Movies Like My High Schooler Is My Wingman
If you liked My High Schooler Is My Wingman (2026), a comedy and romance movie directed by Aurelia Day, 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
Sex Appeal (2022)
★ 6.6/10Also comedy and romanceAvery, a teenager with a tendency towards perfectionism, enlists her friend Larson to help her prepare for her first time with her long-distance boyfriend.
- 2
¿Quieres ser mi hijo? (2023)
★ 8.4/10Also comedy and romanceLu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.
- 3
Desperados (2020)
★ 6/10Also comedy and romanceA panicked young woman and her two best friends fly to Mexico to delete a ranting email she sent to her new boyfriend. On arrival, they run into her former beau, who soon gets caught up in their frantic scheme.
- 4
Players (2024)
★ 6.1/10Also romance and comedyNew York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it takes to go from simply scoring to playing…
- 5
Puppy Love (2023)
★ 7/10Also comedy and romanceAfter a disastrous first date, wild-child Nicole and socially-anxious Max vow to lose each other’s numbers until they learn that their dogs found a love match, and now puppies are on the way! The hilariously mismatched…
- 6
The Long Weekend (2005)
★ 5.8/10Also comedy and romanceCooper is an actor who sees life as one big party, while Ed is in advertising and takes life too seriously. When Ed gets stressed over a deadline he has to meet, his brother Cooper works hard in trying to get his…
- 7
A Nice Girl Like You (2020)
★ 5.8/10Also comedy and romanceLucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her on a whirlwind and surprising journey…
- 8
Girl on a Bicycle (2013)
★ 5.9/10Also comedy and romancePaolo, an Italian tour bus driver living in Paris, has just summoned up the courage to propose marriage to his German girlfriend Greta. However, a chance encounter with a French woman on a bicycle the very next day…
- 9
My Sassy Girl (2008)
★ 6.8/10Also comedy and romanceA guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
- 10
Zack and Miri Make a Porno (2008)
★ 6.3/10Also comedy and romanceLifelong platonic friends Zack and Miri look to solve their respective cash-flow problems by making an adult film together. As the cameras roll, however, the duo begin to sense that they may have more feelings for each…
- 11
That Awkward Moment (2014)
★ 6.1/10Also comedy and romanceBest pals Jason and Daniel indulge in casual flings and revel in their carefree, unattached lives. After learning that the marriage of their friend Mikey is over, they gladly welcome him back into their circle. The…
- 12
Mr. Jealousy (1998)
★ 5.9/10Also comedy and romanceAfter his first date at age 15 ended with the girl making out with another man at a party, aspiring writer Lester Grimm has treated all his girlfriends with jealousy and suspicion. While dating Ramona Ray, paranoia…
- 13
The Incredible Jessica James (2017)
★ 6.1/10Also romance and comedyBurned by a bad breakup, a struggling New York City playwright makes an unlikely connection with a divorced app designer she meets on a blind date.
- 14
How I Got Into College (1989)
★ 6/10Also comedy and romanceHigh school senior Marlon Bowne is smitten with overachieving classmate Jessica Kailo. But, if he wants to have a shot with her, he'll have to find a way to get into Ramsey College, Jessica's top choice of schools. It…
- 15
Someone Great (2019)
★ 6.4/10Also comedy and romanceAn aspiring music journalist lands her dream job and is about to move to San Francisco when her boyfriend of nine years decides to call it quits. To nurse her broken heart, she and her two best friends spend one…
- 16
Splendor (1999)
★ 6.2/10Also comedy and romanceVeronica is a white-bread beauty searching for a good man in Los Angeles. While slam dancing at a Halloween rave, she meets Abel, a sensitive poet. Then she meets Zed, a supersexy tattooed drummer with incredible…
- 17
No Hard Feelings (2023)
★ 6.7/10Also comedy and romanceOn 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…
- 18
French Girl (2024)
★ 6.2/10Also romance and comedySweet Gordon, an affable English teacher in Brooklyn, has beaten the odds; a French Girl has fallen in love with him and he’s fallen even harder back. But their future is thrown into limbo when she interviews for an…
- 19
Mischief (1985)
★ 6.7/10Also comedy and romance1956: The shy Jonathan's luck with girls changes when he wins the rebellious Gene as a friend in his last year of high school. Gene is adored by many girls and manages to teach Jonathan a few lessons. Gene himself…
- 20
Office Romance (2026)
★ 6.4/10Also romance and comedyJackie, President and CEO of Air Cruz, runs a tight ship in her business, including a rigid anti-fraternization policy for all her employees. When a new sexy lawyer begins working for her, that policy becomes very…