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This is Westcountry slang dating back to before the First World War. Skates are very slippery fish and the name was applied to people who had slippery natures in that they were untrustworthy, would try to avoid giving information or were just not very likeable. The use of the name expanded to include people who were wheeler dealers or people who do a lot of ducking and diving but no actual work. The name is disparaging but at the same time may hold just a hint of reluctant admiration. It is, however, a warning as a skate has no conscience and is totally unscrupulous and untrustworthy. The term is believed to have been used extensively by the British armed forces and was used to describe someone who was a slippery customer, fishy and who avoided their share of the work.
"Watch yourself with him, he's a bit of a skate."
Skate by AKACroatalin April 19, 2015

Skateboard 

The good ol' plank o' wood. A skateboard is NOT a toy; it's a part of your fucking life, bro. Cruise to school, bomb hills, haul ass, eat shit, and learn a thing or two from and on your board. A skateboard has always been there. Get on and forget all the bullshit; enjoy the ride. You CANNOT use a skateboard as a fashion sense; if you do, you're a shithead. Thrash everything in sight and ride until you die.
Fuck doing homework. I have my skateboard.
Fuck doing drugs. I have my skateboard.

Fuck all this bullshit. I have my skateboard.
Skateboard by Fuck Love, Snort Drugs December 15, 2012

Skateboarding 

Stereo types aside, it's just a thing that some people like doing. Frowned upon by cops, business owners, and midle aged rich stuck up Bitchy women. You get kicked out of anywhere you can think off by just skating flatground.
HEY! THERES NO SKATEBOARDING HERE. YOUR DAMAGING THAT LEDGE!!!

But, we're skating flatground, though.

THATS IT, I'M CALLING THE POLICE!
Skateboarding by 75283skate March 24, 2011

Freeline Skates

Two separate aluminum skates for each foot with s-shaped trucks and a type of longboard wheels with less, but just enough grip. The skater is only held by the skate's grip tape and no straps.

Common reactions are:
"Whoa"
"Wow"
"How the f*ck can you do that?"
"How do you balance on that?"
"Is that like a ripstik?"
"Can I try?"
"Why is your skateboard cut in half?"

Freeline skaters usually have good looks, big shlongs, and an amazing personality.
I just saw a good looking guy who probably has a big shlong on a metal skateboard that was cut in half. He must've been on Freeline Skates!
Freeline Skates by Pwickle January 12, 2012

skaterfuck 

A combination of a fuckboy and a skaterboy
Alternatively, a very accident prone skateboarder
Marii:Whoa! Leah had such a bad fall off the skateboard! Dude she is such a skaterfuck

Leah: I’m to awkward to be a fuckboy and I’m too clumsy to be a skater boy, I guess I’m a skaterfuck
skaterfuck by Ranedrøp July 1, 2020

Tony Hawk's Pro Skater 

An adjective used to emphasize high achievement in any professional field.
Kassie: Mick, I got the job!

Mick: Tony Hawk's Pro Skater!

Kassie: All you care about is video games.

Mick: Nah, babe! It's Tony Hawk's Pro Skater that you got the job!