10 Most Uncomfortable Moments From The Inbetweeners

by : Julia Banim on : 18 Oct 2020 17:09
10 Most Uncomfortable Moments From The Inbetweeners10 Most Uncomfortable Moments From The InbetweenersE4

As much as many of us like to think we were cool young things back in the heady days of sixth form college, in reality most of us could be placed into four distinct categories: Will, Jay, Simon and Neil.

I was most definitely a Simon, with an overly romantic and dramatic side that still gives me the odd mortifying flashback at two in the morning.


Oh, and in true Simon fashion, I once threw up at a party in front of a lad I fancied, and managed to convince myself that he thought I was somehow very wild and unconventional. Reader, he did not.

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The Inbetweeeners was one of the funniest sitcoms of the noughties, and all too sharply captured what it actually felt like to be a teenager during these years.

This was a time when social media was just starting to creep into every aspect of our lives, when our mp3 players were jammed with the likes of Razorlight, The Libertines and The Kooks.


The smell of Lynx practically permeates through every scene, instantly taking me back to a long-departed time of Battle of the Bands, suburban house parties and electric blue WKD bottles.

But most of all, The Inbetweeners captures – more than any show before or since – the uncomfortable, icky embarrassment of being 17 and flailing about miserably in the hopes of meeting basic social expectations.

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And so, without further ado, here are the ultimate 10 most embarrassing moments from a programme that honestly only gets more awkward with every rewatch.


10. Neil punches a fish to death

Having never been the brightest of the bunch, Neil made up for his obliviousness somewhat with this gruesome show of strength.

It’s honestly quite difficult to think about embarrassing moments from Neil’s perspective, as I’m not entirely sure that he gets embarrassed.

Like a cheerful Labrador, Neil bounds through the show without seeming to feel the anguish the others do about not fitting in, or being generally quite repellent to girls.


But for sheer cringe factor, this gory mercy killing very much deserves a place on this list. Neil’s pained face as he solemnly pummels the still-writhing fish into mush makes for one of the grimmest moments in the series, and does nothing to improve the gang’s street cred.

You can watch the video below:

9. Jay propositions an elderly ice cream lady


Many of the biggest laughs in the show came from Jay’s graphic – and wildly exaggerated – reminiscences of his alleged sexual conquests.

From being dumped because his ‘c*ck was too big for her’, to partaking in a Caravan Club orgy, the would-be lothario’s imaginary exploits very much deserve a listicle of their own.

But the most toe-curling tale of all is undoubtedly the yarn Jay spins during The Field Trip, about the famed ‘Swanage MILF’ who ‘sucks schoolboys off’.

Instead of dedicating himself to the educational aspects of the trip, Jay predictably spends his time tracking down the mystery temptress, a search that ultimately leads him to an elderly – and extremely baffled – ice cream lady.


8. Will attempts to replace his missing pubes with a wig

Even in an episode that sees Jay masturbating to an old lady’s photo in a care home, this mortifying moment is a standout in the series.

The Duke of Edinburgh Awards sees a decidedly-less-than-experienced Will try to seduce older woman Daisy, who used to babysit him as a kid.

Unfortunately, Will’s attempts at proving his maturity are scuppered by Jay and Neil, who – in a cruel prank – pour hair removal cream down his pants, causing his pubes to fall out.

When things start to heat up with Daisy, a panicked Will ends up stuffing an elderly woman’s wig down his trousers. This turns out to be an only marginally better idea than Simon’s suggestion that he simply draw them back on with marker pen.


7. Neil gets thrown out of a club after acting suspiciously

With A Night Out In London, we weren’t exactly expecting the boys to have a normal one. This episode brought us Simon’s p*ss-soaked shoes and the iconic ‘bus w*nkers’ line, and it was clear the evening was headed for disaster from the moment Neil peed into a can during the car journey up.

In one of the most wince-inducing injuries of the show, Neil ends up cutting his ‘helmet’ with the sharp bit of the can, a mishap that ultimately results in him being booted from the club.

While inspecting his wound in the loos, clubbers get the wrong end of the stick and report him to security, bringing the big night out to an abrupt and deeply embarrassing end.

You can watch Neil take that fateful p*ss for yourself below:

6. Jay makes a ‘friieeeeeennnd!’

Jay’s insecurities make up one of the recurring themes of the show, and it’s clear that a fair bit of sensitivity runs beneath his crude bravado.

In Will Gets a Girlfriend, we see Jay blow up in spectacular fashion after a bit too much teasing from his mates.

After catching up with an old friend he (allegedly) had trials for West Ham with, the other boys take gleeful delight in mocking Jay with thumbs-up gestures and the oft-quoted refrain, ‘Friieeeeeennnd!’

Jay gets increasingly agitated by the ribbing, until his frustrations eventually boil over. Before the episode’s out, we find him jumping up and down on his ‘football friend’s’ car in a fit of rage, yelling, ‘I’m not your f*cking friend, alright?!’

You can watch Jay explode in the following clip:

5. When Simon throws up over Carli’s brother

Simon has been in love with Carli D’Amato since he was eight years old, and in this episode we feel every agonising, unrequited pang of it.

