Although the norms of advice apply across the board, their demands are context sensitive. This chapter examines the ethics of advising outside of professional exchanges. Drawing on the concept of role obligations, the ethical contours of advising strangers are traced. It is concluded that there are ways in which strangers can be better placed to advise than friends and family, if the role of ‘facework’ in upholding an advisee’s standing is attended to. However, we generally regard close friends and family as the proper people to deliver challenging advice. A case provides a basis for assessing when unwelcome advice should be given despite predicted resentment and likely futility. The chapter culminates in a summary of principles about when advice should be given or withheld in personal contexts.