Although there have been recent advances in knowledge and thinking regarding life history conceptualizations of psychopathology, there is still a missing link. That is, although life history strategies may set the stage for the development of various psychopathologies, we believe there is a missing key factor in understanding individuals’ risk profiles of psychopathology. This study explored whether schemas and expectations might help differentiate between those who experience psychopathology and those who do not in a student and community sample. In the current cross-sectional study (N = 378), we examined the associations between life history indicators and experiences of anxiety, depression, obsessive–compulsive symptomatology, and substance use, as well as the possible mediating and moderating effects of schema and expectations on the associations, respectively. We found several significant mediational pathways with indicators of a faster life strategy predicting increased levels of dysfunctional schemas, and in turn predicting increased experiences of depression, anxiety, and obsessive–compulsive symptomatology, but not substance use. Moreover, although expectations did not significantly moderate the mediational pathways, expectations were a significant predictor of depression and anxiety, with those who reported having their expectations rarely met reporting increased experiences of depression and anxiety. Although this research is preliminary in nature, it has provided initial insight into how our schemas and expectations might play a role, alongside life history strategies, in better understanding individuals’ risk profiles for psychopathology.