Issue with old lady getting with new boyfriend (5,3)
I believe the answer is:
young man
'boyfriend' is the definition.
('young man' can mean someone's boyfriend)
'issue with old lady getting with new' is the wordplay.
'issue' becomes 'young' (I've seen this before).
'with' says to put letters next to each other.
'old lady' becomes 'ma' (both can mean mother).
'getting with' is a charade indicator (letters next to each other).
'new' becomes 'n' (common abbreviation eg NT for New Testament).
'young'+'ma'+'n'='YOUNG MAN'
(Other definitions for young man that I've seen before include "Youth" , "sweetheart" , "Old codger? Quite the opposite" , "Boyfriend - teenager" .)