theonlyblaze2 said:
Friend: "Dude, is your sister hot?"
Me: "Um...she is my sister,...and twelve."
Friend: "...So is she hot?"
That's happened to me. Only my sister was TEN at the time.
The most awkward conversation I've had would probably be when my dad found... explicit furry images in Internet Explorer's browsing history. I would never touch that crap (I mean, seriously. Internet Explorer!? Disgusting!), but I had recently had a friend over... And I knew he was into that sort of thing. Dad, of course, blamed it on me, and I had to spend half an hour explaining to him that it was the friend that my parents have grown to love like another son after about 14 years. It was pretty weird, to say the least...
The runner up would probably be when my cousin saw my Facebook profile, and how it had 'Men' checked in the 'Interested In...' selection, and promptly called the rest of the family to tell EVERYONE. Let me tell you, of all the ways to come out of the closet to your parents, that would have to be the WORST. Telling the internet before telling my family was my most regretted action ever.