Will & Grace (1998)

S4E25 A Buncha White Chicks Sittin' Around Talkin'

Will is taken aback by his own feelings as he senses his "biological clock" ticking, leading him to surprise Grace with a proposal to be the mother of his child. However, during their therapy session, Grace expresses her concerns about the sacrifices that come with such a decision, culminating in a shocking confession. Meanwhile, motivated by Will's determination to embrace life, Jack decides to audition for a real Broadway show, while Karen prepares for an uncomfortable visit with her incarcerated husband for a long-awaited conjugal meeting.