Brother Mike...I went through a very similar experience with my son's mother. After we split, we attempted to work things out a couple of months later, but lived in different places. I would always help her out when she needed money for stuff at the market, cigarettes and even a 6 pack here and there.
It wasn't until "way too many times" later of trying to help her out, that I found out she was hitting other people up and, unfortunately, got involved with pain killers. Add that to her bi-polar condition and it was a recipe for destruction
She would get mad at me when I stopped lending her money...but at that point, I was not helping her, only enabling her. I offered at one point to give me a list of stuff she needed as I would go buy it for her. I even offered to order food from the grocery store and all she had to do was pick it up. She argued that I didn't need to do that and she was capable of getting the stuff herself. Wouldn't even give a bill. I had a feeling what was going on, but didn't want to believe it.
At around that time, I stopped trying to help as I realize I was only contributing to her "needs". My heart, like yours, is in the right place. Doing the right thing for the wrong results didn't make me feel good and had to stop...which was hard to do, but was the right choice. You can only lead a horse to water.
Good luck and hope your situation is not the same as mine, but you can offer solutions like I did...I would stay far away from giving money. You're a good man and, like someone else said, makes you an easy target - Trust me, been there, done that too many times
MISFIT STRONG. MISFITS UNITED. MISFITS GOT EACH OTHERS' BACKS