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Movies like That Awkward Moment (2014)

The best movies like That Awkward Moment (2014) are My Fake Boyfriend (2022), Bye Bye Love (1995) and ¿Quieres ser mi hijo? (2023). If That Awkward Moment hooked you with its comedy and romance, these 30 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. 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

  2. Bye Bye Love (1995)

    With varying degrees of success, recently divorced friends Dave, Vic and Donny are trying to move on with their lives. Vic feels vilified by his ex-wife's parents, while Donny has a shaky bond with his teen daughter, Emma. Dave, meanwhile, has an enviable problem -- he has more dates than he can handle. As they confront their post-marital challenges, the men take solace in one another's plights.

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

    Popcorn FlickMovies like this
  3. ¿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
  4. About Last Night (2014)

    Bernie and Joan are two fiery flirters who are passionate about everything from hookups to breakups and each other. When he sets up his best friend, Danny, with her roommate, Debbie, the sparks soon fly as they try to navigate the relationship minefields from the bar to the bedroom and are eventually put to the test in the real world.

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

    Popcorn FlickMovies like this
  5. The Perfect Date (2019)

    No beau? No problem! To earn money for college, a high schooler creates a dating app that lets him act as a stand-in boyfriend.

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

    Popcorn FlickMovies like this
  6. 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
  7. Zack and Miri Make a Porno (2008)

    Lifelong 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 other than they previously thought.

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

    Popcorn FlickMovies like this
  8. The Long Weekend (2005)

    Cooper 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 brother hooked up with a girl, thus a long weekend of stress and beautiful women, culminating in Ed meeting, and making love to, the woman of his dreams.

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

  9. 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
  10. Someone Like You... (2001)

    Jane Goodale has everything going for her. She's a producer on a popular daytime talk show, and is in a hot romance with the show's dashing executive producer Ray. But when the relationship goes terribly awry, Jane begins an extensive study of the male animal, including her womanizing roommate Eddie. Jane puts her studies and romantic misadventure to use as a pseudonymous sex columnist -- and becomes a sensation.

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

    Popcorn FlickMovies like this
  11. 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
  12. No 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: Recommended by TMDB viewers · both comedy & romance

    Popcorn FlickMovies like this
  13. 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
  14. Friends with Benefits (2011)

    Dylan is done with relationships. Jamie decides to stop buying into the Hollywood clichés of true love. When the two become friends they decide to try something new and take advantage of their mutual attraction - but without any emotional attachment.

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

    Popcorn FlickMovies like this
  15. 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
  16. The 40 Year-Old Virgin (2005)

    Andy Stitzer has a pleasant life with a nice apartment and a job stamping invoices at an electronics store. But at age 40, there's one thing Andy hasn't done, and it's really bothering his sex-obsessed male co-workers: Andy is still a virgin. Determined to help Andy get laid, the guys make it their mission to de-virginize him. But it all seems hopeless until Andy meets small business owner Trish, a single mom.

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

    Popcorn FlickMovies like this
  17. Desperados (2020)

    A 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.

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

    Popcorn FlickMovies like this
  18. 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

  19. The Climb (2020)

    Kyle and Mike are best friends who share a close bond — until Mike sleeps with Kyle’s fiancée. A stormy but enduring relationship ensues between Kyle, with limitless patience, and Mike, who only lives his life by sowing discord in that of others, across many years of laughter, heartbreak, and rage.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  20. 72 HOURS (2026)

    To save his career, a 40-year-old ad exec joins a crew of twentysomethings for a wild Miami bachelor party after they mistakenly add him to a group chat.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  21. Mystic Pizza (1988)

    Three teenage girls come of age while working at a pizza parlor in Mystic, Connecticut.

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

    Popcorn FlickMovies like this
  22. I Often Think of Piroschka (1955)

    Andreas, a young German student comes to Hungary on an exchange programme. In the Hungarian village he falls in love with the stationmaster's daughter Piroschka and spends much of his time with her. They have an enchanting summer until Andreas gets an invitation to join another young woman at a nearby resort. Piroschka is jealous and follows him there, causing trouble. It takes a long time for Andreas and Piroschka to even talk to each other again. When Andreas has to leave Hungary at the end of his holiday, he is determined to return some day.

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

  23. Livin' with the Devil (2025)

    After a recent breakup, a couple finds themselves financially trapped under the same roof, navigating the complexities of living together while separated.

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

  24. Grumpy Old Men (1993)

    For decades, next-door neighbors and former friends John and Max have feuded, trading insults and wicked pranks. When an attractive widow moves in nearby, their bad blood erupts into a high-stakes rivalry full of naughty jokes and adolescent hijinks.

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

    Popcorn FlickMovies like this
  25. Must Love Dogs (2005)

    Sarah Nolan is a newly divorced woman cautiously rediscovering romance with the enthusiastic but often misguided help of her well-meaning family. As she braves a series of hilarious disastrous mismatches and first dates, Sarah begins to trust her own instincts again and learns that, no matter what, it's never a good idea to give up on love.

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

  26. The Sweetest Thing (2002)

    Christina's love life is stuck in neutral. After years of avoiding the hazards of a meaningful relationship, one night while club-hopping with her girlfriends, she meets Peter, her perfect match. Fed up with playing games, she finally gets the courage to let her guard down and follow her heart, only to discover that Peter has suddenly left town. Accompanied by Courtney, she sets out to capture the one that got away.

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

  27. St. Elmo's Fire (1985)

    Reluctant to let go of college life, a close-knit team of seven friends--irresponsible saxophone player Billy, young Republican Alec, his girlfriend Leslie, struggling journalist Kevin, drama queen Jules, lovesick waiter Kirby, and Wendy, a social worker with a heart of gold--realise the party is over. And as the burdens of maturity close in on the young dreamers, the complexities of adulthood and the daily struggle of growing up put their sacred friendship to the test. But everyone knows life is not a bed of roses. It won't be easy, but when all is said and done, what will it take for St. Elmo's clique to find its place in the real world?

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

    Popcorn FlickMovies like this
  28. 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
  29. Pete's Dragon (1977)

    Pete, a young orphan, runs away to a Maine fishing town with his best friend a lovable, sometimes invisible dragon named Elliott! When they are taken in by a kind lighthouse keeper, Nora, and her father, Elliott's prank playing lands them in big trouble. Then, when crooked salesmen try to capture Elliott for their own gain, Pete must attempt a daring rescue.

    Why it matches: Similar story and style · both comedy

    Popcorn FlickMovies like this
  30. Strangers in the Park (2026)

    A former communist militant and a "live and let live" man form an unlikely friendship on a park bench, sharing their life stories with humor and heart.

    Why it matches: Similar story and style · both comedy

Like That Awkward Moment and something else?

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

Frequently asked questions

What are the best movies like That Awkward Moment?

The closest matches to That Awkward Moment are My Fake Boyfriend (2022), Bye Bye Love (1995) and ¿Quieres ser mi hijo? (2023). Below are 27 more, each with the reason it matches.

What should I watch after That Awkward Moment?

Start with My Fake Boyfriend (2022), the closest match to That Awkward Moment.

What is the highest-rated movie like That Awkward Moment?

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

What is the newest movie like That Awkward Moment?

72 HOURS (2026) is the most recent release on this list.

Are there English movies like That Awkward Moment?

Yes: My Fake Boyfriend (2022), Bye Bye Love (1995) and ¿Quieres ser mi hijo? (2023).

How are movies similar to That Awkward Moment chosen?

First come films that Trakt’s viewers watch alongside That Awkward Moment, 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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