I know what you mean... but i've found ways around it becoming too boring.. You just gotta keep it interesting. If you're sick of asking the same questions, ask new ones... in fact, if you are a little weird/off the wall... that can tend to work out better.
I've applied this to my life, and have scored more dates in the last several months just because the others thought I was too interesting not to see again.
I'd just bust out with some random quirky story about me of when I was 9 and I had a porcelain ET doll that I made a little sign for it to hold that said "I'm Matt's Friend" and used to put it in my window before I left for school, so when I came home... my friend was waiting for me. (or some other inane story, that was interesting because it was different than normal convo)
Instead of asking about their families, or where they went to school... ask them if they have any fetishes that they obsess about...
I remember when I first met my current girlfriend.... we were just chit-chatting, and out of nowhere I just said "I like pudding" ... she laughed at the randomness of that comment, and it sparked several more hours of entertaining conversation.
So if you are sick of getting the same answers to the same questions, ask new ones. The definition of insanity is doing the same thing over and over, yet expecting a different result.