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19 Movies Like Definitely, Maybe to Watch Next

If you’re a fan of romantic comedies like Definitely, Maybe, you’re in for a treat! This genre, known for its heartwarming stories and charming characters, has plenty of films that capture the same magic. Here are 19 movies that will make you laugh, cry, and fall in love all over again.

1. Love, Actually

Love, Actually is a delightful ensemble film that intertwines multiple love stories during the holiday season. Featuring a star-studded cast including Hugh Grant, Emma Thompson, and Keira Knightley, this movie explores the complexities of love in its many forms.

2. Notting Hill

In Notting Hill, a simple bookstore owner, played by Hugh Grant, unexpectedly falls for a famous actress, portrayed by Julia Roberts. This charming film captures the essence of an unlikely romance blossoming in the heart of London.

3. 13 Going on 30

13 Going on 30 tells the story of Jenna Rink, played by Jennifer Garner, who magically transforms from a 13-year-old girl to a 30-year-old woman overnight. The film is a delightful mix of comedy and romance, with Mark Ruffalo co-starring as her childhood best friend.

4. The Proposal

In The Proposal, Sandra Bullock stars as a high-powered executive who convinces her assistant, played by Ryan Reynolds, to marry her to avoid deportation. The film is filled with hilarious moments and unexpected romance.

5. Crazy, Stupid, Love

Crazy, Stupid, Love follows the journey of a recently divorced man, played by Steve Carell, who gets a makeover from a suave young man, portrayed by Ryan Gosling. The film also stars Julianne Moore and Emma Stone, adding depth to this heartwarming story.

6. The Holiday

The Holiday features two women, played by Cameron Diaz and Kate Winslet, who swap homes for the holiday season to escape their romantic troubles. In doing so, they each find unexpected love, with Jude Law and Jack Black co-starring.

7. Friends with Benefits

Friends with Benefits stars Justin Timberlake and Mila Kunis as two friends who decide to add physical intimacy to their relationship without emotional attachment. The film humorously explores the complications that arise when feelings start to develop.

8. When Harry Met Sally

When Harry Met Sally is a classic romantic comedy that questions whether men and women can ever truly be just friends. Starring Billy Crystal and Meg Ryan, this film is known for its witty dialogue and memorable scenes.

9. 500 Days of Summer

500 Days of Summer is a non-linear romantic comedy that explores the rise and fall of a relationship between Tom, played by Joseph Gordon-Levitt, and Summer, portrayed by Zooey Deschanel. The film offers a realistic look at love and heartbreak.

10. How to Lose a Guy in 10 Days

In How to Lose a Guy in 10 Days, Kate Hudson plays a journalist who tries to drive away a man, played by Matthew McConaughey, as part of an article. Little does she know, he has his own agenda to make her fall in love with him.

11. About Time

About Time is a touching romantic comedy about a young man, played by Domhnall Gleeson, who discovers he can travel through time. He uses this ability to win the heart of Mary, portrayed by Rachel McAdams, and to create the perfect life.

12. The Vow

The Vow stars Channing Tatum and Rachel McAdams as a married couple whose lives are turned upside down after a car accident erases the wife’s memory. The film is a poignant exploration of love and commitment.

13. P.S. I Love You

In P.S. I Love You, Hilary Swank plays a widow who discovers letters left by her late husband, Gerard Butler, designed to help her move on and find happiness. This emotional film beautifully portrays love and loss.

14. Just Go with It

Just Go with It features Adam Sandler as a plastic surgeon who convinces his assistant, played by Jennifer Aniston, to pose as his soon-to-be-divorced wife to cover up a lie. The film is packed with comedic situations and unexpected romance.

15. The Notebook

The Notebook is a timeless love story based on Nicholas Sparks’ novel, starring Ryan Gosling and Rachel McAdams. The film chronicles the enduring love between a young couple from different social backgrounds.

16. Bridget Jones’s Diary

Bridget Jones’s Diary follows the life of a single woman, played by Renée Zellweger, as she navigates the ups and downs of her love life. Colin Firth and Hugh Grant co-star in this hilarious and relatable romantic comedy.

17. Silver Linings Playbook

Silver Linings Playbook stars Bradley Cooper as a man struggling with bipolar disorder who forms an unexpected bond with a young widow, played by Jennifer Lawrence. The film is a heartwarming tale of love and recovery.

18. La La Land

La La Land is a modern musical that tells the story of an aspiring actress, played by Emma Stone, and a jazz musician, portrayed by Ryan Gosling. Their love story is set against the backdrop of a vibrant and dreamy Los Angeles.

19. To All the Boys I’ve Loved Before

To All the Boys I’ve Loved Before follows Lara Jean, played by Lana Condor, whose secret love letters are accidentally sent out to her crushes. The film is a charming and heartfelt exploration of teenage romance.