This study investigated contact and ageism on both the implicit and the explicit level. We examined the role of grandparent–grandchild communication (in terms of self-disclosure) and its relations to anxiety and empathy in improving intergenerational attitudes. Analyses revealed that: (1) quantity and quality of contact with older people (other than grandparents) predict higher levels of self-disclosure (to one's grandparent); (2) quantity (but not quality) of contact with older people is associated with more favorable implicit associations with them, while quality of contact is associated with more favorable explicit attitudes; and (3) higher levels of self-disclosure to grandparents are associated with empathy and reduced anxiety, which in turn are associated with more positive explicit attitudes toward older adults. We explain our findings in light of the environmental associations model (Karpinsky & Hilton, 2001)—that quantity of contact, or mere exposure to older people, drives the Implicit Association Test effect. The model sheds light on the mediational roles of interpersonal variables (self-disclosure, anxiety, and empathy with a grandparent) in intergenerational contact.