Movies like Never Been Kissed (1999)
The best movies like Never Been Kissed (1999) are 10 Things I Hate About You (1999), Drive Me Crazy (1999) and Clueless (1995). If Never Been Kissed hooked you with its romance and comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedLove Untangled (2025)8.2/10 from 243 votes
- NewestHow to Lose a Popularity Contest (2026)Released 2026
10 Things I Hate About You (1999)
After discovering his high school crush can't date until her brash older sister does, a lovesick teen enlists a bad-boy classmate to woo her.
Why it matches: Fans watch both · both comedy & romance
Worth the HypeMovies like thisDrive Me Crazy (1999)
Nicole and Chase live next door to each other but are worlds apart. However, they plot a scheme to date each other in order to attract the interest and jealousy of their respective romantic prey. But in the mist of planning a gala centennial celebration, Nicole and Chase find that the one they always wanted was closer than they ever thought.
Why it matches: Fans watch both · both romance & comedy
Popcorn FlickMovies like thisClueless (1995)
Shallow, rich and socially successful Cher is at the top of her Beverly Hills high school's pecking scale. Seeing herself as a matchmaker, Cher first coaxes two teachers into dating each other. Emboldened by her success, she decides to give hopelessly klutzy new student Tai a makeover. When Tai becomes more popular than she is, Cher realizes that her disapproving ex-stepbrother was right about how misguided she was -- and falls for him.
Why it matches: Fans watch both · both comedy & romance
Worth the HypeMovies like thisShe's All That (1999)
High school hotshot Zach Siler is the envy of his peers. But his popularity declines sharply when his cheerleader girlfriend, Taylor, leaves him for sleazy reality-television star Brock Hudson. Desperate to revive his fading reputation, Siler agrees to a seemingly impossible challenge. He has six weeks to gain the trust of nerdy outcast Laney Boggs -- and help her to become the school's next prom queen.
Why it matches: Fans watch both · both comedy & romance
Popcorn FlickMovies like thisGet Over It (2001)
When Berke Landers, a popular high school basketball star, gets dumped by his life-long girlfriend, Allison, he soon begins to lose it. But with the help of his best friend Felix's sister Kelly, he follows his ex into the school's spring musical. Thus ensues a love triangle loosely based upon Shakespeare's "A Midsummer Night's Dream", where Berke is only to find himself getting over Allison and beginning to fall for Kelly.
Why it matches: Fans watch both · both comedy & romance
SnoozefestMovies like thisSay Anything... (1989)
Average student and eternal optimist Lloyd Dobler seeks to capture the heart of Diane Court, a beautiful but unattainable valedictorian classmate. He surprises just about everyone - including himself - when she returns the sentiment. However, Diane's divorced, over-protective father soon begins to disapprove of the match, and Lloyd realises that it's going to take more than just the power of love to conquer all.
Why it matches: Fans watch both · both romance & comedy
Worth the HypeMovies like thisFirst Daughter (2004)
Samantha MacKenzie, the daughter of the president of the United States, arrives at college with a group of Secret Service agents. Samantha, however, resents their presence and decides she wants to attend school just like a normal student.
Why it matches: Fans watch both · both comedy & drama
Popcorn FlickMovies like thisTrippin' (1999)
Greg is near the end of his senior year in high school, wanting to go to the prom, eyeing Cinny (the school's beauty with brains) from afar, and regularly trippin', daydreaming about being a big success as a poet, a student, a lover. His mom wants him to apply to colleges, but Greg hasn't a clue. One of his teachers, Mr. Shapic, tries to inspire him, too. He finally figures out he can get close to Cinny if he asks her for help with college applications. But friendship isn't enough, he wants romance and a prom date. So, he tells a few lies and, for awhile, it seems to be working. Then, things fall apart and Greg has to figure out how to put the trippin aside and get real.
Why it matches: Fans watch both · both comedy & romance
Sixteen Candles (1984)
With the occasion all but overshadowed by her sister's upcoming wedding, angst-ridden Samantha faces her 16th birthday with typical adolescent dread. Samantha pines for studly older boy Jake, but worries that her chastity will be a turnoff for the popular senior. Meanwhile, she must constantly rebuff the affections of nerdy Ted, who is unfortunately the only boy in school who seems to take an interest in her.
