Will & Grace · S04E14

Grace in the Hole

2002-01-17 · 22 min · ★ 4.0 (1) · TMDB

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 â€" 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.