An act of charity can also be viewed as yet another voluntary transaction where each side expects to be bettered in some way by doing it. The recipient will have this money that they need, and the giver will feel a sense of satisfaction. In both cases we are talking about a much more psychological and emotional set of positives than would be key components in non-charitable voluntary transactions. In those, like buying a meal at a restaurant, the restaurant owner expects to make a profit and further his career, and the diner expects to get a good meal that is worth more, to him, than he is paying.
Because the voluntary non-charitable transaction is more concrete and material than the charitable act, it is easier to measure values and expectations can be resolved (or disappointed) more obviously. For example, it the menu has a photo of a large, juicy cheeseburger, and describes it as having half of a pound of beef, but comes as a tiny thing that barely has any meat, that failure of expectations, if it were done intentionally, or knowingly, would be fraud. I mention this because in a charitable transaction expectations and honesty are just as prevalent, but not as obvious. Each party to a charitable contribution should be as explicit and honest as they can be about what would otherwise go as unstated and unknown terms of an 'agreement' (I put 'agreement' in quotes because this is where the unstated can easily be the unagreed upon).
The donor should state why he is giving the gift, what it provides for him and what he expects will be done with it. And the recipient should express an honest reaction, ask if he can use it for other than paying down debt, or whatever. Because much of the value to each side in such a transaction is hidden - psychological - there will be great value in clearing the air in an honest fashion. That makes it possible for the donor to get the most satisfaction out of helping and the least chance of feeling cheated, or frustrated. It has the potential for letting the recipient feel free of guilt and opens the way for him to feel gratitude.
"Bob, we've been friends since high school and through the years you've been a great help to me. It hurts to see how tough things have been since you lost your job. I had a really good year, and I'm not saying that to make you feel bad, but to let you know that I won't miss this." Tom hands Bob a check with a fairly large amount specified. "It will make me feel really good to know that you can pay down some debts and buy a little time till things get better."
Bob looks at the check and has the sense to say nothing for a moment and to let himself feel a deep gratitude for having that kind of friend. Then he turns to the task of wondering if it would be right to take it, and what consequences it might have. He tells Tom, "I can't tell you how much it means that you would offer this. Instead of paying down debt, I want to take my wife for a short holiday. It has worn on her and she has put up with it. Would you feel that was an abuse, even in a tiny way, of this money?" Then he attempts to create something that he can offer in exchange. "Tom, if I take this, it will be on the condition that I can find something to do for you - even if it is years down the road. Maybe send you and Mary on a trip."
If Tom doesn't like the idea of the money being used for a vacation, and he doesn't say so, then that becomes his problem. Like Joe said, money is fungible, and every thing Bob purchases down the road becomes a possible source of irritation. That is just something that might come with the territory. Donors will get more satisfaction from their giving if they give up control or even judgments of that kind down the road and instead focus on what they value about the recipient and what that makes them feel.
There is a big difference between feeling entitled and feeling worthy. And a person who feels a strong sense of personal worth is far less likely to experience (or tolerate) any sense of being owned or controlled as a consequence of accepting charity. And high self-esteem is far more likely to make all charitable giving something that comes from the heart as opposed to coming from guilt or duty. People with higher self-esteem will more naturally act towards others with respect (we project our self-respect and self-acceptance). Accepting from someone who makes you feel respected is much easier than were you to feel you were being viewed as flawed, a basket case, and incapable of taking care of yourself.