Initially an older man with maybe a younger woman (3)
I believe the answer is:
oap
'a younger woman' is the definition.
I know nothing about this answer so I can't tell whether this works.
'initially an older man with maybe' is the wordplay.
'initially' says to take the initial letters.
'man' becomes 'p' (abbreviation for pawn, a chess piece or 'man').
'with' says to put letters next to each other.
'maybe' becomes 'a' (I am not sure about this - if you are sure you should give a lot more credence to this answer).
The first letter of 'older' is 'o'.
'p' after 'a' is 'ap'.
'o'+'ap'='OAP'
Can you help me to learn more?
(Another definition for oap that I've seen is " senior citizen".)