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sadboy season 

Lengthy periods of sadness and loneliness for sad boys
You good bruh?
Yeah, it's just sadboy season
sadboy season by Tokyo tommy March 19, 2018

sadboyprolific

man he’s the best rapper ever tbh, if you’re ever in your feelz u could def listen to him. or tbh any mood. he has amazing vocals and is really relatable. he’s really underrated and needs more hype tbh! so if ur reading def go listen to his songs specifically isho or alone
J-“ man have you heard of sadboyprolific”
M-“ nah bruh who is that?”
J-“ only the best rapper ever, go check out isho by him you won’t regret it”
M-“ight man, damn he’s amazing everyone should hear this!”
J-“ik man”

SadBoy Rxy 

That new Sadboy Rxy made me cry ong.
SadBoy Rxy by David_kinoko October 9, 2021

sadboysinner 

Someone that is very depressed and wares his heart on his sleeve
Wow that guy is super depressed they must call him sadboysinner
sadboysinner by SADBOY October 17, 2020
/sad•boi/
noun
1. a boy who listens to Sasha Sloan
"He's definitely a sadboy. I heard him humming Lie."
sadboy by Silent Rice October 21, 2020
A sadboy or a sodftboi (softboy) is a person (usually in their teens 13-19) who cries about their problems instead of fixing them.
You rarely see one, because they lack social interaction and rarely go outside their own homes.

In case you haven't, here's what they look like: They will usually wear informal clothing, like an oversized hoodie, hoodie without hood, hoodie without zipper... Etc. The type of music they listen to is a form of music that is catchy to listen to, but you wouldn't be caught dead doing so; a mix of ukulele and sad singing and more recently, sad rap.
They often times spend their time on the popular messaging app discord, mostly going on socialization and dating servers. They spend their time in the voice rooms the server provides, often times faking panic attacks and speaking with a tired monotone. Strangely enough, they will be in a relationship with somebody, but since they don't socialize very often, 9 times out of 10, it's online (On the aforementioned app Discord).
A more ancient equivalent to the "sadboy" is the emo, and in many ways they're similar, but the "sadboy" is a more modern take.
"Hey call Jacob, he might hang out with us!"
"He says he can't, he is something called a "sadboy" "
Sadboy by Fuckshitassdick February 21, 2021