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That Awkward Moment poster

Movies that feel likeThat 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.

If you loved That Awkward Moment, the closest films we have are Yeh Jawaani Hai Deewani (2013), No Hard Feelings (2023) and Ask Me If I'm Happy (2000). All three share That Awkward Moment's witty and playful feel, which is what we rank on before quality.

Seen the big three already? The under-the-radar pick below is Queen (2014).

🍅 23% Rotten Tomatoes★ 6.1 IMDb ↗TMDB ↗dir. Tom Gormicanwittyplayfulromanticwarm
10 of 12 streaming nowNetflix · HBO Max · Amazon Prime Video

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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
🍅 69%★ 7.3romance · comedyNetflixPrime Video

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.

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

One thread runs through both: friendship

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.

Ask Me If I'm Happy poster
Ask Me If I'm Happy
2000 · dir. Giacomo Poretti
★ 7.2comedy

Both keep coming back to the same thing: male friendship

Aspiring thespians Aldo, Giovanni and Giacomo work dead-end jobs while nurturing their dream production of Cyrano de Bergerac, until love for the same woman tears their friendship apart. Three years later, Giovanni and Giacomo reunite after learning that Aldo is dying.

Bridesmaids poster
Bridesmaids
2011 · dir. Paul Feig
🍅 89%★ 6.8comedy · romancePrime Video

Witty and playful in the same breath

Annie's life is a mess. But when she finds out her lifetime best friend is engaged, she simply must serve as Lillian's maid of honor. Though lovelorn and broke, Annie bluffs her way through the expensive and bizarre rituals. With one chance to get it perfect, she’ll show Lillian and her bridesmaids just how far you’ll go for someone you love.

Friends with Benefits poster
Friends with Benefits
2011 · dir. Will Gluck
🍅 69%★ 6.5romance · comedy

Both land romance and warmth at once

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

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.

Bride Wars poster
Bride Wars
2009 · dir. Gary Winick
🍅 10%★ 5.5comedy · romanceParamount+

Witty comedy, and it commits to that

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

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

Common ground: 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.

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

Romance with a pulse of play, in both cases

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.

Mr. Deeds poster
Mr. Deeds
2002 · dir. Steven Brill
🍅 22%★ 5.8comedy · romance

Romantic comedy in both cases

When Longfellow Deeds, a small-town pizzeria owner and poet, inherits $40 billion from his deceased uncle, he quickly begins rolling in a different kind of dough. Moving to the big city, Deeds finds himself besieged by opportunists all gunning for their piece of the pie. Babe, a television tabloid reporter, poses as an innocent small-town girl to do an exposé on Deeds.

Queen poster
Queen
2014 · dir. Vikas Bahl
🍅 90%★ 8.1comedy · drama

Both lean on warmth more than on romance

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

Rani, a 24-year-old homely girl, decides to go on her honeymoon alone when her fiancé calls off the wedding. Traveling around Europe, she finds joy, makes friends, and gains new-found independence.

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

Both are built on the same subject: relationship

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.

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The best-reviewed films that share That Awkward Moment’s defining feeling.