In the current study, I examined the effects of age, explicitness of instructional materials, and personality differences on risky decision making while playing the Game of Dice Task (GDT). Participants were randomly assigned to one of two instruction conditions: Explicit vs. Standard. In the explicit condition, the instructions were very straightforward, with respect to risk, while the instructions in the standard condition were not. To describe this game in more detail, in the GDT, participants decide how risky they wish to be on each trial. To optimize performance, participants should make “safe” rather than risky choices. Overall, older adults were riskier than younger adults on the GDT even though they self-report being more risk averse than younger adults in several different risk domains except for social. In regards to the instruction condition, there were no significant age differences in the standard condition. Younger and older adults perform similarly. However, there were age differences in the explicit condition. Older adults were riskier in the explicit condition than younger adults were. In addition, a 3-way interaction between age, instruction, and conscientiousness was discovered. Older adults who are low in conscientiousness perform similar to regular older adults in the standard and explicit conditions. However, the effect of instruction condition disappears for those who are high in conscientiousness.