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Movies that feel like That Awkward Moment (2014)

If you loved That Awkward Moment, the closest films we have are Yeh Jawaani Hai Deewani (2013), He's Just Not That Into You (2009) and This Means War (2012). All three share That Awkward Moment's witty and playful feel, which is what we rank on before quality. 10 of the 12 picks below are included with a subscription right now on Netflix, HBO Max and Amazon Prime Video and others, checked against today's data.

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.

🍅 23% Rotten Tomatoes6.1 IMDb ↗TMDB ↗dir. Tom Gormicanwittyplayfulromantictenderwarm

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If That Awkward Moment hit the spot, these will too

Yeh Jawaani Hai Deewani poster
Yeh Jawaani Hai Deewani
2013 · dir. Ayan Mukerji
🍅 64%7.3romance · comedy

The same two preoccupations: friendship, and relationship

The difference: Critics rated this one higher still

On a trekking trip, an introverted Naina falls for a charming ex-classmate, whose thirst for adventure drives them apart. Years later, their paths cross again.

He's Just Not That Into You poster
He's Just Not That Into You
2009 · dir. Ken Kwapis
🍅 42%6.4comedy · romance · drama

Both keep coming back to the same thing: friendship

The difference: Sits closer to drama than That Awkward Moment does

Remember that really cute girl/guy who said they'd call – and didn't? Maybe they lost your number. Maybe they're in the hospital. Maybe they're awed by your looks, brains or success. Or maybe... They're just not that into you.

This Means War poster
This Means War
2012 · dir. McG
🍅 24%6.3action · comedy · romance

One thread runs through both: dating

The difference: Leans harder into action than That Awkward Moment does

Two top CIA operatives wage an epic battle against one another after they discover they are dating the same woman.

Bride Wars poster
Bride Wars
2009 · dir. Gary Winick
🍅 10%5.5comedy · romance

The same mix in both: wit, then play

Two best friends become rivals when their respective weddings are accidentally booked for the same day.

Drinking Buddies poster
Drinking Buddies
2013 · dir. Joe Swanberg
🍅 84%6.1romance · drama · comedy

The same preoccupation in both: relationship

The difference: Missing the warmth of That Awkward Moment

Weekend trips, office parties, late night conversations, drinking on the job, marriage pressure, biological clocks, holding eye contact a second too long… you know what makes the line between “friends” and “more than friends” really blurry? Beer.

Adventureland poster
Adventureland
2009 · dir. Greg Mottola
🍅 89%6.8comedy · drama · romance

Common ground: young adult

It's the summer of 1987, and recent college grad James Brennan can't wait to begin his long-anticipated dream trip to Europe. Unfortunately, James' plans come to a screeching halt when his parents announce that they are unable to subsidize his trip. Forced to take a job at the local amusement park, James prepares for the worst summer ever, until he finds love with a captivating co-worker named Em.

No Hard Feelings poster
No Hard Feelings
2023 · dir. Gene Stupnitsky
🍅 71%6.3comedy · romance

Both land romance and tenderness at once

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.

She's Out of My League poster
She's Out of My League
2010 · dir. Jim Field Smith
🍅 57%6.4romance · comedy

Both are built on the same subject: dating

When he starts dating drop-dead gorgeous Molly, insecure airport security agent Kirk can't believe it. As his friends and family share their doubts about the relationship lasting, Kirk does everything he can to avoid losing Molly forever.

Just Go with It poster
Just Go with It
2011 · dir. Dennis Dugan
🍅 20%6.4comedy · romance

Warm comedy, and it commits to that

While romancing Palmer, a much younger schoolteacher, plastic surgeon Danny Maccabee enlists his loyal assistant Katherine to pretend to be his soon to be ex-wife, in order to cover up a careless lie. When more lies backfire, Katherine's kids become involved, and everyone heads off for a weekend in Hawaii that will change all their lives.

Crazy, Stupid, Love. poster
Crazy, Stupid, Love.
2011 · dir. Glenn Ficarra
🍅 79%7.4comedy · drama · romance

Romance built on wit, twice over

Cal Weaver is living the American dream. He has a good job, a beautiful house, great children and a beautiful wife, named Emily. Cal's seemingly perfect life unravels, however, when he learns that Emily has been unfaithful and wants a divorce. Over 40 and suddenly single, Cal is adrift in the fickle world of dating. Enter, Jacob Palmer, a self-styled player who takes Cal under his wing and teaches him how to be a hit with the ladies.

Bridget Jones: The Edge of Reason poster
Bridget Jones: The Edge of Reason
2004 · dir. Beeban Kidron
🍅 27%6comedy · romance

Comedy with a pulse of play, in both cases

Bridget Jones is still dating her new love, barrister Mark Darcy, for a perfect six weeks. However, while on assignment in Thailand with her disreputable ex, Daniel Cleaver, claiming to be reformed, Bridget questions if she has everything she's ever dreamed of having.

The 40 Year-Old Virgin poster
The 40 Year-Old Virgin
2005 · dir. Judd Apatow
🍅 85%7.1comedy · romance

The same preoccupation in both: male friendship

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.

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