Reminds me of a girl I used to know. Always wanted pity. Self-pity, pity from others - it was like food to her.
It was a strange relationship. Like she would whine to me things like, "I haven't eaten in two days."
I didn't think it was helping her to give her pity so I would say in the most direct possible terms, "I don't have pity over things you do to yourself on purpose. Do you understand? I don't have pity for you right now."
But you could tell she thought I was lying and was really feeling pity. That made her happy.
In case you're thinking maybe she was anorexic and I should have been more sensitive, no. She actually had eaten in the last two days. It was all just an idiotic game. The not eating thing is just an example. She had all kinds of things she would say that she imagined were pitiable.
I would occasionally suggest that her life could become better by just making a little effort but the truth is, I don't know what a conventional life could offer that would have given her more enjoyment than she got from being a sadsack thinking she was getting pity from everyone.