Intergenerational narratives, stories parents share with children about their own youthful experiences, may facilitate the understanding of challenging life experiences and be related to psychological well-being; yet, little research has examined what young people know of their parents' self-challenging and self-enhancing experiences and how they interpret them. Research examining intergenerational narratives has observed relations between adolescents' narratives and their psychological well-being, but these relations may depend upon gender and narrative type. In the current study, 94 college students provided intergenerational and personal narratives of transgression and pride experiences. Narratives were coded for emotional, cognitive, and evaluative content. Results show that transgression and pride narratives differed in content, and that women provided more interpretative content than men. Stories about mothers contained more interpretative content than fathers, but this pattern varied by participant gender. Finally, relations to well-being were observed, especially for cognitive content in stories of participants' same-gender parent.