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Movies like You, Me, and Annamarie (2023)

The best movies like You, Me, and Annamarie (2023) are That Awkward Moment (2014), My Fake Boyfriend (2022) and Playing It Cool (2014). If You, Me, and Annamarie 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

  1. That Awkward Moment (2014)

    Best 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 three young men make a pact to have fun and avoid commitment. However, when all three find themselves involved in serious relationships, they must keep their romances secret from one another.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

    Popcorn FlickMovies like this
  2. My Fake Boyfriend (2022)

    A young man in a tricky situation follows the advice of his unconventional best friend and uses social media to create a fake boyfriend to keep his awful ex-lover out of his life. But everything backfires when he meets the real love of his life, and breaking up with his fake boyfriend proves hard to do.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

  3. Playing It Cool (2014)

    A young man meets and instantly falls in love with an engaged woman.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

  4. Do Revenge (2022)

    A dethroned queen bee at a posh private high school strikes a secret deal with an unassuming new student to enact revenge on one another’s enemies.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

    Popcorn FlickMovies like this
  5. How to Date Billy Walsh (2024)

    Archie has been in love with his best friend Amelia for as long as he can remember. Just when he builds up the courage to declare his feelings, she falls head over heels for Billy Walsh, a new American transfer student.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

    Popcorn FlickMovies like this
  6. The Night Before (1988)

    A popular beauty surprisingly asks a nerd to take her to the prom. He wakes up hours later in a sleazy alley. She's missing but he remembers nothing about it.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

    Popcorn FlickMovies like this
  7. I Want You Back (2022)

    Peter and Emma thought they were on the precipice of life’s biggest moments – marriage, kids, and houses in the suburbs – until their respective partners dumped them. Horrified to learn that the loves of their lives have already moved on, Peter and Emma hatch a hilarious plan to win back their exes with unexpected results.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

    Popcorn FlickMovies like this
  8. Sex Drive (2008)

    A high school senior drives cross-country with his best friends to hook up with a babe he met online.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

    Popcorn FlickMovies like this
  9. A Simple Favor (2018)

    Stephanie, a dedicated mother and popular vlogger, befriends Emily, a mysterious upper-class woman whose son Nicky attends the same school as Miles, Stephanie's son. When Emily asks her to pick Nicky up from school and then disappears, Stephanie undertakes an investigation that will dive deep into Emily's cloudy past.

    Why it matches: Recommended by TMDB viewers · both comedy & mystery

    Popcorn FlickMovies like this
  10. Players (2024)

    New 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 for keeps.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

    Popcorn FlickMovies like this
  11. Sex Appeal (2022)

    Avery, a teenager with a tendency towards perfectionism, enlists her friend Larson to help her prepare for her first time with her long-distance boyfriend.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

    Popcorn FlickMovies like this
  12. ¿Quieres ser mi hijo? (2023)

    Lu, 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.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

    Absolute CinemaMovies like this
  13. Sidelined 2: Intercepted (2025)

    Freshman star quarterback Drayton struggles with the weight of expectations after a devastating setback, while dancer Dallas begins to question the future she thought she wanted. As their high school relationship begins to unravel under the pressures of distance and self-discovery, they’ll learn that the bravest versions of themselves emerge when they let life redirect them.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

    Worth the HypeMovies like this
  14. Splendor (1999)

    Veronica 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 biceps. Who will she choose? Does she go for true love or cheap sex? She can't decide so she chooses both. But after managing to nurture a picture-perfect threesome, along comes Ernest, a rich movie director with deep baby blues that sweep Veronica off her feet. What's a girl to do now?

    Why it matches: Recommended by TMDB viewers · both comedy & romance

    Popcorn FlickMovies like this
  15. The Last Summer (2019)

    Standing on the precipice of adulthood, a group of friends navigate new relationships, while reexamining others, during their final summer before college.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

    Popcorn FlickMovies like this
  16. Someone Great (2019)

    An 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 outrageous last adventure in New York City.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

    Popcorn FlickMovies like this
  17. How I Got Into College (1989)

    High 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 won't be easy, since the college is highly selective and Marlon's grades are hardly impressive. That means the lovelorn teen will have to find a way to score high on the SATs and win over the college admissions committee.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

    Popcorn FlickMovies like this
  18. Revenge of the Bridesmaids (2010)

    Two women plot revenge against the woman marrying their friend's ex-boyfriend.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

    Popcorn FlickMovies like this
  19. Dinner in America (2022)

    An on-the-lam punk rocker and a young woman obsessed with a local band go on an unexpected and epic journey together through the decaying suburbs of the American Midwest.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

    Worth the HypeMovies like this
  20. A Nice Girl Like You (2020)

    Lucy 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 of self-discovery, friendship, and new love.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

  21. The Prince & Me (2004)

    A fairy tale love-story about pre-med student Paige who falls in love with a Danish Prince "Eddie" who refused to follow the traditions of his parents and has come to the US to quench his thirst for rebellion. Paige and Edward come from two different worlds, but there is an undeniable attraction between them.

