Buying $50,000 worth of furniture and a $3,500 TV (which lowered to $3k a month after purchase, thank you black friday price matching) back in 2018 after buying a newly built house while I was the only one working in a household of 4. 

Thankfully paid it all off in 2 years - was maintaining the budget ever so closely until my wife started working later in 2020.

Wont make an investment like that...though we did accumulate $30,000 debt earlier this year (due to everything that happened from last year). 

Got it down to $12,000 left and expecting to clear that out by October of this year.

It is still there due to the Republicans. I would have paid it off if Biden kept his campaign promise.  $30,000 while still expensive, is a much more fair price than $50,000.

Not too crazy but in 2011 I bet 1400 euro on the Miami Heat (Lebron+Wade+Bosh) to win the NBA finals against Dallas Mavericks (Nowitzki). I didn't want to do it initially as I had my doubts but my then online friend talked me into it, he bet 3 times more.

I got arrested and thrown into a Chinese jail for one day they couldn't hold me past the evening because the US embassy was going to get involved.

I accepted being a sugar baby for a few days while I was on vacation in another city. I didn’t even need the money (the payment itself was kind of negligible, just a few bucks he give me to buy clothes with him); I just wanted to experience what it was like to be spoiled and taken care of, haha

I met him through a dating app he was alone in the city and wanted some company. He paid for the restaurants and the hotel (I had my own hotel booked, but since we met through the app, I ended up staying in his room). We even pretended to be a couple at a party

Looking back, it was probably a bit risky to sleep with someone I barely knew. I kinda regret it because although he said he was single I think he was probably married (no proof, just vibes). Deep down I always thought he was married, but I decided to get myself carried away by the moment

That's just the end of a story ... if you're not too embarrassed to share, what they hell did you do to land yourself in a Chinese pokey?