Will & Grace (1998)

S4E14 Grace In The Hole

During a visit to Karen's husband in prison, Grace unexpectedly reconnects with a charming high school friend who is also serving time. Ignoring Will's warnings, she finds herself dressing up for visits and fantasizing about a future with him beyond the prison walls. Meanwhile, a concerned Rosario scolds Karen for not supporting her husband and wagers with her tipsy boss that she and Jack can endure three days locked in a room together without clashing.