He has a considerable sum of money. Have you read Steve's article about where he says people have different views on money? For example, an ultra-wealthy person thinks nothing of spending a few thousand dollars in a hotel for one night, while that would be viewed as extremely "wasteful" for someone coming from a more scarce mindset.
Consider the position of abundance he comes from. He might think of buying you groceries as just getting rid of some pocket change. Then to him, it's really no skin off his back if he bought you some groceries or helped you with your rent. It'd be similar to a regular guy buying you dinner.
In that case, his gifts to you are just a small gift from his emotional perspective. You might think of it as "using" him because you come from a scarcer mindset, but it isn't that way to him at all. To him its like a regular guy giving you the quarters in his pocket.
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