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When a group of poople are walking or chilling together. Usually described for gang members. When people are rolling deep YOU DO NOT MESS WIT EM OR YOU WILL GET YOUR ASS BEAT.
Hater1: I thought you said you were gonna jump the Prince. I knew you were full of it.
Hater2: Nah i came with my clique but they punked out when they saw his crew.
Hater1: WHy? He was rolling deep?
Hater 2: Hell yea! at least 15 of em kats. We couldnt get near um.
Hater1: You pussy.
by prince ingus April 05, 2005
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Going out with several people, greater than 2. The term is used as a verb and accompanied with the number of people you are with.
Dude, we are rolling deep tonight.
by Ji Crew October 11, 2007
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1. You will know it when your doing it.
2. The act of being bad ass.
When you are cruzing 130 on the highway, you think you are rolling deep. Then when that guy passes you on the inside lane HE IS ROLLING DEEP.
by j-stubbs January 06, 2011
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5
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
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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
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