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This shit is the most sexual thing a woman (besides a mother) could ever say to you, it literally means she wants to suck the fuck outta you’re dick.
Oh John you’re such a silly boy! (Oh John, I wanna suck your dick!)
silly boy by VOIDYT May 28, 2018

Silly Goose 

A word you use when you see your girlfriend in a very hot and spicy valentines outfit.
"yeah, yeah, yeah. You silly goose. You're so silly"
Silly Goose by shawtyslayer March 5, 2021

silly people 

Used to describe a class of black people that are loud, kool aid drinking, straw sipping, popeyes chicken eating, nacho cheese consuming, cell phone music blaring, shirt down to your knees wearing, movie talking, leprchaun hunting, public transportation dependant, excessively ghettofied black people.

Also used to describe a group of many sillies.
Look at all those silly people loitering aroung the ATM in the movie theater lobby.

Look at that group of sillies eating fried chicken.

"Detroit, Oakland, St.Louis, and Atlanta are the 4 silliest cities in America."

"did you see the silly on that bus?"
its when men, like my brother, are in love wit a nasty ass bitch and they know it but decide that its okay and continue to have a relationship wit her.
where silly hoe at, prolly wit that nasty ass bitch
Silly Hoe by Lavarr Barnett September 12, 2004

silly billy 

An proclaimation of victory used by someone at least 25 years older than their opponent. It is such a bad insult, that only the older (or should I say wiser? Maybe not...) can use it and not look stupid. It basically means that their opponent is too immature to be treated to a real insult.
Silly Billy, don't fuck wit dees old ass niggaz.
silly billy by Gumba Gumba March 5, 2004

silly dilly willie nelson style 

the act of ending any phrase or comment with "silly dilly willie nelson style"
Jizzon: You guys ready to play some golf.

Peezy: Oh for sure. I'm gonna slap them, "silly dilly willie nelson style."