Would you date yourself?

I was talking to a friend online tonight and he told me that one of the things he realized was wrong with his relationships (after the fact, sadly for him) was that he had not answered a critical question:

Would he date himself?

And ultimately, he realized he couldn't. He smokes a pack a day, is relatively uninterested in what others have to say, and (from my vantage point) is a great guy but doesn't really try to remember what others had said in conversation, generally the little things that make connection happen.

Generally, I think he is on the right path, so I'm not too worried, but I guess I wanted to ask everyone, would you date yourself? If so, why? And if not, why not?