Will & Grace (1998)

Episode Overview

In a clever scheme to secure a night off from his job at Barney's department store, Jack hatches a plan to play matchmaker, exploiting his nerdy female supervisor's crush on Will. He knows about Will's dream of being a model for the store's catalogue and cleverly turns their shared interests into a "date," all while Will remains blissfully unaware of her true motives. Meanwhile, Grace ventures into dangerous territory as she compares her past sexual encounters with those of her boyfriend Nathan, risking their relationship.