(1) A pain in the ass.
(2) A real character.
(3) Someone who tends to be difficult, but still likeable.
(1) Boy that postal worker was rudely sarcastic - a real fucking pip.
(2) That guy over there is being overly friendly to everyone, asking them all sorts of questions, and just being too social in a weird way. Seems like a real pip.
(3) My wife was acting like a real pip last night, but of course, I still love her.
Prices shown in USD.