In everyday life, individuals often need to make choices about the difficulty level of tasks they wish to perform. Here, we investigate age- and gender-related differences in the monitoring of discrepancies between the difficulty of a given task and one's own performance level, and in the likelihood to select task difficulties that match one's performance level. Male and female children, teenagers, younger adults, and older adults (total N = 160) were asked to play a modified version of the BINGO game. Task difficulty was operationalized as the number of cards played simultaneously. We expected that (a) discrepancies between individuals' self-selected difficulty levels and their objectively assessed maximum manageable task difficulty (MMTD) would be lowest in early adulthood; (b) children and teenagers, on average, would select relatively difficult task difficulties; and (c) males would overestimate their performance levels, on average, to a greater extent than females. As predicted, younger adults selected task difficulties closest to their MMTD. All other age groups, including older adults, chose task difficulties above their MMTD. The expected gender differences were restricted to children, with boys showing more pronounced performance overestimations than girls. Children and teenagers fluctuated more in their difficulty choices than adults, and many of them, especially boys, occasionally chose difficulty levels far beyond their performance capabilities. We conclude that task-difficulty choices are an interesting topic for lifespan studies. Future research should systematically vary the physical risk involved in a task, and also include the presence of peers.