Tl:Dr - a friend/acquaintance of mine pops up every so often asking to borrow money, always under the pretence of "ran out of food and don't get paid for a few days." I'm starting to feel a little bit resentful as I feel like they are using me and I am starting to suspect they are lying to me about some things that are going on. The money never gets paid back but I have accepted that when they ask to borrow I am actually gifting them the money. Is it ok to say no even when they are saying they are in desperate need?
Long version - I've known her for a while, since she was a teenager. Just after I first met her she said her mom had kicked her out several times then asked her to leave for good due to her coming out as LGBT. I was furious and heartbroken on her behalf and didn't hesitate to help her in any way that I could, such as driving her to her girlfriends house where she now lives (which is a long distance away) when public transport was cancelled or giving her money to help with practical needs.
However, while I know things are not always as they seem online, I have recently seen some social media posts which strongly suggest that she actually has a good relationship with her mom and that when she moved out to go live with her girlfriend it was actually her choice and was done with her mom's blessing. While I don't know the ins and outs, I'm now wondering if things didn't happen the way she presented it to me at the time.
I've given her lots of money in the past, usually in small amounts of $10-$30 and I didn't mind at the time but it's all starting to add up and I'm starting to feel resentful at the thought that she is just using me as a cash machine. What I generally find is that I won't hear from her for ages then when she gets in contact in desperate need of help I'll give her a small amount then she'll keep messaging asking for more until it starts to add up and I say no then I don't hear from her for a while again and so on. Also in the past I have suggested I could help her look for other sources of income such as state benefits or funding from LGBT charities that she may be entitled to but she has always declined this and my offers to help her ways other than financially. Again, from what I see on social media I'm starting to get the feeling that she is trying to live beyond her means and that by giving her money I may just be funding an irresponsible lifestyle.
So is it ok to say no to giving money even when she is presenting it as a desperate need such as "I haven't eaten in several days and don't get paid until next week"? I would feel awful and heartless for saying no in those circumstances but I'm not sure how true it is. We're not that close anymore and I think there must be a long line of people that she would be able to ask before me that would be willing to help her if she was in genuine need, I think she jumps straight to me cause she knows more often than not I'll say yes. Today when she messaged asking I suggested she ask her relatives for help but she just said "no unfortunately I can't" Can I put my foot down here without looking and feeling completely heartless? Should I talk to her about what I saw on social media and ask her about what's really going on?
