So.... i was a student traveling abroad w/gf in hong kong. We decided to check out Macau for a day so we took a ferry. As the story goes, I majorly fucked up and I overspent the ammount needed to get the ferry back (~$100USD i think, only had about $45). So I took a gamble.... seriously. I went to a casino and bet everything we had in 1 go on a roullette table. All on black, we won (@$90 now), still not enough to get back. Again, all on black... we won again(@$180 now).

You would think i stopped here. At this point my GF was no longer pissed at me and more relieved but I said 'fuck it, we missed the ferry so lets pocket 100 and have fun with it... we are sleeping in the street tonight anyways'. So now we start at 50 and decide to try Sic Bo (another card/dice game). We are both pretty good at math so we though lets run this for as long as we can. We ended up leaving with a modest $4k USD or something, stayed in the nicest hotel suite, and just went hog wild until sunrise for us to catch the ferry. Good times.

I'm a miser so I've got a couple:

Carried a microwave by hand for an hour on transit rather than have it delivered for like $10.

Rushing to hike up a mountain before sunset rather than taking an $8 gondola ride, I survived but my buddy who was with me had a sore foot for the next week.

I ate ramen for almost every meal for like a month and the doctor said my sodium is off the charts and that I need to stop.

Bought a house so I could pay $1200 in mortgage toward my own investment instead of $2k a month into someone else’s pocket. Insane, I know

I quit smoking and saved the money every day until I had enough to buy a TV. Would have been a good way to incentivize myself to quit smoking and not crazy but I started smoking again immediately after buying the TV.

Ata canned sardines for a week.

By Wednesday I was beginning to make mistakes at work.

By Friday I had more mistakes in that day compared to 3 months of workday. I was having a hard time understanding instructions and documents.

I did it to save lunch money.

Steal

At college I walked to the nearest train station to pick up half smoked cigarette butts when I couldnt afford a pack of cigs (~10 km). At the end of the month usually. Me & my then boyfriend waited until like 2 am then walked the city to go through clothes & house items left besides the dumpsters. This was before covid and all that

Never paid for health insurance in the last 13 years. I still don't have it.

Left my socialist paradise hellhole country with my whole family, burning the little we had, risking our lives, just to be able to eat 3 meals a day.

Now we live a better life and all is better, much better than inside the leftist hellhole

I worked three jobs for a year straight with no days off.

Had a temporary promotion running for a vacuum in the store I worked at. Ran out of them, no New stock coming, but for a week we kept awkwardly repositioning this one show model. Until I just walked up to the boss and asked him if he'd at all mind if I took it home. Didn't have a charger, or a manual, or anything else for that matter. So one internet search later, I got the charger in the mail for about 40 bucks. Sure that's a lot for a charger, but it's all I paid for a vacuum that would've set me back 300 bucks or something.

Either that or a store that went bust where I bought a jacket. Still got it. Priced it down from 170 to 30 lol.

Besides that, hardly any social life so no going out, no drinking either, no smoking, no drugs. I do spend a bunch on old books though. Gotta have a vice right.

I spent my sophomore year in college eating nothing but oatmeal except for family dinners and holidays.

Maybe not that crazy, but I yanked a tooth that cracked after getting an estimate of $8,400 USD from the dentist.

As I’m considering travel for holidays in a couple of months, I remember trying to save money on a similar trip by using five states …

— starting in Massachusetts

— drive to airport in New Hampshire

— layover in ??DC??? (sorry, many years ago)

— fly to Toledo

— drive to Michigan

I became a minimalist, threw away some modern convinences, moved into a canvas tent, save everything/don't buy anything but the most essential necessities of life and pay for EVERYTHING out of pocket without ever taking debt or rent

Craziest as in the most profound or the craziest as in the most out-of-my-mind thing?