Bunk Off is only the second episode of the series, but it’s one of the most memorable, with the pals skipping school and getting absolutely sozzled on Beefeater Gin and crisps.

Pumped up with confidence from the drink, Simon decides – wrongly – that it’s time to declare his love for Carli, which he does so in a fairly bold fashion, spray-painting words of adoration all over her driveway.

Feeling sympathetic after Simon’s friends laugh at him, Carli invites him over to hers that very evening, and – even though we know all too well that it won’t – we have our fingers crossed that he’ll be able to smooth things over.

Instead, the evening goes even worse than anyone could have feared, with Simon unleashing a volcanic torrent of boozy vomit all over Carli’s little brother.

It’s probably best to wait to watch the following clip until after you’ve had your tea:

4. Jay joins ‘The Dead Hand Gang’.

This one cracks me up every time, mainly because of how fantastically daft the name of the ‘gang’ is, and how proud Jay is to be affiliated with it.

In Will’s Birthday, we see Jay boast that his mate’s brother invented the ‘Sleeping Beauty’, a masturbation method whereby you sit on your hand for a bit until it goes numb, making it feels as though someone else is touching you.

We later see this technique in action, with Jay desperately trying to close his laptop with his floppy, dead hand after his mum and Neil interrupt. His unconvincing cries of, ‘It’s just a film! A normal film!’ still crack me up.

You can learn more about this top secret society in the following clip:

3. Will eats drugs and then asks for his mum

Will is no stranger to public humiliation, but this is a horrifyingly awkward moment even for the famed ‘Speccy Kid Who Sh*t Himself’.

As with many episodes of The Inbetweeners, the action is sparked by the gang attempting to enact some sort of poorly-thought-out plan – in this case scoring weed and going to a gig – to boost their lowly social standing and ultimately attract girls.

Known as the more sensible one of the group – or the most boring if you ask his mum – Will is occasionally driven to prove himself to be less of a stick-up-the-bum than his briefcase would suggest.

In this instance, Will ends up getting so wound up by Jay about not smoking weed that he ends up actually scoffing it down like a bar snack.

Unsurprisingly, Will experiences some unpleasant and scary side effects that result in him dashing on stage, pleading with someone to get him ‘an ambulance, or failing that, my mummy’. It really doesn’t get any more toe-curling than that.

You can watch the most awkward gig announcement in television history for yourself below:

2. Simon tries and fails to lose his virginity during a trip to Warwick

I find this one almost impossible to watch, being an excruciating reminder of just how weird and humiliating the early days of adolescent bonking can be.

We see the gang head up to Warwick University – famously Will’s last UCAS choice – to stay with Simon’s girlfriend Tara’s older sister, Sophie. The main purpose of the trip is for Simon and Tara to lose their respective virginities to each other, a prospect that Sophie is less than enthusiastic about.

Things begin awkwardly and proceed to go downhill fast, with Simon making the fatal mistake of accepting sex advice from Jay.

After giving himself a ‘tactical’ pre-sex w*nk, Simon is horrified to find that he can’t get an erection and ends up slapping and screaming at his own penis.

The episode culminates with Simon inadvertently flashing everyone in the student flat share, and Sophie threatening to call the police. During my rewatch, I honestly peeked at the final scenes through my fingers as if I was watching a particularly bloody horror film.

See if you can stomach the following clip:

1. Of course, it could only be the bit where Will sh*ts himself in an exam

Poor Will didn’t exactly have an easy transition from posh private schoolboy to the ‘briefcase w*nker’ of Rudge Park Comprehensive.

Unfortunately, any hopes of fitting in were eternally dashed after he ends up audibly sh*tting himself during his AS Politics exam.

In this episode, Will’s studious nature ultimately becomes his downfall, with his choice of energy drinks over a good night’s sleep causing his stomach to betray him.

There’s a fine line between comedy and tragedy, and there is honestly nothing more harrowing to me than the thought of cr*pping my pants as an awkward 17-year-old sitting an exam.

Will’s mournful pleas of, ‘I thought it was a fart sir, I thought it was safe!’ as Mr Gilbert leads him waddling from the exam hall will haunt me forever. As Will himself admits while carrying his poo-covered school trousers into the pub, ‘There’s no coming back from that.’

You can watch the most embarrassing moment of The Inbetweeners – and potentially in comic history –  below:

It’s been 10 years since the show ended, and no other comedy since has made me cringe in quite the same way.

A generation-defining sitcom for anyone who has ever had to suffer the embarrassment of being a British teenager, The Inbetweeners still very much holds up as a show that keeps you laughing even as you’re gasping in horror.

You can revisit the BAFTA award-winning comedy series on All 4 now.

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Julia Banim

Jules studied English Literature with Creative Writing at Lancaster University before earning her masters in International Relations at Leiden University in The Netherlands (Hoi!). She then trained as a journalist through News Associates in Manchester. Jules has previously worked as a mental health blogger, copywriter and freelancer for various publications.

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