Hindsight is 20/20, right?

That includes everything in life…including the big purchases you’ve made that you now think were totally silly.

But are they as bad as the decisions these folks on AskReddit made?

Check out their stories and see how you measure up…

1. Very expensive.

“A wedding.

My wife and I are still together and we’re great, but the wedding was a ridiculous cost that I wish we would have kept more of.

An expensive diamond ring, this is a trend I’d like to see die out completely as it was a diamond company who conceived the entire thing to begin with.”

2. Adds up.

“Impulse buying.

No matter how many times I try to stop, I end up with stuff I don’t need.

Not expensive things, just little purchases that add up over the years.”

3. Blew it.

“On one of those casino ships, I watched a guy walk up to a roulette table, put down $400, and lose it all on the first spin.

The guy looked 20 yo, and definitely looked like $400 was a huge amount of money for him. He sat in the corner for the rest of the three hours we were on the water.”

4. Bad for you!

“Fast food.

Overly expensive, usually unhealthy, and never very filling.”

5. That’s weird.

“So I bought a camel at an auction one time.

He was expensive but the damage he did around the farm was worse. Destructive, stinky creatures…

Looking back I probably should’ve spent my money on literally anything else.”

6. Feeling guilty.

“Medical bills.

I have chronic pain, and all the doctors know how to do is trial and error. I have spent tens of thousands of dollars on medical treatments that haven’t worked, and I’m still in pain a decade later.

I feel especially guilty now that I have kids.”

7. Don’t even remember.

“Honestly, just random junk.

I inherited about $350k from my dad back in 2008.

My wife and I went around house shopping. The intention was to pay cash for a house and cash for a car (we did pay cash for a car). By the time we found a house we liked, we only had $30k left, which was just enough to make the down payment and buy down points on the interest rate.

Funny thing is, I don’t even remember what I spent all that money on. Just random stupid s**t, I imagine: DVDs, concert tickets, video games, etc.”

8. What happened last night?

“Al**hol at bars. I never wake up feeling like “money well spent!”

Usually I wake up feeling like “when did we get a pet tiger?””

9. You’re insane.

“Dead & Co tickets.

Experiencing buyer’s remorse for spilling $920 each for two center floor seats 10 rows behind the GA pit at the Forum.

Ticketmaster dynamic pricing has replaced scalpers.”

10. The American Dream.


I left my career a year after being diagnosed with bipolar 2 and a sleeping disorder. The job was slowly k**ling me and turned me into an al**holic.

So now I’m living the American dream. Working paycheck to paycheck until some cataclysmic health issue or student loan debt wipes me out.”

11. I’d be in there every day!

“A swimming pool.

We never use the da**ed thing, it costs a fair amount of money to maintain and takes up most of my back yard.”

12. All bad news.

“My house. Seems like every day I’m finding something or other that is bad.

I’ve owned it for three years, replaced part of the sewer line in the basement due to it rusting out and leaking. Reinforced one of the basement walls as it is pushing inwards, $15k for this fix and it still leaks but it does seem like it stopped moving.

My upstairs need refinished, no HVAC on the second floor in ND during the winter is horrible. The kitchen and bathroom need complete remodels. The fence in my yard needs replacing and I need new retaining walls.

Some words of advice from my experience those looking to buy a house.

1 – Have a reputable home inspector perform an inspection beforehand. Mine missed a lot of the issues I’m now encountering which seem like that would have been easy finds for him.

2 – Avoid shopping if there is snow on the ground, try in the spring when everything is melting and there is a lot of ground water, especially if the house has a basement.

3 – Bring a friend or family member, someone who has no investment in the purchase. Have them check any and everything out. They will more than likely find something you aren’t seeing through all of your excitement and stress over buying a house.

Bonus suggestions – Look behind all of your vents to make sure they are actually attached to the port. Jiggle the power outlets, you might find that some of them aren’t actually properly installed in the wall and slide out. Open and close every window fully, nothing like trying to open a window during nice weather to find out the handle won’t actually turn and open it.”

Now it’s your turn.

What do you regret spending money on?

Talk to us in the comments and let us know!