    Why it matches: Similar story and style · both comedy & romance

    Popcorn FlickMovies like this
  22. The Seekers: Thrill Night (2021)

    On Halloween, estranged friends Asger and Esther, must work together to rescue Asgers kidnapped sister Petra, while Petra battles the thieves that took her.

    Why it matches: Similar story and style · both mystery & comedy

  23. Dumb and Dumberer: When Harry Met Lloyd (2003)

    This wacky prequel to the 1994 blockbuster goes back to the lame-brained Harry and Lloyd's days as classmates at a Rhode Island high school, where the unprincipled principal puts the pair in remedial courses as part of a scheme to fleece the school.

    Why it matches: Similar story and style · both comedy

  24. White Men Can't Jump (1992)

    Two street basketball hustlers try to con each other, then team up for a bigger score.

    Why it matches: Similar story and style · both comedy

    Popcorn FlickMovies like this
  25. D3: The Mighty Ducks (1996)

    The Ducks are offered scholarships at Eden Hall Academy but struggle with their new coach's methods and come under pressure from the board to retain their scholarships before their big game against the Varsity team.

    Why it matches: Similar story and style · both comedy

    Popcorn FlickMovies like this
  26. Wonder Boys (2000)

    Grady is a 50-ish English professor who hasn't had a thing published in years—not since he wrote his award winning 'Great American Novel' 7 years ago. This weekend proves even worse than he could imagine as he finds himself reeling from one misadventure to another in the company of a new wonder boy author.

    Why it matches: Similar story and style · both comedy

    Popcorn FlickMovies like this
  27. Smokey and the Bandit (1977)

    A race car driver tries to transport an illegal beer shipment from Texas to Atlanta in under 28 hours, picking up a reluctant bride-to-be on the way.

    Why it matches: Similar story and style · both comedy

    Worth the HypeMovies like this
  28. India (1993)

    Heinzi Boesel and Kurt Fellner are two Austrian health inspectors forced to work together, traveling through Austria. Over time a beautiful friendship evolves between the odd couple who couldn't stand each other initially; a friendship that even overcomes the boundaries of great tragedy.

    Why it matches: Similar story and style · both comedy

    Worth the HypeMovies like this
  29. The University of Las Colinas (2020)

    A group of troublemakers go back to school to avoid jail.

    Why it matches: Similar story and style · both comedy

  30. See No Evil, Hear No Evil (1989)

    A murder takes place in the shop of David Lyons, a deaf man who fails to hear the gunshot being fired. Outside, blind man Wally Karue hears the shot, but cannot see the perpetrator. Both are arrested, but escape to form an unlikely partnership. Being chased by both the law AND the original killers, can the pair work together to outwit them all?

    Why it matches: Similar story and style · both comedy

    Popcorn FlickMovies like this

Like You, Me, and Annamarie and something else?

Blend two favourites and we’ll find the films in between.

Frequently asked questions

What are the best movies like You, Me, and Annamarie?

The closest matches to You, Me, and Annamarie are That Awkward Moment (2014), My Fake Boyfriend (2022) and Playing It Cool (2014). Below are 27 more, each with the reason it matches.

What should I watch after You, Me, and Annamarie?

Start with That Awkward Moment (2014), the closest match to You, Me, and Annamarie.

What is the highest-rated movie like You, Me, and Annamarie?

¿Quieres ser mi hijo? (2023), rated 8.4/10 by 378 TMDB users.

What is the newest movie like You, Me, and Annamarie?

Sidelined 2: Intercepted (2025) is the most recent release on this list.

Are there English movies like You, Me, and Annamarie?

Yes: That Awkward Moment (2014), My Fake Boyfriend (2022) and Playing It Cool (2014).

How are movies similar to You, Me, and Annamarie chosen?

First come films that Trakt’s viewers watch alongside You, Me, and Annamarie, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.

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