That Awkward Moment
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.
Movies Like That Awkward Moment
Similar in style, tone, and themes — find your next watch.
My Fake Boyfriend
2022★ 5.9
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.
Bye Bye Love
1995★ 6.0
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.
¿Quieres ser mi hijo?
2023★ 8.5
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.
Sex Appeal
2022★ 6.6
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.
About Last Night
2014★ 6.0
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.
Zack and Miri Make a Porno
2008★ 6.3
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.
Players
2024★ 6.1
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.
The Climb
2020★ 6.1
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.
Teacher's Pet
1958★ 6.8
A rugged city editor poses as a journalism student and flirts with the professor.
The Best Man Holiday
2013★ 6.5
When college friends reunite after 15 years over the Christmas holidays, they discover just how easy it is for long-forgotten rivalries and romances to be reignited.
No Hard Feelings
2023★ 6.7
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.
Someone Like You...
2001★ 6.0
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.
All Over the Guy
2001★ 5.8
A contemporary romantic comedy exploring the unlikely pairing of two 20-somethings thrown together by their respective best friends in hopes of igniting their own romance.
Desperados
2020★ 6.0
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.
Splendor
1999★ 6.1
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?
Friends with Benefits
2011★ 6.6
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.
The 40 Year Old Virgin
2005★ 6.4
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.
How I Got Into College
1989★ 6.0
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.
I Want You Back
2022★ 6.3
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.
Playing It Cool
2014★ 5.8
A young man meets and instantly falls in love with an engaged woman.