If you love Never Been Kissed (1999), a heartwarming romantic comedy about an undercover journalist who navigates the ups and downs of high school while trying to find love, you’re not alone. Drew Barrymore’s quirky and lovable character has made this film a classic among fans of feel-good rom-coms. Whether you’re looking for stories that focus on second chances, self-discovery, or the challenges of teenage romance, there are plenty of films out there that mirror the themes and spirit of Never Been Kissed. For those who appreciate its lighthearted humor mixed with deeper emotional moments, we’ve compiled a list of movies like Never Been Kissed that offer similar charm, humor, and heartfelt moments. And for those who enjoy movies that evoke a blend of action and emotion, you’ll also find suggestions for movies like Man on Fire, where love and redemption play a central role.
1. 10 Things I Hate About You (1999)
One of the most beloved teen rom-coms of the ’90s, 10 Things I Hate About You is a modern take on Shakespeare’s The Taming of the Shrew. Starring Heath Ledger and Julia Stiles, this film revolves around a high school love story with a sharp sense of humor and an abundance of charm. Much like Never Been Kissed, it blends awkward moments of self-discovery with romantic tension. The witty dialogue, endearing characters, and unforgettable soundtrack make 10 Things I Hate About You a perfect pick for anyone who enjoyed movies like Never Been Kissed.
2. She’s All That (1999)
In this rom-com classic, Freddie Prinze Jr. and Rachel Leigh Cook star in a high school transformation story. She’s All That tells the tale of Zack, a popular high school jock who takes on the challenge of turning a shy, awkward girl into the prom queen. Like Never Been Kissed, the film explores themes of self-esteem, transformation, and the importance of being true to oneself. The chemistry between the leads and the charming narrative make this a standout movie for fans of movies like Never Been Kissed.
3. The Princess Diaries (2001)
This Disney classic follows the story of Mia Thermopolis (Anne Hathaway), an awkward teenager who discovers she’s heir to the throne of a small European country. As Mia navigates her newfound royal life, she also learns important life lessons about self-worth and love. The Princess Diaries shares the theme of self-discovery and personal growth that Never Been Kissed embodies. If you’re a fan of feel-good, coming-of-age movies that also bring a touch of romance and humor, this is a must-watch for anyone who loves movies like Never Been Kissed.
4. Clueless (1995)
Clueless, starring Alicia Silverstone, is a witty and stylish adaptation of Jane Austen’s Emma. The film follows Cher Horowitz, a popular and well-meaning high school student who sets out to play matchmaker for her friends and ultimately learns a lot about herself. Much like Never Been Kissed, Clueless is filled with humor, romance, and self-reflection. The movie’s perfect blend of teen drama, comedy, and romance has made it a lasting favorite for fans of movies like Never Been Kissed.
5. To All the Boys I’ve Loved Before (2018)
This Netflix original takes a modern spin on the classic teen rom-com formula, following Lara Jean Covey, whose secret love letters are accidentally sent out to her crushes. Much like Never Been Kissed, the film blends awkward situations with tender moments of love, making it a charming and relatable story about growing up and finding romance. To All the Boys I’ve Loved Before is perfect for fans of movies like Never Been Kissed, offering both humor and heartfelt romance.
6. Love, Simon (2018)
Love, Simon tells the story of Simon Spier, a high school senior who has not come out to his friends and family yet. As he navigates his romantic feelings for a fellow student, Simon’s journey towards self-acceptance becomes both funny and emotional. This film has a similar feel to Never Been Kissed, as it explores themes of identity, love, and personal growth in a way that’s both heartfelt and entertaining. If you enjoy movies like Never Been Kissed, Love, Simon will strike the right chord with its charm and relatable storyline.
