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cooler than the other side of my pillow 

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!

Give My Pillow Some Head 

Shaniqua: I'm gon' give my pillow some head.
Terrell: Give yo pillah sum 'ed? Shit... you cheat'n on me?
Shaniqua: HELL NO! It's 3am, sheeeeee....
Terrell: Ah. Aight den. Peace.

Wiggle my pillow

ā€œwiggle my pillow I’m thirstyā€
Wiggle my pillow by Jfsc November 4, 2018

linger on my pillow 

dayyyum girl... why you gotta linger on my pillow?
linger on my pillow by smack!! July 18, 2004

Slapping high fives with my pillow 

Going to bed with palm rested on pillow.

While at the same time you're consequently giving the pillow a high five all night long!
I am so exhausted! Tonight, I will be slapping high fives with my pillow!

MrPillow5 

A streamer who gives robux in his live streams.
A: Hey did you see the MrPillow5's discord server?
B: Yeah, Its full of stupid memes.
MrPillow5 by anonymous April 24, 2021