Bought a house in the late 90s and me and the Mrs had enough Sprint stock in the brokerage to sell and pay cash (we both worked there). I told her it had been on a good ride and we should use it to own our home free and clear. She put her foot down and insisted we needed to keep the stock and stay invested in the company we worked at. Six months later it had lost 95% of its value and never rebounded before the T-Mobile buy out.

Only silver lining is that shortly after that she backed out of all our financial decisions and left the brokerage and 401k account management to me.

My list is LONG and undistinguished.

In fact, I could count my good ones on one hand

Heavy equipment is my addiction so it’s a long list

My ex wife. Cost me tens of thousands of dollars on custody suits. Closer to $100k than $50k. And that was just the lawyer fee portion.

Actually.. best financial decision I ever made was emptying all my bank and retirement accounts to gain custody of my son and jettison the first wife. By far. Not even close.

In 1993 I bought two ribeye steaks and when I got home I remembered I had a buy one get one free coupon in my pocket.

Wife had a worn out 1992 Grand Am when we got married. Local dealer had a new 1999 Trans Am she thought she had to have. What POS car that was, we sold it in 2003 when we found out the kids booster seat wouldnt fit in the back seats. Too much purchase price, low quality, and horrible re sale.

Marriage.

No doubt, my worst financial decision was choosing to have kids, but I wouldn't trade it for the world.

100% correct when looked at from a macro point of view. I was just commenting in regards to short term, checks written, real estate lost....etc. May have cost me $$, but still the best decision I have ever made. By the grace of God, we did not have any children.

The occupation I chose versus the occupation i should have chosen. The first wife (loosely used terminology.)

Easy answer. First wife.

+1

I'm sure I've missed out on some stock investment type things but overall been a fairly pragmatic investor/spender of funds and have certainly "hit" on many more things than have "missed" on. Actually, I really wish I had purchased 300-500 acres back in 2008 in Young County instead of 70, that was for sure a missed opportunity I regret today.

Do not remember the exact year, in the mid 90's when the energy sector was very low, bought stocks of Harken Energy at .96 ¢ instead of small oil & mainly gas company that I cannot remember the name of that looked very interesting at $1.17 a share.

Stupid rationale on my part was Harkin was supposedly drilling a huge oil play in S. America and its website boasted that Governor Rino Bush was once a major stock holder. Well heck the upside on this has to be huge right? Nope Buffalo breath there was a reason Bush was a previous stock holder and not a current one at the time Sold it for $1.18 after it kept wobbling around between $1.15 & $1.23

That little mainly gas company I passed on got bought out by Cross Timbers/ XTO Oil Co. Shortly after that stock prices for Cross Timbers/XTO went through the roof because of their vast natural gas holdings and the soaring prices of natural gas , then Exxon Mobil bought XTO sending prices even higher.

How many dry holes did you drill? I only drilled one, but that was like lighting $7,000 on fire. Guy didn't know chit, apparently.

UGHHHHH

SO true!

Mine is 34 years old and still on the payroll.

Probably a toss-up between fishing, hunting, marriage, and kids. But my biggest expenditures bring me the most satisfaction👌

This!!!! The first one cost me quite a bit, the second (and last) one has been great.
On a side not. Never forget about what you have in the shared safety deposit box. OUCH!!!!!!!!!!!

The one on the left!!!! 20 Years of that mess

Mine would be stuff I didn't do more than stuff I have done...now my car habits are likely my biggest financial dumb thing but no regrats on those. But I've missed more deals I didn't pull the trigger on than ones that I've lost...I guess that's the fiscally conservative nature in me.

One, technically it wasn’t dry, <100 gpm, I moved location and next hole was 500gpm

X2
I spend more now but I can afford it now.
There was a time in my life that I didn’t control what I spent vs what I could afford. Not the kind of money that devastated me but I could of invested at that time instead of spending and it would of helped.

Joint account w/wife.
I've found it's much easier just to 'make more money' than it is to fix her, lol!

Lots of women issues in this thread, no doubt it was the woman's fault in most of not all of them. Was too much hunting ever the reason for any of these divorces?