Gentleman worked with Net or Web (12)
I believe the answer is:
entanglement
'web' is the definition.
(synonyms)
'gentleman worked with net' is the wordplay.
'worked with' is an anagram indicator.
'gentleman' anagrammed with 'net' can make 'ENTANGLEMENT'.
'or' is the link.
(Other definitions for entanglement that I've seen before include "A complication" , "Imbroglio" , "Ill-advised liaison" , "Confused state; perplexity" .)