Episode 74 of "Will and Grace"
s04e03 Crouching Father, Hidden Husband

Jack is puffed up with paternal pride as he escorts his long-lost teenaged son Elliot to a junior high school dance but not before he coerces Grace into posing as Elliot's date – which only revives her own tortured memories of rejection from school dances many years before. Elsewhere, Karen has great fun at her lawyer Will's expense when she continues to capriciously summon him for bogus "emergencies" – that is, until she really needs him.