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This is a question Tragic Attempts at Being Cool

You say 'I'm cool, I'm no fool' but then you wind up dropping out of high school'. It was Melle Mel who said that, I swear down. THE Melle Mel, that's right.

This week's question is all about your tragic attempts to be cool (pictures welcome), or perhaps times when you've witnessed another's misguided attempt to be a hep-cat daddio. Share the shame, it might make you feel better.

(, Fri 6 Nov 2015, 10:50)
Pages: Popular, 2, 1

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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.
(, Fri 6 Nov 2015, 12:59, 11 replies)
fedoras are for Discworld IT autisms and paedophiles.

(, Fri 6 Nov 2015, 13:08, closed)
Whatever happened to vagabond?

(, Fri 6 Nov 2015, 13:10, closed)
He was convicted of a series of vicious sexual assaults and was brutally murdered in prison.

(, Fri 6 Nov 2015, 13:37, closed)
Wow! Friday's shaping up to be ever better than I imagined!

(, Fri 6 Nov 2015, 14:16, closed)
His girlfriend said "You're so fucking male!"

(, Fri 6 Nov 2015, 14:27, closed)
lol

(, Fri 6 Nov 2015, 14:40, closed)
uh huh

(, Fri 6 Nov 2015, 14:09, closed)
And then Trigger pulled a face.

(, Fri 6 Nov 2015, 15:36, closed)

this was way before
(, Fri 6 Nov 2015, 16:55, closed)
Was it an actual fedora or a trilby that you called a fedora?
goodmenproject.com/featured-content/brand-thats-not-a-fedora-and-stop-wearing-it/
(, Mon 9 Nov 2015, 1:07, closed)

definitely a fedora, a black one with a purple band
(, Mon 9 Nov 2015, 14:00, closed)

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Pages: Popular, 2, 1