Awkward Comedy backdrop

Awkward Comedy movies

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

Chalet Girl

1. Chalet Girl

Comedy Romance Romantic Comedy Awkward Comedy
6.3
20111h 37min

Overview

While working a job at an exclusive ski resort to support her Dad, Kim learns to snowboard and is so good at it that she enters a competition with a huge cash prize. She has to dig deep to overcome her fears, but her life gets more complicated through her spoken-for boss, Jonny.

Themes

Economic pressure shaping choices, Public competition as turning point, Mentorship enabling skill growth, Romantic entanglements complicate decisions, Social status expectations, Memory of trauma affecting performance

Available on

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

No Strings Attached

2. No Strings Attached

Comedy Romance Romantic Comedy Awkward Comedy
6.2
20111h 47min

Overview

Emma is a busy doctor who sets up a seemingly perfect arrangement when she offers her best friend Adam a relationship with one rule: No strings attached. But when a fling becomes a thing, can sex friends stay best friends?

Themes

Friendship boundaries in romance, Casual vs committed love, Jealousy and emotional risk, Misperception and trust in dating, Career life balance and dating, Family influence on relationships

Available on

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

What a Beautiful Day

3. What a Beautiful Day

Comedy Awkward Comedy
6.3
20111h 32min

Overview

Checco, an uneducated but self-satisfied fellow from Milan, who has always dreamed of becoming a police officer, fails his entrance exam for the third time. It must be said that at the oral examination Checco said that the reason why he wanted to join the police was benefits in kind and cronyism! But the young man has connections and he soon finds himself a security agent at the Milan Cathedral. Of course the bumbling idiot proves a living catastrophe! Spotted by Sufien, an Arab terrorist who is preparing an attack against the cathedral, Checco appears as the perfect sucker. To manipulate him, he sends his charming sister Farah to him, with the mission to seduce him...

Themes

Romance under pressure, Unintended consequences, Class ambition vs service, Dangerous alliances, Deception and masquerade, Loyalty versus manipulation

Available on

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

Toast

4. Toast

Drama Comedy History Family Family Drama
6.5
20101h 36min

Overview

Young Nigel Slater has big culinary aspirations, even though all his mother knows how to make is toast. When his mother dies, relations grow strained between Nigel and his father, especially when he remarries a woman who wins his heart with a lemon meringue pie. Nigel enters culinary school, starts working in a pub, and finds himself competing with his stepmother - both in the kitchen and for his father's attention.

Themes

Sexual awakening, Ambition and loyalty, Family dynamics under strain, Maternal influence through cooking, Remarriage and adjustment, Nostalgia and craft

Available on

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

Romantics Anonymous

5. Romantics Anonymous

Drama Comedy Romance Romantic Comedy Awkward Comedy
6.9
20101h 20min

Overview

What happens when a man and a woman share a common passion? They fall in love. And this is what happens to Jean-René, the boss of a small chocolate factory, and Angélique, a gifted chocolate maker he has just hired. What occurs when a highly emotional man meets a highly emotional woman? They fall in love, and this is what occurs to Jean-René and Angélique who share the same handicap. But being pathologically timid does not make things easy for them. So whether they will manage to get together, join their solitudes and live happily ever after is a guessing matter.

Themes

Collaboration under pressure, Craft as lifeblood, Social anxiety and romance, Fear of intimacy, Support networks and growth

Available on

Amazon Video
Plex Channel
Data provided by JustWatch.Availability may vary by region.

It's Kind of a Funny Story

6. It's Kind of a Funny Story

Comedy Drama Coming-of-Age Drama Awkward Comedy
7.1
20101h 42min

Overview

A clinically depressed teenager gets a new start after he checks himself into an adult psychiatric ward.

Themes

Coming of age, Academic pressure, Mental health care, Creative aspiration, Psychiatric ward, Peer friendship dynamics

Available on

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

Boy

7. Boy

Drama Comedy Coming-of-Age Drama Awkward Comedy
7.5
20101h 28min

Overview

Boy, an 11-year-old child and devout Michael Jackson fan who lives on the east coast of New Zealand in 1984, gets a chance to know his absentee criminal father, who has returned to find a bag of money he buried years ago.

Themes

Absent father impact, Family bonds under pressure, Economic desperation and crime, Anger and control, Male identity under strain, Youth coming of age

Available on

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

Diary of a Wimpy Kid

8. Diary of a Wimpy Kid

Comedy Family Awkward Comedy Parent-Child Family
6.2
20101h 32min

Overview

Greg Heffley is headed for big things, but first he has to survive the scariest, most humiliating experience of any kid’s life – middle school! That won’t be easy, considering he’s surrounded by hairy-freckled morons, wedgie-loving bullies and a moldy slice of cheese with nuclear cooties!

Themes

Peer pressure and conformity, Belonging and exclusion, Classroom social ladder, Identity within adolescence, Popularity through performance, Group dynamics and mischief

Available on

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

She's Out of My League

9. She's Out of My League

Romance Comedy Romantic Comedy Awkward Comedy
6.4
20101h 44min

Overview

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.

Themes

Insecurity and self-esteem, Appearance versus worth, Class difference in romance, Opposites attract dynamics, External judgment and doubt, Safety versus risk in romance

Available on

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

Leap Year

10. Leap Year

Romance Comedy Romantic Comedy Awkward Comedy
6.4
20101h 40min

Overview

When yet another anniversary passes without a marriage proposal from her boyfriend, Anna decides to take action. Aware of a Celtic tradition that allows women to pop the question on Feb. 29, she plans to follow her lover to Dublin and ask him to marry her. Fate has other plans, however, and Anna winds up on the other side of the Emerald Isle with handsome, but surly, Declan -- an Irishman who may just lead Anna down the road to true love.

Themes

Trust and vulnerability, Traditional expectations vs desire, Commitment under pressure, Cross-cultural misunderstandings, Chance encounters shaping choices, Fate vs planning

Available on

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