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Movies Like How I Married My High School Crush

If you liked How I Married My High School Crush (2007), a comedy and family movie directed by David Winkler, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

  1. 1Disenchanted

    Disenchanted (2022)

    ★ 6.6/10Also comedy and family

    Disillusioned with life in the city, feeling out of place in suburbia, and frustrated that her happily ever after hasn’t been so easy to find, Giselle turns to the magic of Andalasia for help. Accidentally transforming…

  2. 2The Wizards Return: Alex vs. Alex

    The Wizards Return: Alex vs. Alex (2013)

    ★ 7.8/10Also family and comedy

    While trying to prove to her family she can be mature and responsible, teen wizard Alex Russo conjures up a spell to rid herself of her bad qualities, unintentionally creating a Good and Evil Alex. When Evil Alex gets…

  3. 3Stuck in the Suburbs

    Stuck in the Suburbs (2004)

    ★ 6/10Also family and comedy

    Brittany Aarons is one of the many girls who has a crush on popular singer and boy-toy Jordan Cahill. However, she is bored of living a suburban existence and seeks a little something more.

  4. 4Sofia the First: Once Upon a Princess

    Sofia the First: Once Upon a Princess (2012)

    ★ 7.4/10Also family and fantasy

    Set in the storybook world of Enchancia, the music-filled movie follows Sofia, an average girl whose life suddenly changes when her mother marries the king and she is whisked off to live in a castle with her mom, new…

  5. 5In Your Dreams

    In Your Dreams (2025)

    ★ 6.9/10Also comedy and family

    Stevie and her little brother Elliot journey into the wildly absurd landscape of their own dreams to ask the Sandman to grant them the perfect family.

  6. 6Mulan II

    Mulan II (2004)

    ★ 6.5/10Also comedy and family

    Fa Mulan gets the surprise of her young life when her love, Captain Li Shang asks for her hand in marriage. Before the two can have their happily ever after, the Emperor assigns them a secret mission, to escort three…

  7. 7iParty with Victorious

    iParty with Victorious (2011)

    ★ 7.3/10Also comedy and family

    Carly discovers her boyfriend Steven Carson has been cheating on her with Tori Vega, so the gang flies out to Los Angeles where they meet Tori and the gang from Hollywood Arts. They attend a party hosted by Kenan…

  8. 8Teen Beach 2

    Teen Beach 2 (2015)

    ★ 6.8/10Also tv movie and family

    When characters from the movie musical “Wet Side Story” get stuck in the real world, teens Brady and Mack must find a way to return them home.

  9. 9Snoopy Presents: Welcome Home, Franklin

    Snoopy Presents: Welcome Home, Franklin (2024)

    ★ 7.7/10Also family and comedy

    Franklin is new to town and hoping to make friends, but his usual tactics don't work on the Peanuts gang. When the Soap Box Derby arrives, he's sure it's a chance to impress new pals and teams up with the only other…

  10. 10Mickey and Minnie Wish Upon a Christmas

    Mickey and Minnie Wish Upon a Christmas (2021)

    ★ 7/10Also tv movie and comedy

    After a series of mishaps, Mickey, Minnie and the gang are separated all over the world and must try to get back to Hot Dog Hills by Christmas Eve. A mysterious and jolly stranger shows up to tell them about The…

  11. 11I Yabba-Dabba Do!

    I Yabba-Dabba Do! (1993)

    ★ 6.5/10Also tv movie and comedy

    A grown-up Pebbles and Bamm-Bamm decide to get married.

  12. 12Gnome Alone

    Gnome Alone (2017)

    ★ 6.1/10Also fantasy and family

    When Chloe discovers that her new home's garden gnomes are not what they seem, she must decide between the pursuit of a desired high school life and taking up the fight against the Troggs.

  13. 13Scooby-Doo! The Mystery Begins

    Scooby-Doo! The Mystery Begins (2009)

    ★ 6.4/10Also comedy and fantasy

    Unjustly accused of staging a spooky practical joke complete with ghosts, Daphne, Velma, Fred and Shaggy are suspended from Coolsville High. To clear their names, they team up to solve the supernatural mystery…and head…

  14. 14The Loud House Movie

    The Loud House Movie (2021)

    ★ 7.2/10Also family and comedy

    The Loud family travel to Scotland and discover they are descendants of Scottish royalty as they move into their giant ancestral castle.

  15. 15Merry Christmas, Drake & Josh

    Merry Christmas, Drake & Josh (2008)

    ★ 7.3/10Also comedy and family

    Step brothers Drake and Josh must give a foster family the best Christmas ever or face years in jail for a Christmas party gone wrong.

  16. 16Ron's Gone Wrong

    Ron's Gone Wrong (2021)

    ★ 7.8/10Also family and comedy

    In a world where walking, talking, digitally connected bots have become children's best friends, an 11-year-old finds that his robot buddy doesn't quite work the same as the others do.

  17. 17Beverly Hills Chihuahua 2

    Beverly Hills Chihuahua 2 (2011)

    ★ 5.9/10Also comedy and family

    Puppy mayhem turns the lives of newlywed Chihuahua parents Papi and Chloe upside down when their rambunctious, mischievous puppies present one challenge after another. But when their human owners end up in trouble, the…

  18. 18Pooh's Heffalump Movie

    Pooh's Heffalump Movie (2005)

    ★ 6.9/10Also family and comedy

    Who or what exactly is a Heffalump? The lovable residents of the Hundred Acre Wood -- Winnie the Pooh, Rabbit, Tigger, Eeyore, Kanga and the rest of the pack -- embark on a journey of discovery in search of the elusive…

  19. 193 Men and a Little Lady

    3 Men and a Little Lady (1990)

    ★ 5.8/10Also family and comedy

    Sylvia's work increasingly takes her away from the three men who help bring up Mary, her daughter. When she decides to move to England and take Mary with her, the three men are heartbroken at losing the two most…

  20. 20Slumberland

    Slumberland (2022)

    ★ 7.2/10Also comedy and family

    A young girl discovers a secret map to the dreamworld of Slumberland, and with the help of an eccentric outlaw, she traverses dreams and flees nightmares, with the hope that she will be able to see her late father again.

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