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Rolling down in the deep 

what you know about rollin down in the deep?
ass line from the ass song by Masked Wolf
A: My mother has sadly passed away from ligma
B: Whatchu know bout rolling down in the deep?

rolling down the windows 

The art of waving one's hands around in circles while gettin air in a sport like skateboarding or snowboarding.
Dude, you need to do some grabs when you're in the air...quit rolling down the windows!

rolling down in the deep end 

a lyric from "astronaut in the ocean", a 2019 song by that was released by masked wolf and gained popularity from tiktok when the song was re-released in 2021

Rolling down in the deep 

When 2 gay gamers try to have rough hard sex under water for at least 420 minutes+, and when the cum mixes with the water the other person drinks it up and vomits it out into the other persons mouth and then they drink it. After the other person drinks it, they have extreme diarrhea which they use as lubricant on their dicks. Then they take turn giving each other blowjobs.
Kevin: You want to try rolling down in the deep?
Albert: I've been waiting for you to ask that.

What you know about rolling down in the Deep? 

'What you know about rolling down in the Deep?' is a lyric from the hit hip-hop song 'Astronaut in the Deep' from Masked Wolf.

It is also used as a way of asking how your recent sexual intercourse went, for example:

cat rolling down the hill problem 

A physics problem involving a cat rolling down a hill. Commonly given when asked for physics answers.
"What's the answer to question 1?"
"What, the cat rolling down the hill problem?"