jerking off into the buttcrack of a pale white male, and then sliding your dick in between the asscheeks to simulate a bob sled run.
hey pale white man, remember when i jerked off into your buttcheeks and then stuck my dick in there to simulate a bob sled run? that was a great alaskan bob sled pillow sandwich.
by tim "fuckface" roy April 20, 2006
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A phrase used to imply that someone is really cool, awesome, and amazing. This person is pro at life. He/She usually has a long list of talents, but is often known for one specifically. When a person uses this phrase to describe themself, they are a fag.

This phrase stems from the fact that on hot summer nights, people often flip their pillow over on to the other side because it is cooler since their body heat has not worn off onto that side.
Kyle got lucky and swished a shot from half court and /thought/ he was cooler than the other side of a pillow. Shawn however drains half court shots constantly and we all knew that it was Shawn who was really cooler than the other side of a pillow.

(I have written more definitions under the name "I listen to Indie Music")
by Carrera's Wedge March 25, 2007
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Something that is cool, neat, or nifty.

Ever notice how when you sleep with a pillow, that if your neck gets hot you can just flip your pillow over and the other side feels cooler than the side you were previously laying on?
Wow I really like that new tractor you got there, Bob! That thing is cooler than the other side of my pillow!
by stuff-i-learnt July 24, 2006
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the 29th of May is the national put your pillow in your fridge day. So put your pillow in your fridge!
Hey dude, are you putting your pillow in your fridge on National Put your pillow in your fridge day? It's the 29th of May
by Calypso Valdez Caleo! May 28, 2018
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a terrifying insult, only chosen ones can use it
Dude, i hope both sides of your pillows are warm
by Krenarc October 07, 2021
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