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.