I have two stories, both kind of similar in origin.
The first -

I was working as a waitress in a small country pub. One Friday evening most of the regulars left, and there was only around 15 or so people in the front bar. We were not far from calling “last drinks” closing for the night when in walked a bloke none of us had ever seen before. He yelled out “everyone put your money away, I’m shouting the bar for the rest of the night!”
We wondered if he was quite sane, but he insisted he knew what he was doing, and asked that the barman bring out every bottle of black sambuca in the storeroom, as that was what he wanted us all to drink.
After the first two rounds of sambuca shots for all present, the gentleman explained his predicament. He was from a semi-wealthy family, with a high paying job and was originally just passing through our “blink & you’ll miss it” town, when he received a phone call from his lawyer. His (about to be ex) girlfriend had suddenly run off with another fella, and at 6am the following morning their joint bank account would be frozen and all funds split evenly between the two. This was before the days of smart phones and internet banking, and as it was a Friday night, no banks were open. He knew his girlfriend was from a very poor background, and was currently unemployed so she would be looking to get as much money as possible. The only thing he could think to do was to drain the account as much as possible before 6am, and our pub was the only place of business he could find.
I don’t remember much of that night. There was a ridiculous amount of extremely expensive alcohol purchased by him and consumed by us all, given how willing we were to help him out. He booked the best room in the pub for himself to stay in, and paid for the rest of the rooms so nobody would have to drive. One thing I do remember very clearly is that the next day was around 45 degrees celsius (around 113F), making all our hangovers absolutely horrific. But I do hope that there was a lot less in the account than when he first walked in.

The second story is kinda along similar lines, and took place a year or so later.

I was visiting the newly purchased home of the publicans who were my employers in the first story. The house was immaculate, four bedrooms, large fully-enclosed outside entertaining area, landscaped yard. The house had a room set up as an at-home theatre, with a projector and a large screen; there was a wine cellar and a walk-in pantry almost as big as the huge kitchen. There was nothing this house was missing, other than perhaps a swimming pool. Good real estate as we know is all about location, location, location, and this property was a 1/4 acre corner block (in a time where block sizes are rapidly shrinking to a mere courtyard), and it was on the edge of what was at the time one of the hottest up and coming brand-new suburbs that was highly sought after. Basically, the couple (my former employers) who bought it should not have been able to afford it.
I asked how much they paid, to which I got a lot of laughter, and they told me that it cost them between $140-$150K. This was astonishing, as the property was clearly worth at least three times that. And then they told me ..
They were driving in the area looking at anything for sale, and in the front yard of this house was a clearly homemade ‘For Sale’ sign. They stopped & knocked on the door, a young bloke answered. He told them that his fiancee had skipped town with his best mate, and had told him to sell the house & she wanted half the proceeds. His parents had given them the house as an engagement present, so there was no mortgage, and he obviously had access to whatever finances he needed, whereas like in the previous story, the young lady was from a much lower socio-economic background. So he decided to sell the house privately and asked my friends to make an offer. Jokingly they went as low as possible, thinking he would scoff and tell them to bugger off; instead, he immediately said “done” and put his hand out to shake.

The moral of both stories is clearly don’t screw around on your partner if you think you stand to make a lot of money from their families’ fortunes, because you will end up with nothing.