Here's two of my favorite's. Fortunately for them both these were over the phone so I couldn't reach over the table and smack them. I will abridge them in the interest of interestingness.
Scene 1:
Her: Can you tell me my ex-boyfriend and I will get back together.
Me: This one's most likely over.
Her: I haven't heard from him in awhile. Do think we can still be friends?
Me: How long is "awhile"?
Her: Eight years.
Me: Then I think you already know the answer, right?
Her: Yeah...Can you tell me about my relationship with my husband?
Moral: If you can't be with the one you love, love the one you're with. Then again, maybe some people should learn how to be alone.
Scene 2:
Him: My girlfriend can't have kids.
Me: ...(waiting for the question)...Okay?
Him: I want to have kids but she can't.
Me: I'm sorry, what exactly are you asking me?
Him: She can't have kids so I'm going to have one with someone else. (As you can see, this is a declaration of intent and not a question.)
This guy wanted me to tell him to go ahead and cheat on his girlfriend. God, I hope she has some good friends that helped her to see what a jerk he is.
Peace,
April