I think a good rule of thumb is to default to assuming a question is asked in good faith (i.e. it's not a trick question). That goes for human beings and chat/AI models.

In fact, it's particularly true for AI models because the question could have been generated by some kind of automated process. e.g. I write my schedule out and then ask the model to plan my day. The "go 50 metres to car wash" bit might just be a step in my day.

Rule of thumb for who, humans or chatbots? For a human, who has their own wants and values, I think it makes perfect sense to wonder what on earth made the interlocutor ask that.