Halloween party
When I was a teenager I was extremely shy, which made any dealings with girls extremely difficult. I used to go to a men's hairdressers to get my haircut, where one of the hairdressers was a pretty young girl. On one occasion when I was about 15, in October, I was called to her chair.
I sat in the chair in petrified silence while she cut my hair, her body occasionally brushing against me. At one point she asked "Are you having a party?".

I decided that now was the time for me to get over my embarassment and to be cool. So I replied, "Yes I'm having a Halloween party, you can come if you want." I waited hopefully for her reply, already imagining my mates being impressed when this angel turned up at my party.

"No no, are you having a parting?", she said, more loudly.

"Oh yes, on the left, please," I stuttered before descending into even more petrified silence. I left the hairdressers with a lovely parting on the left, and never went back there again.
(Smale is stuffed, Fri 6 Nov 2015, 12:34, 1 reply)

In the 80s my brother in law idolised Freddie Mercury and dressed like him - looked like his twin brother.
Short haircut, moustache, white teeshirt, fitted leather jacket, studded belt, the works. There may even have been a leather biker cap with a chain. There were certainly cowboy boots.

He looked REALLY cool and everyone was impressed.

Of course, there was no internet back then so it took some years for us all to realise that the look was pure San Francisco gay clone. Heck, we lived in an English backwater, we didn't even know there WERE such people.

I bet he's hunted down all the photos and burned them.
(Juan Quar is clinging to her front teeth on, Fri 6 Nov 2015, 19:23, 2 replies)

Bathroom inspector
One day at (my former) work at an office block, I ventured into the cloakroom/changing room/toilet/shower room hybrid towards the front of the building. There was someone in there - no idea who he was, but he did look cool: business suit, neatly trimmed beard. He was obviously someone important, or at least someone who thought he was important.

Me being a friendly chap, I smiled at him. However, the look I got in return was one that (probably quite rightly) said "Don't you smile at me! Look at how cool and important I am! I wipe shit like you off my shoes every day! You disgust me!" - he waltzed importantly past me, then grasped the door handle to make a purposeful and important exit ...

... only, he didn't grasp the door handle to the door to exit, he accidentally grasped the adjacent door which led to the shower, which was about the size of a toilet cubicle. As his important momentum carried him into the tiny room and he realised he'd walked into a dead end, a moment of horror, humility and embarrassment wiped across his face ...

... until he realised how to rescue the situation. He took several important moments to look importantly around the tiny cubicle, nodding wisely throughout as though - of course - he'd deliberately gone into the shower room to see if it was up to his important standards. He then waltzed past me again and exited the cloak/changing rooms by the proper door.

I hope he heard me laughing as he marched importantly away.
(iwrite4u, Fri 6 Nov 2015, 14:59, 3 replies)

I was a cool hard biker
18 years ago a 16 year old me used to do my paper round on my Kawasaki AR50 which in case you don't know anything about motorbikes is the best motorbike ever produced, capable of around 200mph and way better than a fizzie.

Everyday I would whizz around the paper round deliver all my papers, yet on the ride home it would start to struggle and the engine would die. I could just about keep it running in first gear but only if I stepped of it and walked along side it and let it run on tick-over (any throttle and it just died). It never went wrong before or during the round and after I got home and got ready for school it was always fine again to ride to and from school only then break down again on my paper round the very next day.

This went on for so long that I eventually got so used to it that I could ride it home from my paper round standing on the left hand foot-peg, in first gear and still make pretty good time. But it remained a mystery until one day I was reading up on changing the jets on the carb and came across a section in my Haynes manual about the air intake. On the AR50 it was under the seat. Everyday after my paper round I would have to ride past the local secondary school who were bitter rivals to my own. In order to look like a cool biker and not a spotty 16 year old oik I would take my paperbag off and stuff it under my seat and in doing so blocked the air intake. Stepping off relieved the pressure just enough to let enough air in so it could run on tickover.

So instead of looking cool I got to push my bike past groups of jeering school kids, every day, for months.
( Peej, Fri 6 Nov 2015, 14:49, 1 reply)

Hats are cool
I went through a phase of wearing a black fedora hat, I thought it looked cool but was quite often mocked.
Standing at the bus stop, a group of teenagers on the other side of the road starting shouting comments about how silly my hat was.
Trying to appear cool and nonchalant I leaned against the glass pane, only there wasn't one there and I fell through the glassless frame to land in a heap in the gutter.
You can imagine the howls of laughter from the teens.
Luckily the bus arrived so i didn't have to cringe there for long.
(insomniac-surfer oh go on then, just this once, Fri 6 Nov 2015, 12:59, 11 replies)

( Two Hats 🎩🎩, Wed 11 Nov 2015, 16:56, 3 replies)

