This study examined how adolescents recall and interpret caregivers’ personal stories about a difficult time. Respondents were 49 ethnically diverse adolescents (M = 15.76 years; 63% girls; 53% from immigrant families). Analyses examined story features (topic, narrator, elaboration, and meaning) and variations due to gender, age, and immigrant background. Four overarching topic categories were identified: family hardship (39.5%), caregiver’s personal problems (25.6%), family interactions and dynamics (20.9%), and interpersonal situations outside family (14%). Youth extracted a variety of personal lessons from caregiver stories, with meanings differing across some topic categories (e.g., stories about family hardship typically emphasized that youth should persevere/work hard). Story features differed based on characteristics of storyteller and listener, particularly gender and immigrant background. For example, adolescents (particularly girls) were most likely to narrate a story heard from their mother, and more boys than girls retold stories emphasizing perseverance and hard work. Adolescents from immigrant families told stories that were more elaborated than those told by nonimmigrant youth, and stories told by caregivers reflected unique life experiences and goals. Findings contribute to the literature on family storytelling and have implications for future research and practice with diverse populations.