I understand. I have people in my life like that, and I am inclined to want to help others. At one time I could afford to help, now my finances are drastically different, so it makes it easy to say no.
What I have come to realize is that even when I say no, they manage to survive. She will figure it out. She is taking advantage of your kind and generous nature, and she is not your responsibility.
In my case, my generosity was about me, in the end. I had a need to replay my role in my family, miss fix it, she who will come through, she from whom all blessings flow. I have set people up to depend on me, and then resent the hell out of them when they do, I am not suggesting you are twisted like moi at all by the way. I have found that I am now able to help when I feel like it, not when it's expected or demanded, and I don't end up feeling used and abused. And a more difficult lesson for me has been to accept help and let others feel good about being generous and helpful.

You are many things, brave, courageous, grace under fire, but you are not a bank. Take care of YOU.

You have to know your limitations, and you have to do what you can to protect yourself, and that includes financially. I hate to say this, but your description of her would make me suspicious of the reason she needed the money, especially saying she needed it right away (sounds like drugs to me, but that's just my suspicious nature).

I had a situation arise with my son's friend. My boys are disabled, and this young man is too. His mother is dead, and his father was arrested and their home condemned by the drug squad. He came home to find he could not get into their home, his father in jail, and nowhere to go. I took him in, fed him, clothed him, and did what I could to find resources for him, and bought him a cheap phone to use in case of emergencies. He asked to live with me and my sons permanently. I had to turn him down. I had my hands full already as a single mom of two disabled guys. I did take care of him until his father was out on bail and had found another place to live. It broke my heart to do it, but at some point you have to let others step up to the plate to help.

If you believe she has legitimate reasons for her hardships, you could make some phone calls to find her help elsewhere. There are organizations and programs out there that can help. Have you ever heard the old saying, "Give a man a fish and you feed him for a day. Teach a man to fish and you feed him for a lifetime,"? Giving her more money may not be the way to help her in the long run. Just my thoughts on that....

You have nothing to feel guilty about. You've been a good friend, probably too good.

Love and Hugs,
Martha

I fully understand the guilt feeling, but you did give her money and you know you will probably not see it again, so really she should be thankful for that. When it comes to people expecting to receive all the time then this is not a healthy situation, and it is a concern that can bring many many problems, problems you don't really need. I am sure if she is motivated enough she will seek the help. Sound to me she is more than capable of getting out there and doing things that need to be done to support her family. We all struggle in many areas of life, financially being a big one for a lot of people, but there is help out there, and we learn to adjust to situations, cut back on things, downsize our living space to survive and so on.

The guilt feeling is understandable, but you can only do so much, and you went above and beyond like a good person would, but sadly some will try to take advantage of that, or see that kindness as their escape out of a problem.

I think its natural to feel guilty as you would like to help her but this time you cant. You have helped her in the past and should feel good about that. You need to take care of yourself first and help where you can.
Russ

rainycreek said it well - even when I say no, they manage to survive.

My sister in law is like that. She is the baby in my wife's family ( 46 now ) and she always sat for our kids when they were young. She is a single mother and always has money issues ( always has a payday loan, if you know what that is ). We always would hire her to clean our house when she was short of money, and other times we would loan her $100 ( that we knew we would not get back ).

Couple of weeks ago she asked for $650. I could have given it to her, but she would have in the same fix next month. I told her I could not give her the 650 because she needed to adjust her spending or she would be in the same fix. My wife had a $100 bill in her purse so I offered that to her. She came by and got that, but has not talked to me since.

Unless you are going to adopt or marry somebody you can't take care of them - its their job to do that.

Also, for some reason they don't like you even when you help them, lol.

Sometimes you just have to say no. It sounds like you helped her more than once already and hopefully she is thankful for that--but this time obviously your gut told you it was time to say no--listen to your gut. I have to agree with others that sometimes helping isn't helping--they just keep getting back in the same situation. Try not to feel guilty--you aren't being unkind or selfish--you are being responsible. Sometimes it's just time to let people know we are not the "1st Bank of their convenience". Hugs, Wanda

You feel bad because you have a kind heart, but there is no reason to feel bad. Our feelings often take on a life of their own. Because there are people worse off than others we want to help. I understand your feelings. You have gone the extra mile for her and you need to know that. Now you need to do what is right for you and your future. Send your prayers her way and know that is a gift you can share with others. There are always circumstances to overcome in the world. It is sad, but true, but you have been very generous and you have helped her. Sharon

Thank you for everyone's response. My co-worker is a good person, not on drug. She just took on too much responsibilities caring for everyone. They have low paying jobs and can't get ahead. She would have to win a lottery to get out of her predicament. I have given her a lot of money already and it is just hard for me to give more when I too have a lot of bills to take care of. My children all thought I was very generous towards her when I told them the amount I have given out.

I read this right after my oldest daughter and I just got into a huge argument and she left. She wants me to put her up in an apt and pay for all the bills....to help her get out of her living arrangement which is living with her daughters great grandmother. Really? I am my only income. And then got mad cuz I wouldn't let her live with me here...she is nothing but drama! Jim would be mad at me for helping her after he moved on. I paid off her $3000.00 court fines to keep her out of jail and got her a phone she doesn't have to pay for. It hurts not to help her, but what else can I do? Now I'm venting...lol