Graduate’s with the Italian guy (5)
I believe the answer is:
basil
'guy' is the definition.
(Basil is a man's name)
'graduate's with the italian' is the wordplay.
'graduate's' becomes 'bas'.
'with' says to put letters next to each other.
'the italian' becomes 'il' (the in Italian).
'bas'+'il'='BASIL'
(Other definitions for basil that I've seen before include "serially chaotic character" , "Doctor of the fourth century" , "Boy - herb" , "Fellow" , "Culinary plant" .)