Being single, being detached from the relationship sphere. Flying solo, not getting any. Comes from St. Paul, a prominent theologian and opponent of sexual relations.
Friend 1:Hey, brah, how come you ain't got no hoes?
Friend 2:Nah, I'm St. Pauling it tonight.
or
Friend 1:Girl, you ain't had a man in months, what up?
Friend 2:St. Pauling it.