It's hard to say no to those we love and genuinely want to help. But if life has taught me anything, it is that sometimes saying no is the best way to help someone. Otherwise, you become the solution to every problem they have and they never learn the skills to be self-reliant. I hope you will continue to have the strength to help your sister in the way that is not always the easiest, but the most beneficial in the long run. Best of luck to you and your sister.
Update, of sorts...
Thanks for the thoughts. Taking her out to dinner is difficult...she lives in Phoenix, AZ, I live in Kansas City.
I DID, however, get to send her a text a few days ago. One particular Christmas classic was on television that always makes me think of her, so I sent a text saying as much. We chatted back and forth for a while, and while she never specifically asked me for any money, she did start sharing her financial woes and complaints and I eventually was able to change the subject, but it was uncomfortable.
Hmph. Progress, I suppose, but no solution yet.
Not to make light of your situation because I know it must be breaking your heart, but I heard a guy comment once, "I don't know why my brother's been mad at me so long, I never loaned him any money."
I've had a similar situation with my brother a few times. He's 51 years old. I just turned 60. All his life, he has struggled financially. It seems that he's always in one sort of money crisis or another.
I've loaned him a lot over the years, and he has always paid me back. Eventually. But every single time he needs a loan, he says "I will pay you back next week" or "I will pay you back at the end of the month". Well, he was rarely able to pay me back when he said he would, and when that happened, he would disappear from my life until he was able to pay me back.
So about a year ago, he needed to borrow money. He had no outstanding loans from me, so I had no problem with loaning him what he needed. When he said, "I will pay you back in two weeks", I said, "Let's just leave it at 'You'll pay me back as soon as you're able'". He asked me why, and I told him that he's always overly optimistic about when he'll be able to repay, and then he gets bummed out and embarassed and avoids me until he IS able to pay. I let him know that the ONLY hesitation I ever have about loaning him money is that it might trigger his absence from my life, and I don't like that.
He seemed very relieved to hear this, and the loan was given and repaid without a hitch. Not in two weeks, as he wanted to promise, but in a month.
Just last week, he needed a loan of $450. He said, "I can pay you back in two weeks". I said, "Nope. Can't do it." He had seemingly forgotten our previous discussion. He thought a minute, then said, "I need to borrow $450, if you can loan it to me. I will pay you back as soon as possible." We sealed the deal.
That IS awesome. Yay both of you!
Yesterday was her birthday. Got to chitty chat a bit and wish her a happy one. (She's 52, so I also asked her if she is now playing with a full deck, she assured me that she isn't and doesn't intend to.)
Dollars were not specifically mentioned. She did lose her rental home and is currently sleeping on her adult daughters couch. (Bet that is all kinds of awesome! Not)
So no real progress on the financial front, but we did get to chat for a bit at least.