In Henry James’ “The Ambassadors,” a literary journal editor from Massachusetts is sent by his benefactor and fiance to Paris charged with forcing her wayward son to break with his Paris paramour and bring him back to assume his place at the helm of the family advertising firm. His rediscovery of the cultural and artistic beauty in Paris, and his acquaintance with the son’s elegant but vulnerable lover offers him the opportunity to redeem his pledge as a young man to forge “a connection with higher culture”. This article explores James’ use of paradoxical negative constructions to communicate Strether’s psychological suspense as he tries to maintain the trust of his fiance while dealing honorably with the son’s lover.