Personality quirk that I like least about myself:
I HATE talking about personal situations with co-workers, especially bosses. So much so that I end up sounding weird and feel like I sound like I'm lying. I hope I really don't sound like I'm lying, but I suspect I do. I tend to just blurt out whatever is going on, offer little to no detail, practically cut off the other person if they try to say something comforting or nice (not intentionally), and lead with the fact that I need time off or whatever other work-related piece of the information that I can scrounge up. The ONLY time I have ever felt genuine when I was telling a supervisor about something bad happening to me was the day I found out my grandmother had passed away. I sent my supervisor an email letting her know what had happened, she called right away, and as soon as I picked up the phone, I started sobbing. Not graceful or dignified, but genuine. Oh, and when I broke my ankle, I called my supervisor and said, "I have a funny story to tell you that's not really funny at all." But that supervisor was a close friend (still is, actually). So that one doesn't really count.
So tell me - how do you tell bad news about yourself or your life to your boss? Is there a graceful way to do it?