Growth mixture modeling with a sample of 749 Mexican heritage families identified parallel trajectories of adolescents’ and their mothers’ heritage cultural values and parallel trajectories of adolescents’ and their fathers’ heritage cultural values from Grades 5 to 10. Parallel trajectory profiles were then used to test cultural gap-distress theory that predicts increased parent–adolescent conflict and adolescent psychopathology over time when adolescents become less aligned with Mexican heritage values compared to their parents. Six similar parallel profiles were identified for the mother–youth and father–youth dyads, but only one of the six was consistent with the hypothesized problem gap pattern in which adolescents’ values were declining over time to become more discrepant from their parents. When compared to families in the other trajectory groups as a whole, mothers in the mother–adolescent problem gap trajectory group reported higher levels of mother–adolescent conflict in the 10th grade that accounted for subsequent increases in internalizing and externalizing symptoms assessed in 12th grade. Although the findings provided some support for cultural gap-distress predictions, they were not replicated with adolescent report of conflict nor with the father–adolescent trajectory group analyses. Exploratory pairwise comparisons between all six mother–adolescent trajectory groups revealed additional differences that qualified and extended these findings.