Cane applied to boy’s rear? That could be awkward (6)
I believe the answer is:
sticky
'awkward' is the definition.
(synonyms)
'cane applied to boy's rear?' is the wordplay.
'cane' becomes 'stick' (I've seen this before).
'applied to' is a charade indicator (letters next to each other).
'rear?' says to take the final letters (I've seen 'rear of' mean this).
The final letter of 'boy' is 'y'.
'stick'+'y'='STICKY'
'that could be' is the link.
(Other definitions for sticky that I've seen before include "Viscous - problematic" , "Oppressive" , "Awkward; tacky" , "Adhesive, gluey" , "Adhesive; awkward" .)