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1.
A combination of the words "Drinking" and "Chillin."
Monica Lewinski: Hey Bill! What are you doing tonight?

Bill Clinton: Not much, just drillin at the crib. If you come over I'll flick your bean.
by Saywhatwho? September 12, 2009
26 10
 
2.
Irrepressibly attractive; Sexier than real life; an attraction so intense it causes physical pain.
That girl is DRILLIN holes through my brain, man.
My shorty is drillin harder than a dentist.
Where's my snare? I'M DRILLIN hard.
by Pey Wei, Claireistotle September 21, 2010
10 7
 
3.
Slang for awsome
That ride was drillin'
by Mango hearer March 01, 2010
2 2