Should I expect repayment from a friend for paying for everything over a 6 year period?

[asahi]

@Asuka

Thanks for the advice guys, I’m going to just let sleeping dogs lie.

To clarify, I wasn’t going to ask him for a check for literally every single taco I bought for him for the past 6 years, I was just going to ask for the loans I made him that were more than $75 that both me and him still remembered and there’s proof somewhere (for example, the fact his car has new tires I had paid for). Basically just ask for a lump sum of everything he said he would pay me back for. But now I’ll just see how things proceed from here.

If he wants to hang out, what you could do is tell him that you’re watching your budget and have to watch what you spend. See his reaction. He should offer to pay, IMO, considering how many times you’ve helped him. If he didn’t, I’d probably see that as a bad sign.

Having said that, you’re the only one who knows this person and what your friendship is all about. Maybe he’s good company and the fact that he owes you doesn’t matter. Only you can answer that question.

But for me, I judge people, even friends, based on their behavior. I judge them on what I see, not just what I want to see. Some behaviors are annoyances; others are more problematic. Each person has to decide for himself/herself what the boundaries are, and that really depends on your value system. I’m afraid nobody can really offer guidance there.

[MandaJo]

I’m confused about the timeline. Did it go:

You: Hey dude, now that you have a job, I’m gonna let you pick up the tab for a while.
Him: Actually, we won’t be hanging out much, I got a job!

or was it:

Him: Dude, I am so bummed that I won’t be able to see you nearly as much now that I have a job
You [thinking]: but when will you have the opportunity to pick up the tabs you so clearly need to pick up?

[zweisamkeit]

@MandaJo

I’m confused about the timeline. Did it go:

You: Hey dude, now that you have a job, I’m gonna let you pick up the tab for a while.
Him: Actually, we won’t be hanging out much, I got a job!

or was it:

Him: Dude, I am so bummed that I won’t be able to see you nearly as much now that I have a job
You [thinking]: but when will you have the opportunity to pick up the tabs you so clearly need to pick up?

That’s exactly what I was wondering.

[kanicbird]

While you may think he is making so much more then you now, it is not the same as before. Before he was unable to do those things - Basically you had ‘1’ he had ‘zero’, he was unable to do anything in the 1 ‘category’ on his own and doing so would be hurtful to him.

(without going into actual income levels I’m just saying that your income is 1 (unit), his was zero, but now is 2 units as you said his income is now twice yours)

Now you both can do those things for anything in the #1 category of stuff to do/buy ; you have 1 he has 2, so you both can foot your own.

If he was a stand u guy he would treat you to something in the ‘category’ 2 level sometimes however that is on him to offer, not you to ask.

[lingyi]

I had a friend that I lent money several times, adding up to several hundred dollars. He always said he would pay me back, but never did and I never expected him to. It was just a thing I did for him as a friend. The last time he mentioned it, he said: “I owe you over $300 don’t I?”. I said don’t worry about it. He never paid me a penny.

The twist to this is that while he made way more money than I did, the reason he was often short was because he would spend his money at the bar.* Once I had to pay his electric bill before his electricity was cut off. I told him the only reason I agreed to it was because of his wife. I didn’t want her to suffer because of him. If he was single, I wouldn’t have paid.

*Note: He wasn’t an alcoholic, so it wasn’t like I was supporting his habit. He’d go to hostess bars and spend hundreds of dollars in a night. So yeah, if anything I supported that habit to a small extent.