Similar cognitive processes enable us to remember the past (i.e., episodic memory) and simulate future events (i.e., episodic simulation). In the current study, we demonstrate an important role for previous experience when younger and older adults simulate future behaviours. Participants read short descriptions of a person in need of help in scenarios that were more familiar to either younger or older adults (e.g., dealing with dating apps vs writing a cheque). Participants either imagined helping the person or thought about the style of the story (control task), and then rated their willingness to help, scene vividness, emotional concern, and subjective use of theory of mind. Hierarchical mixed effect modelling revealed that both episodic simulation and one’s previous experience increased willingness to help, in that participants were more willing to help if they imagined helping and the situation was more familiar to them. Further, in simulated scenarios the relationship between previous experience and willingness to help was mediated by scene vividness and perspective-taking in younger adults, but only by perspective-taking in older adults. Taken together, these findings suggest that situation similarity and episodic simulation increase willingness to help, possibly via different mechanisms in younger and older adults.