Jump to Main ContentJump to Primary Navigation
Top

The 11 most awkward moments in film

something about mary.jpg
apie.jpg
615x330_bridesmaids.jpg
virgin pic.jpg

In real, living, breathing life, having an awkward moment with someone is something we try to avoid. That water-cooler small talk, that unbearable silence in the lift or meeting your other half's parents for the first time - all painful to experience.

But in movies, we tend to get a kick out of them. Sure, we'll squirm in our seats and maybe we'll even watch through our sweaty fingers but at least we're not in the situation. So here are 11 scenes where you can live an awkward moment vicariously through someone else. Try to enjoy.

(Images: Rex Features, All Star)

Swingers - the voicemails

Before the days of the cowardly text, actually talking on the phone was an inescapably important element to dating. Which meant that the cruel mistress that is the answering machine was a necessary evil. In this increasingly hard-to-watch scene from Swingers, Jon Favreau's attempt to leave a casual message for a woman he's just met is an unmitigated disaster where each attempt is even worse than before. Her ultimate reaction is totally justified.

Bridesmaids - the engagement party speeches

Most of Bridesmaids revolves around uncomfortable humour, thanks to Annie, a heroine whose default mode is awkward. It's showcased best in this series of ultra competitive speeches at her best friend's engagement party. As she tries to outdo her rival bridesmaid, Annie wades through new depths of awkwardness culminating in the world's least appropriate singalong.


There's Something About Mary - the bathroom

Now, if we actually had prom over here then we're sure it would be a hugely awkward experience. It's possible that our view is a bit tainted by this 1998 gross-0ut comedy however. In the opening sequence, Ben Stiller's character finds himself in a slippery slope of awkwardness after he goes for a seemingly innocent trip to the bathroom. But things soon get cocked up. So to speak.

American Pie - the tube sock

Taking a situation that would make anyone crave the ability to disappear, this memorable opening to the first American Pie film sees our hero Jim get interrupted while, ahem, enjoying himself. By his mum. And then his dad. Yes earth, you can cave in and swallow him now.

Taxi Driver - the blue cinema

Deciding on where to take a first date is a vastly underestimated process. You want to showcase somewhere that you're familiar with but a slight element of ambition and effort is also necessary. To be fair to Travis Bickle, he gave it his best. But, unsurprisingly, his choice of an XXX cinema didn't go down so well with the more refined Betsy. Easily the worst first movie date ever.



Meet The Parents - Milking cats

Ben Stiller crops up again in a situation that was always going to be fraught with awkwardness: meeting the parents. It's a rite of passage that's made even more difficult with De Niro playing dad. In this dinner scene, Stiller is forced to go down a trail of increasingly absurd lies involving the milking of a cat. It somehow gets worse...

Goodfellas - a funny guy

A mixture of awkwardness and a genuine terror, this iconic scene sees Ray Liotta telling Joe Pesci that he's "a funny guy", which, given the jokes that he's just been telling, seems like an understandable observation. But in a brilliantly controlled piece of acting, Pesci takes the comment a little bit badly...

Wedding Crashers - the dinner table

A formal dinner with new people is always ripe for embarrassment. Said set-up is made even more excruciating when you're trying to hide the fact that you're being, ahem, played with under the table. Vince Vaughn tries his damn best though. So there is that.

About A Boy - Killing Me Softly

Kids are mean little beasts. We're still able to remember what it was like being around them on a daily basis. At school obviously. So performing a song in front of an entire hall of them has never been very high up on our to-do list. This decision was proved to be a good one after we watched, and cringed, at Hugh Grant's attempt to save the day in About A Boy. Well done us.

The 40-Year-Old Virgin - poker talk

Trying to feign convincing locker room chat with "the lads" when you have zero sexual experience is not going to be easy. So this scene where Steve Carell tries to persuade the guys that he's a ladies' man is difficult to watch. Never refer to a breast as feeling like a bag of sand. Good to know for the future.

Superbad - the punch

When you're around a girl you're trying to impress, mind where your hands accidentally end up swinging. That's all we're saying.

Related

superbad.jpg

Most awkward high school moments in film

affleck-kerry.jpg

Most awkward celebrity handshakes

zooey.jpg

30 movie girls who'll break your heart

hero_filmposters.jpg

50 Craziest B-Movies

virgin.jpg

Judd Apatow's funniest moments

apatow wisdom hero.jpg

20 pieces of wisdom from Apatow movies

Comments

More

Why Rocky is the most important film about masculinity ever made

As the film turns 40, here's why the boxing saga is so much more than an underdog story

by Tom Fordy
01 Dec 2016

We asked men to tell us which movies make them cry

...and then we definitively ranked their pain

by Sam Diss
30 Nov 2016

Watch newly released trailer for Star Wars: Rogue One

by Joe Ellison
28 Nov 2016

Adam Driver and Andrew Garfield spent a week in silence in Wales

Solid dedication to a film's title

by Emily Badiozzaman
25 Nov 2016

Watch boxing drama Bleed For This for FREE with ShortList Film Club

Another, erm, knockout offer from our Film Club

by Tom Fordy
23 Nov 2016

Danny Boyle tells us what to expect from Trainspotting 2

Danny Boyle on why he’s brought back four icons for T2: Trainspotting

23 Nov 2016

Watch the trailer for Martin Scorsese's epic 'Silence'

30 years in the making: here's your first look

by Dave Fawbert
23 Nov 2016

Watch the full trailer for Netflix's Barack Obama biopic

From Beta House to The White House

by Joe Ellison
22 Nov 2016

20 best thrillers to watch on Netflix

How many of these nerve-janglers have you seen?

by Tom Fordy
18 Nov 2016

Ryan Reynolds discusses his nervous breakdown

"I literally had the shakes."

17 Nov 2016