Most of my siblings and close friends have less money than me. In some cases, they did not save for retirement or mismanaged their money but mostly they were divorcees or singles with children in lower paying professions. Where this tends to be a problem is when we vacation together. I would prefer staying in nicer hotels (e.g., with an ocean view or an historic hotel within a national park) and eating at nicer restaurants and visiting better attractions. Usually we are sharing a hotel room as having separate rooms would be a big budget buster for them. While I am willing to pay extra, they want to split the costs evenly and this makes it awkward.
We solve this issue by renting our own VRBO property and then inviting others to join us at no cost to them. Since their lodging is free, and we are spending about what we would anyway, we all have money left over for activities and nice dinners out. The properties have kitchens so we can eat breakfast and occasionally dinner together at home.