rolling deep

means when you are going out, playing out as some call it.

James:you rolling deep tommorow

Grayham: im already rolling deep with Becky, you can tag along too if you want?

by laaaaaaaaaaa August 27, 2009

rolling deep

When a group of friends get together in search of girls. It may be a place, like the mall, park, etc.

Yesterday we went rolling deep, but Lucas likes guys, so he was not rolling deep.
Edder brought some girls from the mall, he is rolling deep.
Sergio and Rene are talking to the hot girls, they are rolling deep.

by EdderA February 23, 2008

roll deep

Used to describe having sex with a fatty.

Last night I was so hard up I had to roll deep.

by Dave December 16, 2004

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

"what you know about rolling down in the deep end"

by ninjakirbz June 22, 2021

roll deep

Burning a hole in your jeans to prove you are true to your friends.

We are tight because we roll deep.

by ibp October 18, 2004

roll deeps

describes an especially nice pair of footware usually athletic shoes.

"Ey homey, dem kicks is tight."
"Wurd, dey my new Roll Deeps."

by Big Swol September 26, 2005

roll deep

When you going to stomp out some dudes
with some homees.
In how many cars you have going to the place to meet that are from your side.

"We were rollin 3 cars deep"

by jdub December 11, 2002