Westerns?
As an adolescent i always wanted a long leather duster coat. For me they were the epitome of cool but being skint they were always well out of my price range. I would have even gone for a cheaper canvas one but never found one to my liking. As i got older this vague yearning for the coat never actually went away but i didnt do anything about it either.
Then one fateful day i spotted a bloke selling them on a market stall for quite reasonable prices. I hurried over with my credit card clutched in my hot sticky little hands. Yes they had one that would fit so i quickly tried it on..
I looked in the mirror and realised with a sinking heart that it made me look an absolute tit. Dusters look great if you are tall and skinny with razor sharp cheek bones and piercing eyes. Not if you are an overweight pudgy bloke in his 30's.

I did wear a leather cowboy hat for a while though...
(andythepieman Is surfing the waves of indifference on, Sun 8 Nov 2015, 10:35, 10 replies)

wait a minute!
The topic here is 'tragic attempts at being cool'.

One word: emvee.
(dozers, do fuck off ur a nob m8, Fri 6 Nov 2015, 16:47, 13 replies)

( $$ ✅, Thu 12 Nov 2015, 20:32, Reply)

I found my first grey hair when I was 17 so spent the next ten years or so dyeing it
I thought this was the coolest shit ever at the time - undercut slightly grown out and dyed black and the top letterbox red with black streaks.

s4.b3ta.com/host/creative/20089/1447174983/coolhair.jpg

In retrospect, I look like I'm off to a rave with Mcbeef. This picture was taken in someone else's room, by the way, so I can't take credit/blame for the mid-90's posters either.
( emvee cruor deo cruoris, Tue 10 Nov 2015, 17:09, 10 replies)

Trying to stay down with the kids
I like to think I'm a relatively cool dad. However last week my teenage daughter and I were having a night in alone, in front of the TV. I put a picture of us cuddled up on the sofa onto Facebook.
I captioned it "Netflix and Chill"
Apparently, it means something different!
(sunray18, Fri 6 Nov 2015, 22:17, 5 replies)

HIGH SCHUNT.

( drimble he'd been white, he'd been black, Fri 6 Nov 2015, 18:19, 3 replies)

18, a gold paisley cravat
and a fucking pipe.
(riffjedibaby almost 1,000 chickens, Fri 13 Nov 2015, 10:26, 4 replies)

Hairdresser's revenge
I'd allowed my hair to become an amorphous blob of undecidedness, and couldn't really decide what I wanted to do with it. Looking back, it's probably always a bad idea to say to the hairdresser "Oh I don't know. Do what you want to it."

One flat top later, and I walked home feeling a little daft. The final straw came when I noticed that the shadow of my head was rectangular, and I hurried straight home and shaved it off before anyone saw me.

I did also persuade my neighbour to give himself a reverse mohican once. was quite amusing. He shaved that too after a day or so.

Nowadays I let my daughter cut my hair. She's not remotely qualified, but I quite like how it makes her cackle as she hacks chunks off, and I swear it looks better than any time I've let a hairdresser near it.
(teasus likes tea, Wed 11 Nov 2015, 3:45, 10 replies)

When I was a nipper, about 1979, I was given a pair of suede "HanSolo" boots.
I thought they were the coolest thing ever and couldnt wait to wear them to school. In the morning on my own front lawn I stood in a wet sticky fresh dogshit, and instead they stunk of shit all day and I got teased and never wore them again to school.
( cumquat may will not be commenting further on the allegations, Tue 10 Nov 2015, 21:34, 8 replies)

In my uni days I considered myself a junglist so wore a camo flak jacket and shaved my head.
I looked like I was about to commit a British reenactment of an American high school massacre.

I also once gave myself a hi-top ala Kid 'an Play. That was legitimately cool though.
( Slippery Mick ‏, Sat 7 Nov 2015, 14:29, Reply)

Sometime in the early 2000s I was working in an office in Central London
In time-honoured office tradition people would email round pictures and stuff that amused them and at the time, one frequent subject of general derision was the classic "business in the front, party in the back" mullet. Now I thought this was a bit lazy and obvious, so I sent round a new meme reading "Anyone can make fun of a mullet, but it takes a real man to grow one" before showing up to work with my brand-spanking-new hillbilly haircut.

For a few weeks all was great - I had terrible hair, people openly mocked it and the natural order of things was preserved. But then I started to notice more and more people around Soho and Shoreditch sporting similar dos and before long magazines were predicting the return of the mullet as being fashionable. Horrified at the thought that people would think that I might actually be trendy, I went to the barbers ASAP and had it cut off.
( emvee cruor deo cruoris, Fri 6 Nov 2015, 11:56, 2 replies)