How do rich people who came from poor backgrounds handle the relationships with their still-poor friends? Do they get approached for money a lot? How do they handle these requests?

I once had a friend who, coming from a totally normal background, made a career as a very successful finance lawyer and eventually his picture ended up on a specialized magazine with a list of his highly prized clients.

Nowhere in the article it was stated specifically that he had become rich but that could be inferred even from a baby and as soon as the news spread in the business world, my friend told me the following happened:

  1. His inner-circle of close female friends started expecting him to pay dinner for them whenever they went out. This attitude changed immediately and automatically (once the bill arrived at the end of the dinner, they did not take their wallet and simply waited for him to pay, smiling) even if there was nothing more than just a good friendship between them (i.e. they were not dating): he paid them for dinner regularly as otherwise he would not be able to go out for dinner with them anymore;
  2. A former colleague who he had not seen for at least 15 years called him out of the blue to congratulate and ask him out: after a pleasant dinner, he explained that his wife and two young daughters were living an impossibly lavish life and his revenues were drying up and did not know how to deal with the expenses amassed by the wife: he had already asked money to everybody he knew (including relatives) and eventually he ended up asking him 2.500 Euros to pay certain debts with close deadlines: he gave him the money and never heard from him again;
  3. Relatives started asking for money again and again: a medical bill, unforeseen taxes, the son’s first communion, etc. There was always a new reason for them to ask money. For his extended family, he became the one to call every time there was a need for some money. Small or large sums, it made no difference: by asking for “loans” that everybody knew were not going to be repaid, the relatives were very able to tap on an emotional chord and he regularly gave them more or less any sum they asked for. Once, his own father — with whom he had extremely rare contacts — asked him for 20k Euro to pay for certain (uninsured) damages to his house;
  4. He once decided to go on a holiday to Japan with a male friend and his friend asked him to book (and pay in advance) the very expensive plane tickets for the two of them: eventually they could not make it to Japan for some reason but they could not get a reimbursement from the airline (as the ticket fare did not allow that) and the friend never repaid him any money (basically subtly “forgetting” to repay him). He told me that the friend was smart enough not to forget about asking for the Air Miles for his own (unused) ticket and getting a refund for the part of his expenses that he pre-paid in advance of the trip.
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