Sharp, hurt (5)
I believe the answer is:
smart
I believe this is a double definition.
'sharp' is the first definition.
(I've seen this before)
'hurt' is the second definition.
('smart' can be a synonym of 'hurt')
(Other definitions for smart that I've seen before include "well-kept" , "Bright or dapper" , "Sting - witty" , "Posh" , "Intelligent; clean, tidy" .)