What explains a friend who willingly makes plans, and then, consistently, stands you up without any notification (no text or call, just drops off the face of the Earth EVERY SINGLE TIME)?

Not a caring friend. Stop making plans with them. Next time say, "Let me check my calendar, I'll get back with you." Or say "I'll meet you there" and go alone.

Either way you'll be there alone.

I would not consider them a friend and would NEVER make plans with them again.

Dear Chet Elderson,

I will take a different tack here, because this might not be bad friendship...

I have a friend who is a hoarder, and we are close since 1966, long-term friendship! For some people, their minds just work in very different ways, and cannot change any more than eye color.

* * *

Anyway, in my case Molly DOES eventually show up, but she thinks within three hours of the appointed time is doing good... So I always arrive on time but with a book or other project, adapting to her.

In your situation, seems clear making plans is never going to work so maybe just find other ways to carry on the friendship on his terms...but def stop making these plans, find other ways for your friendship to flower, where it makes sense to the friend and he can succeed.

What explains it?? Enablement... Clearly.

It would be understandable to give 2nd .. Maybe even a 3rd chance (emphasis on "maybe").. IF (emphasis on "if")  this is a friend .. And I use the term to mean a real friend .. Not just someone you're friendly with .. Anything beyond that .. You have to ask "why would you bother?"

Someone who offers no appologies or explanations  and shows such  a level of disrespect is no "friend". By tolerating this behaviour you are enabling it. 

I'm playing devils advocate here ... I agree with everyone else ... But I'm really bad for making plans and breaking them. Sometimes I just say yes to things in the moment , cos it seems like a good idea at the time ... It's a woman's prerogative to change her mind. Cos I said so.  I always let someone know I'm cancelling though... Unless it was a Maybe.. Then I owe no explanation... That's cos I said so too. 

Happy's edit:  Pomme Head finally gets her pony! 

You know they may be lazy or just have bad time management that or they suck like everyone else said.

Considering you knew this person since highschool and "your best friend" is this something that suddenly started happening or is this a trait you didnt have the chance to learn till now,  since it started?

That is one thing I can not STAND is making plans and being stood up. Not many people have ever done that to me. And the ones who did, it really affected our relationship when it happened.

I prefer to be confronted straight away with the truth instead of misguided hope or expectancy. Sugar coating is one thing but not when you make plans with another person and affect their day just to avoid guilt.

Dont promise what you--cant. Simple as that. 

Time does change some people, they change their tastes, their likes, their jobs and who they choose to hang out with. If you do ever get to meet up maybe you need to decide whether you actually like him anymore.  When people don't see each other for a length of time they sometimes get more concerned about what they can actually talk about. Unless you meet up you are never going to know.

If this were me, I would not make any more plans with this friend because at this moment in time, it's just not in the cards for him to show up or to communicate with you that he's not going to be there.

If you want to continue to be his friend, then ask if you could bring dinner over one night to share. If you are friends with his wife, I would follow up with her to make sure they are going to be there.

Bring dinner, maybe some wine, and if the mood is right then you could ask about this habit of his saying YES when he means NO (no as in he doesn't really want to go, so he doesn't show up or call).

Stay only a couple of hours. When the evening is done, ask your friend and wife if they enjoyed the evening. If so, tell them that you would love to do it again with them and for them to let you know what works. When you communicate face-to-face, it's easier to read body language and study their faces when they answer, so you can see if there might be something else going on beneath the surface. Hope this helps.

People have different friends for different reasons. Unfortunately we sometimes put more importance on some friends than what they put on us.