Will & Grace

Grace in the Hole (4x14)

Air date: Jan 17, 2002

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.