Is the word "regret" ever used in a positive context? The word is defined in most senses as "sorrow" over a circumstance or one's own, presumably, grave failure or error. When we regret something, unless we use the word in the social sense, it's usually something major, with consequences: "I regret not mentoring my top people better because I think that's what cost me the promotion" (more on this example later). By contrast, people generally don't regret forgetting to return a borrowed pen. Other common uses of the word imply extreme, often permanent, damage done, as in the threat "You'll regret this!" When someone claims to have "no regrets," there's a kind of satisfaction or pride implicit in the statement, as if regret were a sign that one has really blown it. Regret, it seems, is the one feeling you don't want to leave any situation with.