Will & Grace (1998)

Season 3: Episode 5

Grace has made up her mind to break up with Ben because she's convinced their relationship is going nowhere -- but his charm and refusal to call it quits tempt her to reconsider. Meanwhile, Jack's latest and most outrageous cabaret gig is an absolute bomb until he frantically works an unwilling Will into the act by mercilessly ridiculing his attending friend's most-private confessions.