I’ve had a bit of a journey with generosity. Hopefully, give the outline of the process, avoid the full saga.
I lived in a certain locality in the countryside from age 26. My wife was the same age, and we had a baby girl. A number of us had wound up there, as it was beautiful and cheap to get shelter (old cabins, sheds, converted chicken coops, etc). My friends & acquaintances were amicable, sensitive to nature, eager for experiences. Most of us got employment wherever we could. Few had much money very often, but the “bubble” I was in had it seeming that a new age of mutuality was upon us.
From the start, I was probably more generous than was realistically prudent. Loaning tools, letting people stay in our cabin (sleeping bag, foamy on the floor), sharing meals. Over time true colors showed, maybe only half the people were firmly reciprocal. With those people there weren't doubts about assistance when needed.
At 28, my (first) wife decided that she wanted to experience life more as her 18-year-old self had, which ended the relationship. I went through a difficult patch during that time, and sometimes asked friends for favors… which weren't always forthcoming. About 18 months after the split with my wife, I met a new woman with more practicality & mature values. We lived together and after a couple years, she deemed my habits to be a bit too generous. And she pointed out ways in which certain people I’d considered friends were opportunistic, not very reciprocal.
By the time we were in our mid 30s, my new partner finally had enough. Thus started a new phase of my life... we moved to another location in the valley. I felt rather abraded by my previous experience. (A voice in my head wanted to request a résumé from anyone who seemed to desire being a friend. LOL) But I learned to get to know people better before taking risks (with tools, time, or $$) — and to firmly communicate my expectations in any matter of $$.
I became a much better judge of character. In my current phase of life, I’ve long felt freer again. I enjoy being generous within my capabilities.