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Sad boy season

The period over Christmas and new year when all the random boys from your past reach out to you. They’re still single and their loneliness is at its peak.

Example text “ Maybe I thought I'd say hi after many years. Xo”
“Hey it’s been way too long between messaging but how have you been?”
Have you been getting lots of randoms texts lately? Yeah it’s sad boy season.
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Sad Boy Season

The very moment summer leaves fall to the ground, and that first crispy cold wind hits your face. The exact instance that you consider the transition of Summer or Fall.
The music hits a little harder during Sad Boy Season
Sad Boy Season by LordVegeta420 September 5, 2022

Secret Sad Boy 

The act of using your own tears as lube while jerking off to pictures of girls who turned you down.
Yeah he spends alot of his time in his room being a secret sad boy.
Secret Sad Boy by Ranchgirls December 8, 2020

a bad but sad boy 

Used to define blond witches with daddy issues. Usually has some sort of trauma related to parental figures, and is a suicidal bitch. Does not have any friends and needs therapy.
She called him, and these are her words, “a bad but sad boy

fat sad boy 

Someone who just eats all the time everyday and never excersises or does shit about it. That also listens sad, suicidal or mental ill hip-hop songs and typically wears black or just plain colored clothes everyday and usually feels alone and like being alone and feeling depressed
fat sad boy by Fat Sad Boy January 24, 2018

sad drunk boy poem 

An angsty sad poem which is badly written because the poet/author was a drunk 20-sum year old boy who got his heart broken in a melodramatic way and is unable to cope with simple life problems, and that of which is what his poems reflect
*In English Class*
"What kind of stuff does Eddy write?"

"Oh, He only writes Sad Drunk Boy poems."

The Sad Boys 

A group of 6 high school boys who call each other gay and play tag every year for a whole month. The group normally consist of an Alpha male, A super chill Homie, A kid that always makes bad movie references, 2 beaners, and a semi beaner.
the Sad Boys act like retards when they’re all together
The Sad Boys by Geekypuss05 August 3, 2019