Fiancee's family has some good stories for this thread. Let me preface this by saying one of her aunts (out of several) ended up fairly mustachian-ish. They raised children on one salary and retired at 55 I want to say. Government job, pension, tsp.
On the other hand, there's her other aunt who is losing her house. Why? She didn't pay the mortgage for a couple years during the recession after she divorced her husband. After not paying for a couple years, she tried to refinance but wasn't qualified (what a shock!). Recently, someone bought it from the bank so she's supposed to be packing up to move. My fiancee has tried to help her pack, but she's doing nothing to pack/sell her stuff. She's in her fifties and completely f-ed.
Going with this theme, fiancee's brother and SIL have no money. They are going on trip after trip with their two kids, but complain about being broke. Until very recently, FMIL (future MIL) was paying for their medical insurance to the tune of double our rent. Did I mention they live in a McMansion with SIL's parents living there and paying for part of it? So a few days ago, fiancee's brother tells her that he paid off his credit card debt. I was surprised at the time. A couple days after that, I heard about the trips and put them together. Likely they took out a HELOC, paid off the plastic and then used the rest to go on trips.
Finally, FMIL. She and FFIL have had really good incomes for many years yet remain essentially broke. They are aging and are finally selling their business, which should be enough to pay off their debts with a bit left over. The bad news is that they have no savings and are going to have to live off of whatever is left after everything is sold plus SS. It's not gonna be pretty. The sad thing is, they should have done well, and part of why they are where they are is because they love to help people (insurance being an example).
SIL has told us that we should go out and do stuff. By that she meant eat out, go to the movies, or spend in general. This was after she heard we're frugal. She stopped after we took our trip to Canada, but it was annoying to hear it for several months...