Awkward Comedy backdrop

Awkward Comedy movies

Cringe-powered, character-based humor: misreads, social discomfort, odd sincerity, and painfully funny situations.

Bring It On: Fight to the Finish

1. Bring It On: Fight to the Finish

Comedy Awkward Comedy
5.2
20091h 42min

Overview

When her mother falls for a wealthy man, Lina Cruz must move in with her new stepfather and transfer from an urban East Los Angeles public high school to an exclusive prep school in Malibu, where she struggles to fit in with her affluent new peers. After snooty cheerleading captain Avery blocks Lina from varsity, Lina recruits her best friends from her old school to help her whip the pathetic junior varsity cheerleading squad -- the Sea Lions -- into fighting shape.

Themes

Deception and manipulation, Economic disparity, Teamwork under stress, Social adaptation, Competitive pressure, Outsider vs insider

Available on

Amazon Video
Apple TV
Google Play Movies
Data provided by JustWatch.Availability may vary by region.

The Ugly Truth

2. The Ugly Truth

Comedy Romance Romantic Comedy Awkward Comedy
6.4
20091h 36min

Overview

A romantically challenged morning show producer is reluctantly embroiled in a series of outrageous tests by her chauvinistic correspondent to prove his theories on relationships and help her find love. His clever ploys, however, lead to an unexpected result.

Themes

Gender dynamics under pressure, Performative dating, Self-help culture, Ratings-driven romance, Manipulation in dating advice, Opposites attract

Available on

Netflix
Amazon Video
Apple TV
Data provided by JustWatch.Availability may vary by region.

Frequently Asked Questions About Time Travel

3. Frequently Asked Questions About Time Travel

Comedy Drama Romance Science Fiction Awkward Comedy
7.0
20091h 23min

Overview

Follows three social outcasts -- two geeks and a cynic -- as they attempt to navigate a time-travel conundrum in the middle of a British pub.

Themes

Deception and manipulation, Time travel consequences, Group dynamics under pressure, Editorial censorship, Memory across timelines, Art and cultural standards

Available on

Amazon Video
Apple TV
HBO Max
Data provided by JustWatch.Availability may vary by region.

I Love You, Man

4. I Love You, Man

Comedy Romance Awkward Comedy Romantic Comedy
7.0
20091h 45min

Overview

Peter Klaven is a successful real estate agent who, upon getting engaged to the woman of his dreams, Zooey, discovers, to his dismay and chagrin, that he has no male friend close enough to serve as his Best Man. Peter immediately sets out to rectify the situation, embarking on a series of bizarre and awkward "man-dates."

Themes

Male friendship deficit, Performative masculinity, Marriage social pressure, Awkward social performance, Social signaling through weddings, Public image through advertising, Loyalty and friendship repair

Available on

Amazon Video
Apple TV
Google Play Movies
Data provided by JustWatch.Availability may vary by region.

Bride Wars

5. Bride Wars

Comedy Romance Romantic Comedy Awkward Comedy
5.5
20091h 29min

Overview

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

Themes

Friendship under pressure, Reputation vs authenticity, Public judgment and rituals, Wedding rivalry, Self-assertion in relationships, Manipulation in social settings

Available on

Netflix
Amazon Video
Apple TV
Data provided by JustWatch.Availability may vary by region.

Love Exposure

6. Love Exposure

Action Comedy Drama Romance Awkward Comedy
8.0
20083h 57min

Overview

The story of a teenage boy named Yu, who falls for Yoko, a girl he runs into while operating for the sake of sin as an "up-skirt" photographer. His attempts to woo her are complicated by a spot of cross-dressing – which convinces Yoko that she is lesbian – dalliances with kung-fu and crime, and a constant struggle with the guilt that's a legacy of his Catholic upbringing.

Themes

Forbidden romance, Religious expectation, Transvestite disguise, Cross dressing, Disguised self, Cult manipulation

Available on

Amazon Prime Video
Filmin
ARROW
Data provided by JustWatch.Availability may vary by region.

Step Brothers

7. Step Brothers

Comedy Awkward Comedy
6.9
20081h 38min

Overview

Brennan Huff and Dale Doback might be grown men. But that doesn't stop them from living at home and turning into jealous, competitive stepbrothers when their single parents marry. Brennan's constant competition with Dale strains his mom's marriage to Dale's dad, leaving everyone to wonder whether they'll ever see eye to eye.

Themes

Becoming an adult, Childhood trauma, Stepbrother dynamics, Slacker identity, Class discrimination, Autonomy vs dependence

Available on

Amazon Video
Apple TV
Google Play Movies
Data provided by JustWatch.Availability may vary by region.

My Sassy Girl

8. My Sassy Girl

Comedy Romance Romantic Comedy Awkward Comedy
6.2
20081h 32min

Overview

A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.

Themes

Volatile personality dynamics, Responsibility and care, Past relationship reenactment, Familial opposition, Turbulent romance, Destiny and timing

Available on

Shout! Factory TV
Plex
Plex Channel
Data provided by JustWatch.Availability may vary by region.

Happy-Go-Lucky

9. Happy-Go-Lucky

Comedy Drama Awkward Comedy Coming-of-Age Drama
7.0
20081h 58min

Overview

A look at a few chapters in the life of Poppy, a cheery, colorful, North London schoolteacher whose optimism tends to exasperate those around her.

Themes

Optimism vs exasperation, Care for at-risk youth, Family expectations and choice, Romantic tension and boundaries, Bias and intolerance

Available on

Amazon Video
Apple TV
Google Play Movies
Data provided by JustWatch.Availability may vary by region.

Charlie Bartlett

10. Charlie Bartlett

Comedy Drama Romance Awkward Comedy Coming-of-Age Drama
6.9
20081h 37min

Overview

Awkward teenager Charlie Bartlett has trouble fitting in at a new high school. Charlie needs some friends fast, and decides that the best way to find them is to appoint himself the resident psychiatrist. He becomes one of the most popular guys in school by doling out advice and, occasionally, medication, to the student body.

Themes

High school pressure, Drug addiction dynamics, Adolescent depression, Private school divide, Suicide attempt challenges, Psychiatrist role

Available on

Amazon Video
Apple TV
Google Play Movies
Data provided by JustWatch.Availability may vary by region.