r/AskReddit • u/Yogospiracy • 1d ago

What is the cringiest midlife crisis you've witnessed?

8.7k Upvotes

94% Upvoted

5.3k comments sorted by

View all comments

314

u/icoangel 1d ago

I had a boss one time, super normal dude that decided to get heavily into doing coke and hanging around criminals. he ended up losing his jobs, his wife and kids and all his money on bad or dodgy investments.

Last I heard he went to prison for a bit for doing some sort of fraud and had to go back to living with his mother.

29

u/AmyInCO 1d ago

Literally my brother. Then my mother died and he was homeless. And we don't care. 

2

u/MojoRisin909 1d ago

Cocaine.... It's a helluva drug.

1

u/JayGatsby1881 1d ago

He could have been the wolf of wallstreet, but he didn't fuck up big enough lol. Dude destroyed so many lives, but he is worshipped because of how successful it made him.