In the spirit of II season starting up, I was thinking of this notoriously difficult question to answer during an interview. Some people will have something that is easy for them to point to, but I was wondering what some inappropriate answers would be? Is breaking up with a SO of several years a good example of a difficult decision or would an interviewer see that as trivial? The last thing I want to do is to come off as the person who seems like "Oh my life has been great and I haven't had any significant difficulties."