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1.
diddy boppin refers to the "bop" and "swag" p diddy was walkin with when he beat his court case.
one cat: damn holmes how you gon be diddy boppin like that
second cat: word homie, i just copped some ice creams
by doseone December 31, 2007
 
2.
the act of trying to get into a club wearing your sweat pants. it doesn't matter if they have pockets your still not getting in.
bouncer: "Excuse me sir, I can't let you in, we don't allow sweatpants here."

unidentified male: "WHAT!?! BUT THEY HAVE POCKETS! YOU ARE JUST JEALOUS I AM DIDDY BOPPIN' TO THE FULLEST."

bouncer: "Please step aside sir."
by mugsbugs March 11, 2011
 
3.
smashing a large amount of hoes....
pimpin........balllin!!
I didn't know James got girls like that,that kid is diddy boppin.........
by Young Gravano December 23, 2006