This article offers an analysis of various situations of moral dilemma generated by the Bodhisattva idial of extreme self-sacrifice, with special reference to the career of Vessantara. The analysis focuses on the dilemmas resulting from his marvelous giving of gifts (dana), as a prince of a kingdom, as a royal son to his parents, as a husband and as a father. Emhasis will be directed to the various lines of reasoning, both supportive and oppositional to the gift giving, voiced by the people around him who were directly effected by his generously. Finally, some possibilities for reconciliation will be explored.