Cheeky has 2 different meanings across 1 category:
Adjective
offensively bold
"a brash newcomer disputed the age-old rules for admission to the club"
"a nervy thing to say"
Impudent; impertinent; impertinently bold, often in a way that is regarded as endearing or amusing.
"The cheeky grin he gave the teacher after getting caught copying answers made everyone laugh instead of worry about his detention."