I've got a story that I've thought of posting since this thread first started; it's downright depressing and I'll share it below.
One of my parents has been an over spender and person who lives the "grand" life since they first became an adult. They have forever chased the "next big windfall" and, surprisingly, they have always magically found one. My other parent has stories of this going back to my childhood - we're talking leaving the responsible parent with me for the weekend with no money, no transportation and barely any food while the over spending parent took off for some adventure that required lots of money. Needless to say, this marriage ended when I was young and I grew up with the responsible parent. The other parent moved cross-country multiple times and could never be depended upon to pay for child support ("because it was helping the responsible parent.")
Fast forward to late 1990s when larger than life parent met another wonderful, responsible person and they fell in love, got married. That new responsible person had a paid for home, investments, healthy retirement accounts and a great career. Very quickly my irresponsible parent convinced their new spouse to sell their previously owned home and they blew through the proceeds to professionally decorate the home they were living in together. Then new spouse's only living parent died and my stepparent inherited not insignificant but not huge amounts (200-300K.) Within five years they'd spent the inheritance, all the investments and all retirement accounts that were non-401K. Stepparent then changed jobs and (of course!) my fuckhead of an irresponsible parent convinced them to take out and spend the 401K from the former job. Along the way, they repeatedly did cash out refinances on their home in a VHCOL area and bam 2008 hit. Somehow they were able to keep said house but were always robbing Peter to pay Paul and keep up with the payments. My parent stopped working somewhere in those years and it left the stepparent to earn money to keep up with their financial obligations while my parent "managed the money."
Eventually stepparent got laid off and that's where it went even further downhill. Fortunately, they were able to short sell the house as they truly had no other money in the world to keep up with the payments. In a matter of months they blew through a mid five figure severance package and then unemployment ran out. They moved to a VLCOL place where another family member offered a lifetime lease on a lakefront property (with two houses), in exchange for payment of the property taxes after the first three years. Six years in I find out that they've never paid the property taxes over the three years in which they were responsible for them, so I offered to pay them to ensure they didn't lose this lifetime lease and get kicked to the curb.
Over the years my worthless parent has continued to spend every penny they have, plus run up all sorts of debt that they never even make a payment on. They repeatedly overdraw their account at the bank to the tune of $1,000 per month and when SS hits the account, they immediately skim the top $1,000 off the deposit just to bring their account back into the positive. On the day SS posts, my parent spends all day shopping on Amazon to find things they can buy and very quickly the cycle repeats itself all over again.
My stepparent is a wonderful person but for whatever reason is desperately afraid to confront my bully of a parent. In the meantime, they go to a job everyday (at nearly 70 years old) just to help with finances. It's such a sucky situation and I have no idea why they have stayed in the marriage for as long as they have.
My parent has asked repeatedly to borrow money over the years to cover overdrafts, pay for prescriptions, get the water bill current so they don't have the water turned off, blah blah blah. Between their two SS checks and my stepparent's paycheck, they are living on more money than my SO and I do on a monthly basis. Mind you, we make a hell of a lot more but in typical MMM fashion we LWBOM and save way more than we spend.
It's a miserable situation and it is devastating that my stepparent has allowed my parent to do this to them. I'll never understand how they could let it get to this point. I try to stay out of it and not let it be my concern but it's very hard when you see this kind of thing happen to people you love, at their own hand. We stopped helping financially long ago because we refuse to be the next victims of my parent's out of control spending, and we also know that it doesn't really help them at all; it just allows the situation to continue.
Once this parent is gone, we certainly plan to make sure the stepparent is well taken care of as they have no children or other family of their own to lean on. In the meantime, my stepparent continues to work and tells my parent that they will not be able to work forever but it seems to fall on deaf ears and the spending continues. This is by far the sorriest situation I've known of causing someone not to be able to retire.