Guide essentially ineptly separating female and male on road (8)
I believe the answer is:
shepherd
'guide' is the definition.
(I've seen this before)
'separating female and male on road' is the wordplay.
'separating female' becomes 'shep' (I am not sure about this - if you are sure you should believe this answer much more).
'and' is a charade indicator (letters next to each other).
'male' becomes 'he' (he refers to a man).
'on' means one lot of letters go next to another (in a down clue, letters appear on others).
'road' becomes 'rd' (abbreviation).
'shep'+'he'+'rd'='SHEPHERD'
'essentially ineptly' acts as a link.
This may not be right. Some or all of it may belong to another bit of the clue.
Can you help me to learn more?
(Other definitions for shepherd that I've seen before include "Pastoral worker with crook" , "marshal" , "Pastor" , "Keeper of sheep and goats" , "Animal tender" .)