When I started reading I thought maybe he was an addict and working thru some steps. When I got to this-"He gets indignant and says he's tired of the bullshit and should just cut me a check"-My thought changed.
You don't owe him squat. Any guilt you feel, let it go. This guy has probably been an asshole from the age 2. LOL write you a check.
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Now that was :-) I had not thought of that commercial in years.
Good stuff!
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If someone cheated me out of money or stole from me, they'd be out of my life permanently. Certainly no money and nothing of value would ever pass from me to them again.
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Yeah, the minute he tells you he'll cut you a deal while still owing you money...well, that's all you need to know about this dude. Don't hate him, it's not worth it. Just let him go.
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I don't hate him, that takes too much energy and people like that don't deserve the attention. I'm fairly certain that because I've seen him a few times, that he believed I was just 'cool' with the past and didn't expect him to be a man of his word. Or that I was such a 'good friend', that I would just let mistakes of the past go.

The analogy of losing trust in buckets and gaining it in drips is a good one. Going to take a whole lot of drips and I'm not going to get soaked again.
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If you want to get soaked Billay can hook you up with a squirter
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At the end of your life, you will be lucky to count your real friends on one hand.

This guy isn't one of those fingers.
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You can be polite but if you ever have any financial transaction with him again it's on you. Life's too short to hate but that doesn't mean you have to forgive or forget. Been in a deal or 2 like that myself and never saw many changes in the other person. Once a con/thief, always a con/thief. Just that now you are aware of problems and can prevent further loss.
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Thanks for all the great input; if I go back into this, it's my own choice and have only myself to be responsible for what happens.

After all, is money really that important? I have a grudge with my younger sister; i would do anything for her unless it had to do with money.

People change... I'm an idiot. We only get to go around once, IMO.

Maybe we would all be better of if we just let things go... Okay, I'm drunk...
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Some people are a blessing when they come into your life. Some are a blessing when they leave! Let it go. He's not your friend, he's a user.
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I'll echo others and wonder why you would even want to. If there is some sort of closer needed here, this is it. I personally never look back to someone who's betrayed or taken advantage of my friendship or generosity. It's swift and without explanation.
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KIRK, YOU SO CRAZY
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I'll go the other side of the argument.
You were how old, early 20's?
He took how much in change over that short period of time, $20 - $30?

If you have history you can talk about, and times can be good just being company, I say let that shit go man. Just don't put yourself in the position to pay his bills, right?
You can buy the guy a beer and not do the arithmetic or perform facial recognition to determine his 'feelings' about it, no? And if you don't have the cash to do so, just don't.
If he still wants to hang while you both go dutch, I say fuck it and see if there is genuine love for eachother that could still be of value to your life.
He himself may be operating from the shame and guilt of that early moment in time in your friendship, and to be called out like that over small change may be super hard especially if he feels like he brought a whole lot more than that to your life...
Has he picked you up and driven you places but not asked for gas money?
Has he had you over to his joint and offered you pretzels and beer while you hang? Maybe he feels like he's paid it back already but doesn't want to be a dick by pointing it out?

When I was young and a student and had no stash money, I didn't say no if someone else offered a toke or a bong. Actually, and cringeingly, many times I asked. For a couple years it seemed my friends all had money because they were out working while I could barely pay the car registration and rent.
Things have worked out ok for me in the long run, and I make sure to always turn up to my mates houses with flowers for the wife, or a spread of bagels and dips for a Sunday lunch, or pick up a tab at the Chinese restaurant for everyone at the table at least once a year. I want them to know I appreciated their willingness to share back in our young days, though I could tell at times it annoyed them I didn't have the cover money to see a live band or hit a bar tab hard so I could buy everyone a round...
TBH, caused me lots of shame. I fucking hated it.

So i try stupid hard to make things 'right' now, even when it seems over the top. Me and my best mate took a long weekend trip down to Tasmania last time I was in Oz and I booked the cabin we stayed in and refused to take a coin. You know, because if at the end of life and there's a tab, I don't want there to be any way some one says I took more than I gave.:-)

But maybe your buddy never got himself 'right', has never found a way to be professionally and financially successful, and he's still battling just to make it through an everyday day the rest of us mostly have covered.

I say call him up, see if hanging out is still fun or has passed it's nostalgic course. Maybe friendship now at your age (I'm 52 so I get it...) is more important than your honor at being stolen from so many years ago.

Life isn't always as clear as many here paint.

But if he fucks you again, well, there's always rat poison.:-)
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It's pretty clear that he is still screwing around. If he really wanted to make amends he would have just purchased you the CBD as partial repayment of the money he owes. He didn't, so he really isn't trying to do shit. At best, he is still sketchy and untrustworthy. He might even think he can rip you off again.

sorry, it sucks.

People are such assholes.
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This was my thought process. However, I don't borrow/steal from friends so my thought process is definitely different than his. My though process was that he can get this for me as a sign of good faith and instead, he is indignant when I say I'm not going to get into any financial transactions with him.

People do change; we were in our 20s at the time. My dad had just been diagnosed with lung cancer (he died less than 4 months later). A lot has changed and I have made other friends. None of whom ever did any of this kind of thing. So... keep him at arms length, let him rebuild some of the lost trust and just accept that this is what he is.
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