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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.
Will & Grace
Season 4
14
January 17, 2002
22 minutes
4.0/5
Brent Sexton
Prison Guard
Shelley Morrison
Rosario Salazar
Kirk Baltz
Glenn Gabriel
Cheryl Bricker
Sheila Slovinski
Steven Shaw
Judge
Bill Wrubel
Writer
James Burrows
Director