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Will & Grace Season 4 Episode 14

While visiting Karen’s incarcerated husband, Grace re-discovers a handsome high school friend who’s also doing time in prison, and despite Will’s advice, she’s soon dressing up and visiting the inmate while dreaming of a life together outside the Big House. Conversely, a sympathetic Rosario chides Karen for not standing by her man – and bets her boozy boss that she and pal Jack cannot stay penned-up together in the same room for three days without harming each other.

Episode Title: Grace In The Hole

Air Date: 2002-01-17

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