An entitled friend can be a very dangerous thing. One who feels whatever another labours for, they must have a share in it because they are in a relationship with you.
It is good to help others up but the danger of those with a sense of entitlement is they will never be satisfied. Once you start feeding that sense of entitlement you are operating under the influence of a guilt-ridden conscience and by that, you are now being manipulated.
The longer you feed their sense of entitlement the more you justify their claims and you get weaker. It starts with emotional blackmail but the entitled one will seek to find more tangible things they can use to blackmail you so as to keep their host in bondage as they live off him or her as parasites.
Cut it off early.