Episode 85 of "Will and Grace"
s04e14 Grace in the Hole
Title: Grace in the Hole
Original Air Date: 01/17/2002 on NBC
Plot Outline:
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.
