In "Twenty-Five Little Pre-pubers" from season one of Two and a Half Men , Charlie's attempt to charm Jake's teacher, Miss Pasternak, to avoid trouble backfires when she becomes overly intense, forcing him to find a way out of the relationship. Meanwhile, Alan struggles with his fading popularity as a "cool" parent. This episode is notable for introducing the recurring character of Miss Pasternak, who brings a mix of strict rules and spiritual intensity into the Harper household.