One aspect of emotional development in adolescence is the motivation to express negative emotions to others that is linked to a wide range of psychosocial outcomes (Chaplin et al. Emotion 5:80–88, 2005). Supportive and unsupportive parental emotion socialization responses to adolescent emotional displays are one mechanism that influences adolescent emotional functioning (Garside and Klimes-Dougan Sex Roles 47:115–128, 2002). The present study explored five parental socialization responses to anger, sadness, and worry and how they may differ for youth who vary in their reluctance to express emotions. Participants were 160 adolescents and their parent (74.4% mothers; 58.8% girls, Mage = 12.5 years, 78.1% White, middle-class). Parents reported on their responses to their child’s emotion expressivity and youth reported on their reluctance to express emotions. Using latent class analyses, two groups of adolescents were identified, including those with high (n = 36) and typical (n = 124) levels of reluctance to express emotion. Group and gender effects were examined. Parents reported more validation and less ignoring of negative emotions for adolescents in the typical rather than the high reluctance group. Parents reported more magnification of emotions in response to adolescents’ anger in the typical group in comparison to the high reluctance group, and more magnification of sadness for daughters than for sons. These results suggest that differing levels of adolescents’ reluctance to express emotions are related to parental emotion socialization responses in meaningful ways that may play unique roles in promoting or discouraging the expression of negative emotions.