S4, E14: While visiting Karen's (Megan Mullally) incarcerated husband, Grace (Debra Messing) re-discovers a handsome high school friend (guest star Kirk Baltz) who's also doing time in prison, and despite Will's (Eric McCormack) advice, she's soon dressing up and visiting the inmate while dreaming of a life together outside the Big House. Conversely, a sympathetic Rosario (Shelley Morrison) chides Karen for not standing by her man - and bets her boozy boss that she and pal Jack (Sean Hayes) cannot stay penned-up together in the same room for three days without harming each other.