This study compared 51 adolescents from intact two-mother planned lesbian families (all conceived through donor insemination) with 51 adolescents from intact mother– father families on their relationships with their parents (parental control, disclosure to parents, and adolescent– parent relationship quality), psychological adjustment (selfesteem, social anxiety, and conduct problems), and substance usage (consumption of tobacco, alcohol, and marijuana/hashish). The adolescents (average age 16 years) were matched on demographic characteristics (age, gender, educational level, country of birth, parental birth country) with a sample from a large school-based survey, and data were collected by means of adolescent self-reports. Analyses indicated that adolescents in both family types had positive relationships with their parents, which were favorably associated with psychological well-being. On the assessments of psychological adjustment and substance use, family type was significantly associated only with self-esteem and conduct problems: Adolescents with lesbian mothers had higher levels of self-esteem and lower levels of conduct problems than their counterparts in heterosexual-parent families. Overall, the findings indicate that adolescents from intact two-mother lesbian families are comparable to those in a matched comparison group with intact mother–father families. The few differences found on psychological wellbeing favored the adolescents in lesbian two-mother families.