What do rich people who have lost everything miss most about having money?

My 68 years old uncle lost his job as a top manager in a British company in his 40s and was unable to find any job since.

When he was fired, he had accumulated quite a fortune that he estimated would have lasted him for all his remaining life (he never had kids or a spouse).

Due to medical emergencies, depression, bad friendships and decisions, he depleted his fortune in less than 20 years and he is now completely money less and lives an extremely frugal life as a retiree.

He is still resilient and upbeat, and I speak frequently with him about his life, what he would have done differently and what he misses the most of the good years.

Here is a short list of what my uncle misses of his “good years”:

  1. Girlfriends: as long as my uncle was rich he always had an amazing touch with women. He maintained a bit of this touch even after he was not rich anymore but obviously now he cannot do with these girls all the things he did before. In particular, when he was rich he was traveling a lot with a series of girlfriends scattered among Europe. These trips started in the 70s and he still remembers amazing hotels in Capri, Venice, London, Prague, Budapest, Paris which he visited with these girls and made amazing memories with.
  2. Most of his friends: when he was rich he was surrounded with friends (particularly in Venice, Italy). My uncle was in particular friend of the late Emilio Vedova and his circle of artists of the Informal Waveat the Venice Biennale. He fondly remembers the fantastic adventures, dinners, anecdotes with these friends. Once he ran out of money, he slipped into depression, some of these friends died or had troubles with their families and thus the group dissolved. As far as I am aware, he does not have more than 1 or 2 friends now and is social activity is close to zero.
  3. Eating out: my uncle still knows by name basically all the most important restaurant in Italy. If I tell him that I will go to visit a new city, he invariably would tell me where to go and eat and what to order there. He was eating out all the time in probably the best restaurants in Italy and I am conscious he misses this dearly.
  4. Cars: my uncle always loved fast German cars. In 2002 he had an bad accident (a truck driver crashed on his car, almost killing him) and had to go through serious heart surgery. The doctors did not allow him to drive for almost 2 years after surgery due to some complications. Eventually, because of bad investment and drying up resources he had to sell his cars and now (happily) drives a 12 years old Renault Megane my parents gifted him a few months ago.
  5. Healthcare: my uncle cannot afford to go to dentist when a tooth is painful. He had to wait 16 months to have an hernia fixed as he cannot afford to go to a private doctor.
  6. His Persian carpets: when money started finishing, my uncle had to sell one by one all his amazing Persian carpets which he had at home in Venice. When only the last two carpets remained, my uncle gifted one to me and one to my parents rather than selling them for peanuts to loan-sharks.
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