The effectiveness of two online exercises intended to help individuals experience (1) self-compassion (n = 63) and (2) optimism (n = 55) were compared to a control intervention where participants wrote about an early memory (n = 70). A battery of tests was completed at 1 week following the exercise period, and at 1-, 3-, and 6-month follow-ups. Both active interventions resulted in significant increases in happiness observable at 6 months and significant decreases in depression sustained up to 3 months. The interventions were examined in relationship to dependency and self-criticism, both related to vulnerability to depression. Individuals high in self-criticism became happier at 1 week and at 1 month in the optimism condition in the repeated measures analysis. A sensitivity test using multi-level modeling failed to replicate this effect. More mature levels of dependence (connectedness) were related to improvements in mood up to 6 months in the self-compassion condition. This study suggests that different personality orientations may show greater gains from particular types of positive psychology interventions.