Awkward Comedy backdrop

Awkward Comedy movies

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

Where Am I Going?

1. Where Am I Going?

Comedy Family Adventure Awkward Comedy Parent-Child Family
6.7
20161h 26min

Overview

Checco is 39 and lived his entire life with his parents. He loves his job where he does nothing the whole day, until something happens that will change his behavior and his life forever...

Themes

Deception and framing, Teamwork under threat, Guardianship and protection, Belonging through crisis, Relocation under danger, Alien outsider status

Available on

Netflix
Disney Plus
Amazon Prime Video
Data provided by JustWatch.Availability may vary by region.

Sisters

2. Sisters

Comedy Awkward Comedy
6.0
20151h 58min

Overview

Two disconnected sisters are summoned to clean out their childhood bedrooms before their parents sell their family home.

Themes

Sibling relationship strain, Childhood home pressure, Family home sale anxiety, Parental boundary negotiation, Public disruption vs privacy, Old life new beginnings

Available on

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

The Dressmaker

3. The Dressmaker

Drama Comedy Western Historical Drama Awkward Comedy
7.0
20151h 58min

Overview

In 1950s Australia, beautiful, talented dressmaker Tilly returns to her tiny hometown to right wrongs from her past. As she tries to reconcile with her mother, she starts to fall in love while transforming the fashion of the town.

Themes

Deception and exposure, Small-town judgment, Fashion as agency, Gender and craft, Heritage and kinship, Class and power

Available on

Amazon Prime Video
Google Play Movies
YouTube
Data provided by JustWatch.Availability may vary by region.

People, Places, Things

4. People, Places, Things

Romance Comedy Drama Romantic Comedy Awkward Comedy
6.8
20151h 25min

Overview

Will Henry thinks he’s just juggling a breakup, his twin daughters, and a new crush—until one question sinks its hooks in: what if he really was the problem? Now every class, every visit, every date turns into evidence in a case against himself… and he can’t stop digging.

Themes

Writer as artist, New york city pressures, Divorce and reinvention, Pizza motif in relationships, Parent child balance, Letting go dynamics

Available on

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

Mistress America

5. Mistress America

Comedy Awkward Comedy
6.7
20151h 24min

Overview

A college freshman cures her disappointment and loneliness by allowing herself to be pulled into the wacky schemes of her future stepsister.

Themes

Class inequality, Deception and perception, Ambition and dependence, Female friendship dynamics, Creative validation and risk, Urban aspiration and domestic security

Available on

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

The Diary of a Teenage Girl

6. The Diary of a Teenage Girl

Drama Romance Comedy Coming-of-Age Drama Coming-of-Age Romance
6.8
20151h 42min

Overview

Minnie Goetze is a 15-year-old aspiring comic-book artist, coming of age in the haze of the 1970s in San Francisco. Insatiably curious about the world around her, Minnie is a pretty typical teenage girl. Oh, except that she’s sleeping with her mother’s boyfriend.

Themes

Autonomy vs dependence, Age gap dynamics, Coming of age sexuality, Experimentation and boundary testing, Art as self expression, Bohemian domestic tension, Self-acceptance and independence

Available on

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

Jenny's Wedding

7. Jenny's Wedding

Comedy Drama Family Drama Awkward Comedy
5.6
20151h 34min

Overview

Jenny Farrell is getting married. But how will her straight-laced family react when they find out that the woman they thought was their daughter’s roommate is actually her fiancée? As the old-fashioned Farrells attempt to come to terms with the prospect of a surprise daughter-in-law, they face a difficult choice: either adapt with the times or risk being left behind.

Themes

Coming out pressures, Lgbt family dynamics, Wedding as social test, Generational change vs tradition, Parental pride and conflict, Lesbian visibility

Available on

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

Trainwreck

8. Trainwreck

Comedy Romance Romantic Comedy Awkward Comedy
6.2
20152h 5min

Overview

Having thought that monogamy was never possible, a commitment-phobic career woman may have to face her fears when she meets a good guy.

Themes

Fear of commitment, Career versus romance, Public scrutiny of romance, Self-destructive dating patterns, Family obligation vs romance, Personal growth and change

Available on

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

Some Kind of Beautiful

9. Some Kind of Beautiful

Comedy Romance Romantic Comedy Awkward Comedy
5.7
20151h 39min

Overview

By day, Richard Haig is a successful and well-respected English professor at renowned Trinity College in Cambridge. By night, Richard indulges his own romantic fantasies with a steady stream of beautiful undergraduates. But Richard has grown tired of the game and is looking for something more meaningful and lasting. So when Kate, Richard’s tanned, athletic, 25-year-old American girlfriend tells him that she is pregnant, Richard is thrilled. He looks forward to having a family of his own, being a father his children could be proud of, not some sex-fueled bobcat. There is only one problem. Richard’s not in love with Kate. Richard is in love with Kate’s sister, Olivia. He had been in love with her ever since he first saw her.

Themes

Infidelity and deception, Career vs personal life, Age-gap romance, Teacher-student dynamic, Parental duty and care, Search for lasting connection

Available on

Google Play Movies
YouTube
Plex Channel
Data provided by JustWatch.Availability may vary by region.

Sleeping with Other People

10. Sleeping with Other People

Comedy Romance Romantic Comedy Awkward Comedy
6.5
20151h 40min

Overview

Can two serial cheaters get a second chance at love? After a one-night stand in college, New Yorkers Lainey and Jake meet by chance twelve years later and discover they each have the same problem: because of their monogamy-challenged ways, neither can maintain a relationship. Determined to stay friends despite their mutual attraction, they make a pact to keep it platonic, a deal that proves easier said than done.

Themes

Loyalty under pressure, Commitment issues, Career vs romance, Friends to lovers, Deception and desire, Casual dating expectations

Available on

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