Awkward person playing charades (4,4)
I believe the answer is:
hard case
'awkward person' is the definition.
(term for a stubborn or tough person)
'playing charades' is the wordplay.
'playing' is an anagram indicator.
'charades' with letters rearranged gives 'HARD CASE'.
(Other definitions for hard case that I've seen before include "Tough guy" , "Brief problem, perhaps" , "Tough person to deal with" , "challenge to legal team?" , "Intractable person" .)