Will & Grace (1998)

S3E5 Grace 0, Jack 2000

Grace has decided to end her relationship with Ben, convinced that they aren't heading anywhere. However, his charisma and determination to keep things going make her second-guess her choice. At the same time, Jack's latest cabaret performance is a disaster until he desperately pulls Will into the show, comically mocking his friend's most intimate secrets in front of an audience.