, and finding her own happiness, Jane learns valuable lessons about love, self-worth, and going after what she wants. With its charming leads, relatable moments, and exploration of the complexities of relationships, 27 Dresses is a delightful film that shares some themes with Pretty Woman.
15. 10 Things I Hate About You (1999)
10 Things I Hate About You is a clever and charming teen romantic comedy loosely based on Shakespeare’s “The Taming of the Shrew.” Like Pretty Woman, it features an unlikely romance between two people from different worlds.
Julia Stiles stars as Kat, a smart and independent high school student who doesn’t believe in love. Heath Ledger plays Patrick, a mysterious bad boy hired to date Kat so her popular younger sister can start dating. As they spend time together, Kat and Patrick start to develop real feelings for each other.
With its witty dialogue, memorable characters (like the lovable nerd Cameron), and exploration of themes like trust, identity, and the power of love, 10 Things I Hate About You is a delightful film that captures the spirit of Pretty Woman for a younger generation.
These 15 movies all share elements that made Pretty Woman such a beloved classic, from charming leads and unlikely romances to transformative journeys and explorations of love across social divides. Whether you’re in the mood for a classic rom-com, a modern fairy tale, or a nostalgic teen flick, these films are sure to delight fans of Pretty Woman.
So next time you’re in the mood for a romantic movie night, give one of these delightful films a watch. You might just find your new favorite feel-good love story. And if you’re looking for the perfect romantic gift to go with your movie night, consider surprising your loved one with a beautiful bouquet of red roses – a classic symbol of love and romance, just like Pretty Woman.
