Straight-forward, neutral approach
I feel that this question needs an answer that takes it at face value, skipping any guessing about what kind of dating the OP is doing, and whether anyone has a hidden agenda.
My stance on money is this: I do not lend, but I give gifts. It does not matter if it's family or not, or if it's important or not, if it's my children, wife, parents or any stranger.
This means: when I give money to somebody I not only never expect it back, but I always make completely sure that it is a gift.
A very important part is that if I give a gift, then I do it happily and freely, i.e. no "I don't want to give you money, but here you are anyway, keep it". No grumpy giving.
This works surprisingly well. People know exactly what's up. People who like me and have good intentions don't ask for money because they know that I would only ever gift it, not lend it. Or, if they are really in an essential crisis, they may ask me, but will not ask for lending, but for giving.
If someone would ask me and I were not willing to give, I still have all options open to me. I can just say "no" as usual. Or I can, strategically, say "fine, but I do not lend money: this is yours, it is a gift, I don't want it back". I might do that once or twice (and I probably won't, then, take it back, even if they try, at least not without making a scene of it ;) ). People who know that they will get a gift instead of lending will think twice before asking for more and more, because there is no pretense of giving it back somewhere in the far future. Obviously, at any point of time I can switch to saying "no".
Also, this makes it very easy for me to decide whether to say "yes" or "no". If I can afford to let go of that money, if it does not hurt me, if the priorities (between losing the money, and the feeling of helping the receiver) allow it, then I give. If the balance does not work out, then I do not. Guessing whether I will get it back never enters the decision.
Oh, and obviously I do not lend money from others, either.
(There is a small exception to this: sometimes, for example when going to lunch with colleagues, people cannot pay because they only have a credit card and the place we're at does not take the card - for things like this, obviously, I will not only cover their meal, but will then also take the money when they give it back to me later; I do not consider this "lending" in the strict sense, just fixing a short time difference so the other guy has a chance to visit a bank and draw some cash. But even in this case, if they happen to forget about it, I won't bother them, I won't keep a "balance"; I might remind them when we go out to eat next time, so they will pay my meal then.)