Why it matches: Fans watch both · both comedy
Popcorn FlickMovies like thisHead Over Heels (2001)
Ordinary single girl Amanda Pierce unexpectedly finds herself sharing an awesome Manhattan apartment with four sexy supermodels. Determined to bring Amanda into their world, the models give her the ultimate makeover. The plan works fabulously as Amanda connects with next door charmer Jim Winston. That is, until one night while spying on him, Amanda thinks she sees the man of her dreams committing a cold blooded crime.
Why it matches: Fans watch both · both romance & comedy
SnoozefestMovies like thisLove Untangled (2025)
A lovestruck teen plans to win the school heartthrob by going from curly to straight hair — until a new transfer student changes everything.
Why it matches: Fans watch both · both romance & drama
Absolute CinemaMovies like thisThe DUFF (2015)
Bianca's universe turns upside down when she learns that her high school refers to her as a ‘DUFF' (Designated Ugly Fat Friend). Hoping to erase that label, she enlists the help of a charming jock and her favorite teacher. Together they'll face the school's mean girl and remind everyone that we are all someone's DUFF… and that's totally fine.
Why it matches: Fans watch both · both romance & comedy
Popcorn FlickMovies like thisChasing Liberty (2004)
The President's daughter, unable to experience life like a normal 18 year-old, escapes from her entourage of Secret Service agents while traveling in Europe. She falls in love with a handsome British stranger, who also happens to be working undercover for her father.
Why it matches: Fans watch both · both comedy & romance
Popcorn FlickMovies like thisJust One of the Guys (1985)
When Terry Griffith loses her high school's writing competition, she's convinced that it's because she's a girl. So Terry decides to change high schools and pose as a boy to prove her point. Her brother, Buddy, helps her pass as a guy so well that she is soon making friends with the boys at school, including the attractive Rick, who becomes her new best friend. But her gender-swapping makes things difficult when she falls in love with him.
Why it matches: Fans watch both · both comedy & romance
Popcorn FlickMovies like thisHow to Lose a Popularity Contest (2026)
A rebellious student and a perfectionist overachiever form an unlikely alliance in their race for student body president, discovering unexpected feelings along the way.
Why it matches: Fans watch both · both romance & comedy
She's the Man (2006)
Viola Hastings is in a real jam. Complications threaten her scheme to pose as her twin brother, Sebastian, and take his place at a new boarding school. She falls in love with her handsome roommate, Duke, who loves beautiful Olivia, who has fallen for Sebastian! As if that were not enough, Viola's twin returns from London ahead of schedule but has no idea that his sister has already replaced him on campus.
Why it matches: Fans watch both · both comedy & romance
Popcorn FlickMovies like thisEasy A (2010)
Olive, an average high school student, sees her below-the-radar existence turn around overnight once she decides to use the school's gossip grapevine to advance her social standing. Now her classmates are turning against her and the school board is becoming concerned, including her favorite teacher and the distracted guidance counselor. With the support of her hilariously idiosyncratic parents and a little help from a long-time crush, Olive attempts to take on her notorious new identity and crush the rumor mill once and for all.
Why it matches: Fans watch both · both comedy
Popcorn FlickMovies like thisWhatever It Takes (2000)
A nerdy teen, Ryan Woodman is smitten with the popular and gorgeous Ashley Grant, who apparently has no interest in him. Meanwhile, dim star athlete Chris Campbell has his eye on Ryan's brainy and beautiful friend, Maggie Carter. The two agree to help each other in their romantic quests, but, as they come closer to their goals, both Ryan and Chris suspect that they might be pursuing the wrong girls.
Why it matches: Fans watch both · both drama & comedy
SnoozefestMovies like thisPretty in Pink (1986)
Andie is an outcast, hanging out either with her older boss, who owns the record store where she works, or her quirky high school classmate Duckie, who has a crush on her. When one of the rich and popular kids at school, Blane, asks Andie out, it seems too good to be true. As Andie starts falling for Blane, she begins to realize that dating someone from a different social sphere is not easy.
Why it matches: Fans watch both · both romance & drama
Popcorn FlickMovies like thisCan't Buy Me Love (1987)
Nerdy high schooler Ronald Miller rescues cheerleader Cindy Mancini from parental punishment after she accidentally destroys her mother's designer clothes. Ronald agrees to pay for the $1,000 outfit on one condition: that she will act as though they're a couple for an entire month. As the days pass, however, Cindy grows fond of Ronald, making him popular. But when Ronald's former best friend gets left behind, he realizes that social success isn't everything.
