Why does my friend make the right moves in the dumbest ways possible?

Ok my best buddy is a dude I have known since I was in 7th grade, him and I were in youth group at our church as well as from the same school and neighborhood, we are both 30 now so its been many years. Over time though my friend has made some not very smooth moves while achieving/attempting the big prizes of life. He is married and they have a young son, but they only got married while their son was a toddler, though if he was that down for his now wife to have a kid why not marry ahead of time? The other thing is although he beat me into going to college first, he went to not one but THREE colleges across 6 years and must have had the worst advising ever since even with all those credits he just took a bunch of random dissimilar computer tech. courses and took out a crapload of student loans to attend for so long, and all for nothing as none of what he has pieces into a degree he could do with with. He has also been out of regular work for 2+ years save for the incidental work our other friend gets in which is very succeptable to customer demand. He seemed to want to impress the neighbors wherever he lived so a standard apartment wasn’t good enough for him, he had to spend nearly a mortgage payment’s worth of money living in primo ‘luxury’ apartments, only to have to bail in under a year and move himself, wife and son into his parent’s house only to do this again and back 3 or 4 more times. He also had a trusty old BMW that ran great until he bagged on the maintenance since it would have been expensive, until the neglected item made other systems get really bad as well and he ultimately donated his car to one of those give-us-your-car charities. His dad lets him borrow his pickup truck as he makes extra money to support his family on moving furniture but he left the GPS unit in the dash overnight just to have somebody break into his dad’s truck and steal it, though he doesn’t even file a police report robbing him of even getting insurance to help with the repairs and replacing of his stuff.

He is my best friend but moves like he does make me want to scream and shake the hell out of him at times. I try to politely offer him tips and advice on how to do certain things better but its tough to get my buddy to listen to advice, the closest I can manage is to suggest stuff he ignores, wait for him to screw things up bad and then he goes back the 2nd time around and nails it easily c/o my advice. We are both 30 I figure he would have picked up a trick or two by now.

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