The first purpose of this study was to investigate the direct effects of three subtypes of social withdrawal (shyness, social avoidance, and unsociability, respectively) on internalizing outcomes (depression, emotional dysregulation, and self-worth, respectively) in emerging adulthood and to examine these effects by gender. A second purpose was to examine if parenting moderates (i.e., exacerbates or buffers) the main effects of social withdrawal on internalizing outcomes. Participants included 790 undergraduate students from four universities in the United States (Mage = 19.61, SD = 1.85, range = 18–29; 243 males, 547 females) and their mothers. Regression analyses established that shyness was associated with higher levels of depression and emotional dysregulation as well as lower self-worth for males and females. Social avoidance was linked with higher levels of depression and emotional dysregulation for females only. Finally, unsociability was associated with lower levels of depression and dysregulation for both genders. Analyses also established that parenting did not moderate depression, emotional dysregulation, or self-worth with regard to shyness or social avoidance. However, helicopter parenting moderated the links between unsociability and depression. Authoritative parenting moderated the links between unsociability and dysregulation and self-worth. Discussion focuses on the outcomes for emerging adults and the moderating roles of gender and parenting.