7. Notting Hill (1999)
This romantic comedy starring Julia Roberts and Hugh Grant tells the story of an ordinary man who falls in love with a famous actress. Notting Hill shares the theme of unlikely love that Never Been Kissed so beautifully portrays, but it takes a more mature approach to romance. The movie’s witty script, memorable characters, and heartfelt moments make it a classic. Fans of movies like Never Been Kissed will appreciate its emotional depth and feel-good atmosphere.
8. The Proposal (2009)
Starring Sandra Bullock and Ryan Reynolds, The Proposal follows the story of a high-powered book editor who convinces her assistant to marry her so she can avoid deportation. What starts as a business arrangement turns into something more, much like the evolving love story in Never Been Kissed. The comedic elements, along with the romance and charm, make The Proposal a great option for fans of movies like Never Been Kissed.
9. Miss Congeniality (2000)
Miss Congeniality, starring Sandra Bullock, is a fun and heartfelt movie about an FBI agent who goes undercover at a beauty pageant. Bullock’s performance as the unlikely beauty queen makes this a feel-good, entertaining watch. Like Never Been Kissed, it features a character who undergoes a transformation—both in terms of outward appearance and inner growth. The movie blends humor, romance, and personal development, making it perfect for fans of movies like Never Been Kissed.
10. Pretty Woman (1990)
Pretty Woman is a romantic comedy that tells the story of a wealthy businessman who falls in love with a prostitute, played by Julia Roberts. The film explores themes of self-worth and transformation, much like Never Been Kissed. Pretty Woman is beloved for its blend of humor, romance, and a little bit of fairy-tale magic. If you enjoyed the themes of self-discovery and love in movies like Never Been Kissed, Pretty Woman will captivate you with its charm.
11. Legally Blonde (2001)
In Legally Blonde, Reese Witherspoon plays Elle Woods, a sorority girl who enrolls at Harvard Law School in a bid to win back her ex-boyfriend, only to discover her true potential. Like Never Been Kissed, Legally Blonde features a lovable, underestimated protagonist who experiences personal growth and a surprising romance. Fans of movies like Never Been Kissed will enjoy Elle’s quirky journey of self-discovery and empowerment.
12. The Ugly Truth (2009)
This romantic comedy, starring Katherine Heigl and Gerard Butler, is about a TV producer and a chauvinistic columnist who work together to make a show about relationships. The Ugly Truth shares the theme of love and self-discovery in a comedic setting, much like Never Been Kissed. The chemistry between the leads and the humor will appeal to fans of movies like Never Been Kissed.
13. While You Were Sleeping (1995)
While You Were Sleeping tells the story of a lonely transit worker (Sandra Bullock) who saves a man’s life and ends up being mistaken for his fiancée while he is in a coma. Like Never Been Kissed, it’s a film about unlikely love, self-discovery, and the importance of being true to oneself. The heartwarming romance and the charming humor make it a perfect fit for those who enjoy movies like Never Been Kissed.
14. 27 Dresses (2008)
This rom-com stars Katherine Heigl as a woman who has been a bridesmaid 27 times but has never been the bride. 27 Dresses features themes of love, self-worth, and the desire for recognition in a fun and lighthearted way, much like Never Been Kissed. Fans of movies like Never Been Kissed will love the charming storyline and the character’s journey to finding true love.
15. The Wedding Planner (2001)
Starring Jennifer Lopez and Matthew McConaughey, The Wedding Planner is about a wedding planner who falls in love with the groom of one of her clients. This romantic comedy blends humor with heartfelt romance and a little bit of chaos, much like Never Been Kissed. If you enjoy movies like Never Been Kissed, The Wedding Planner will charm you with its endearing characters and sweet storyline.
These movies like Never Been Kissed offer a perfect blend of humor, romance, and self-discovery. Whether you’re looking for quirky high school comedies or more mature romantic tales, there’s something on this list for everyone. For fans of love stories with a twist, the films will resonate with their heartwarming narratives and memorable characters. Just like Man on Fire combines action with heart, these movies offer a mix of both romance and the emotional depth you’re craving.
