Recently, it has been demonstrated that wisdom positively predicted well-being. The paradox is that the development of wisdom is strongly linked to adverse experiences that can make a person feel “wiser but sadder”. This paper aims to test whether two types of dialogues with oneself, i.e. integrative and identity internal dialogues moderate the relationships of critical life experiences and reminiscence/reflectiveness (as components of wisdom) with psychological well-being. To check this, 202 women and 217 men completed four measures: Self-Assessed Wisdom Scale, Psychological Well-Being Scales, Internal Dialogical Activity Scale—Revised, and Scale of Integration of Perspectives. It was found that critical life experiences and reminiscence/reflectiveness poorly (usually negatively) or not at all predict the general well-being and its dimensions. Integrative and identity internal dialogues moderate these relationships: with a higher intensity of these dialogues the negative relationships weaken, insignificant ones become positively significant, and positive links strengthen. The findings can be used by psychologists to promote the development of clients’ wisdom, and consequently, well-being.