If something endears you to someone or if you endear yourself to them, you become popular with them and well liked by them. Their taste for gambling has endeared them to Las Vegas casino owners He has endeared himself to the American public. endear to to make someone popular and liked endear yourself to sb
If you describe someone's behaviour as endearing, you mean that it causes you to feel very fond of them. She has such an endearing personality Henry's lisp is so endearing. + endearingly en·dear·ing·ly He admits endearingly to doubts and hesitations She is endearingly free of pretensions. making someone love or like you endearing qualities/traits etc