Why it matches: Fans watch both · both comedy & romance
Popcorn FlickMovies like this50 First Dates (2004)
Henry is a player skilled at seducing women. But when this veterinarian meets Lucy, a girl with a quirky problem when it comes to total recall, he realizes it's possible to fall in love all over again…and again, and again. That's because the delightful Lucy has no short-term memory, so Henry must woo her day after day until he finally sweeps her off her feet.
Why it matches: Fans watch both · both comedy & romance
Popcorn FlickMovies like thisThe Other Zoey (2023)
Highly intelligent computer major Zoey Miller is uninterested in romantic love, but her life is turned upside down when Zack, the school's soccer star, gets amnesia and mistakes Zoey for his girlfriend.
Why it matches: Fans watch both · both romance & drama
Popcorn FlickMovies like thisWhen Harry Met Sally... (1989)
Sex always gets in the way of friendships between men and women. At least, that's what Harry Burns believes. So when Harry meets Sally Albright and a deep friendship blossoms between them, Harry's determined not to let his attraction to Sally destroy it. But when a night of weakness ends in a morning of panic, can the pair avoid succumbing to Harry's fears by remaining friends and admitting they just might be the perfect match for each other?
Why it matches: Fans watch both · both comedy & romance
Worth the HypeMovies like thisHow to Deal (2003)
For teenager Halley, love seems like an alien concept. Her mother is divorcing her father, who is dating a younger woman Halley can't stand. Her sister is about to get married and doesn't realize that her fiancé is not the man of her dreams. And her best friend has fallen madly in love for the first time, leaving Halley to feel even more alone. But, when she meets edgy Macon, she learns what love is really all about.
Why it matches: Fans watch both · both drama & comedy
SnoozefestMovies like thisCan't Hardly Wait (1998)
It's graduation day at Huntington Hills High, and you know what that means - time to party. And not just any party, either. This one will be a night to remember, as the nerds become studs, the jocks are humiliated, and freshman crushes blossom into grown-up romance.
Why it matches: Fans watch both · both comedy & romance
Popcorn FlickMovies like thisMean Girls (2004)
Cady Heron is a hit with The Plastics, the A-list girl clique at her new school, until she makes the mistake of falling for Aaron Samuels, the ex-boyfriend of alpha Plastic Regina George.
Why it matches: Fans watch both · both drama & comedy
Worth the HypeMovies like thisTrojan War (1997)
Brad is about to hook up with the girl of his dreams, but runs into a problem, no condom. So Brad sets out into the night to find one, running into many obstacles along the way, while not knowing his best friend, Leah is in love with him.
Why it matches: Fans watch both · both comedy & romance
Popcorn FlickMovies like thisNo Hard Feelings (2023)
On the brink of losing her childhood home, Maddie discovers an intriguing job listing: wealthy helicopter parents looking for someone to “date” their introverted 19-year-old son, Percy, before he leaves for college. To her surprise, Maddie soon discovers the awkward Percy is no sure thing.
Why it matches: Fans watch both · both comedy & romance
Popcorn FlickMovies like thisJust My Luck (2006)
Manhattanite Ashley is known to many as the luckiest woman around. After a chance encounter with a down-and-out young man, however, she realizes that she's swapped her fortune for his.
Why it matches: Fans watch both · both comedy & romance
Popcorn FlickMovies like thisRomy and Michele's High School Reunion (1997)
Two not-too-bright party girls reinvent themselves for their high school reunion. Armed with a borrowed Jaguar, new clothes and the story of their success as the inventors of Post-It notes, Romy and Michele descend on their alma mater, but their façade crumbles quickly.
Why it matches: Fans watch both · both comedy
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Frequently asked questions
What are the best movies like Never Been Kissed?
The closest matches to Never Been Kissed are 10 Things I Hate About You (1999), Drive Me Crazy (1999) and Clueless (1995). Below are 27 more, each with the reason it matches.
What should I watch after Never Been Kissed?
People who watched Never Been Kissed most often go on to 10 Things I Hate About You (1999), Drive Me Crazy (1999) and Clueless (1995).
What is the highest-rated movie like Never Been Kissed?
Love Untangled (2025), rated 8.2/10 by 243 TMDB users.
What is the newest movie like Never Been Kissed?
How to Lose a Popularity Contest (2026) is the most recent release on this list.
Are there English movies like Never Been Kissed?
Yes: 10 Things I Hate About You (1999), Drive Me Crazy (1999) and Clueless (1995).
How are movies similar to Never Been Kissed chosen?
First come films that Trakt’s viewers watch alongside Never Been Kissed, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.