Jack, for one, may woo a wit! (5,4)
I believe the answer is:
court card
'jack for one' is the definition.
(jack is a kind of court card)
'woo a wit' is the wordplay.
'woo' becomes 'court' (synonyms).
'a wit' becomes 'card' (synonyms).
'court'+'card'='COURT-CARD'
'may' is the link.
(Other definitions for court card that I've seen before include "king, perhaps" , "King, queen or jack" , "Elevated club, maybe" , "King or queen, say" , "Jack or a queen, for instance" .)