I work with a guy who's in his mid-50s and has serious money issues. I used to hear him on the phone with his wife arguing about money all the time, and then one day he started talking and couldn't stop. I think he just needed to vent.
He had gotten divorced a long time ago, no kids from that marriage, so by the time he met his new wife he had some savings and owned a house, although I don't know how much equity he had in it. He met his second wife, who has twin daughters aged around 10 at the time, and they got married. By now, the daughters are both in their 20s and going to Georgetown law school.
He tells me that he's doing a cash out refi on the house to help pay bills, at an 11.5% mortgage rate because his credit sucks. His credit cards are all maxed out (don't know the total), hence the refi. Another reason he needs the money is to pay for two apartments for the daughters while they go to school. Wait, two apartments? Yes, they can't live together because they fight all the time...
So the refi goes through, and he shows up at work with a used Volvo (he paid $5000). He asks me what I think, and I tell him it's a nice car but could get expensive if something goes wrong. A few weeks later, he finds out the AC doesn't work, so he takes it to a Volvo dealer. $1800 to fix it.
While it's in the shop, he shows up to work in an old Ford Explorer. I asked if that was his wife's car. Oh no, that's our SUV that we keep for bad weather. I told him I noticed that a headlight had burned out...he takes it to the dealer.
It was like watching a train wreck in progress, and the worst part was that he knew it was nuts. He kept saying that once the girls were done with law school everything would be fine, but I couldn't see him ever digging out of the hole he was in.