Teachers (and parents), responsible for the acculturation of young children, have an investment in "niceness". While the moral worthiness of this norm is obvious, niceness when enshrined as a set of rules is questionable. Because we want children to be honest, strong-minded and bold, to resist peer pressure and speak out against wrongdoing, protection against hurt must sometimes give way to other priorities. Through the presentation of two early childhood scenarios - a small child asks questions of strangers that insult them; a somewhat older one rejects the overture of a child who wants to join his play - I explore the downside of tactfulness and the difficulties of determining who is injured by bluntness. The argument proceeds that in order to balance both the interests of the parties and the different values at stake - fairness as well as niceness - we need to contextualise our judgements by avoiding general rules. Finally, I suggest several benchmarks that should be incorporated into this contextualised decision-making - the act itself, its consequences and the motives and personal history of the players.