I have a problem somewhat similar to the roommate rant that spawned Grimsqueaker's epic advice. If you're around, GS, could you chime in?
I have a friend who is a nice person and has genuinely been shit on by life. Crappy upbringing, health problems, chronic underemployment. We see her every six months when she's in town. The problem is, like the title of this thread, every time I spend time with her she asks for something more and it's really starting to get to me.
We went out for dinner last night. My husband and I both work full-time. She's staying with a friend and planning a trip up the coast on Thursday. She started making plans for staying with us on Wednesday night, because we're closer to the train station. And she'd need us to pick her up from what she was doing that night because she doesn't have a car. My husband said, 'Have you asked spiffsome about this?' Eventually we worked out that he and I both had commitments that night and someone would need to pick her up about 10 pm, bring her home and then go to work the next day. I said it was too complicated and she decided to ask someone else. Absolutely no indication that she was aware that this was a significant favour to ask. All of her plans are last minute because she's one of those people who doesn't 'do' plans.
I have made progress - previously I would go along with the plans because she's nice and having some one to stay really isn't a big thing, then rage to my husband afterwards about how some people don't know when to go home. This time, he said 'You're going to have to check that with spiffsome' and I said no. Success, right? Unfortunately, I'm getting to the point where I just don't want to see this woman because I'm sick of fielding these requests.
I would, if possible, like to preserve the relationship. She's a nice person apart from the 'doesn't hurt to ask' habit. She seems genuinely anxious to have my approval. Also, I'm happy with the way my husband is now handling it - I'm comfortable with owning my own decisions.