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

Long story short, my best friend since college has been unemployed/underemployed for the past 6 years. As a result he never had much money with his family basically staying just above the water line, his wife is the primary breadwinner. We hang out once a week/once every two weeks and he basically admitted to me that he didn’t have much money to spend on frivolities so I was happy to just pay for stuff for him, meals, tickets to local attractions, movie passes, just stuff friends would normally do when hanging out except I picked up the bill every-time just because he was my friend and I didn’t mind since we were having fun. In addition I made him some small loans or about $100 or so each several times for help fixing various things around the house he never had the cash liquidity to fix on short notice.

So last month it turns out he finally got his dream job in his college career field, and now will actually start making double my annual salary as a result. Now my plan was to basically just have him pay for everything in return for the next few years and just have that be considered even. But now he literally told me that for the foreseeable future (maybe forever he mused) he will not be able to hang out with me anymore because of his new job taking over all his waking hours (somehow) and that it’s been good hanging out. I have no idea why suddenly working a 8 - 4pm job now means that he can never hang-out with me again but whatever.

If he tries to basically ditch this friendship out of nowhere, do I have a right to ask and expect to be paid back for everything I’ve done for him? Or is that just how friendships work? You may ask how I could get my money back if my friend abandons me but I’ve actually known his wife longer than him and she’s always been super reasonable and kind and apparently doesn’t know her husband has been mooching off me for so long, so if I have too I might email her about this situation if it comes to it.

He sounds like he used you a little bit but you allowed him to do it. I think it’s crossing a line to drag his wife into the middle of it though, this is between the two of you, it has nothing to do with her. If the guy just got the job he is probably a little stressed about it right now, give him a month or two and maybe he’ll come back around and want to hang out, if he never wants to hang out again or pay you back then you’ll know he was a prick, other than that there’s really nothing you can do about it, that just my opinion anyway.

Was there ever an agreement for your friend to pay all this back? You say your plan was for him to pay for everything for the next couple of years, did you let him know that was your plan?

Generally speaking, if you didn’t have an agreement with him to pay you back then you shouldn’t expect him to. If that is unpalatable for you then you should never have been paying for him in the first place.

That is not the kind of stuff that it’s realistic to expect be paid back for. Picking up the bill for movies and meals and making small loans of $100 isn’t worth even thinking about at all in the long term, and DEFINITELY not something to press him on unless it’s you who is now down and out and I mean truly down and out, in which case if he is a stand up guy he will cover you. As long as you are above water financially, just let it go, seriously.

If he’s too busy to hang out, or claims to be…whatever. Maintain occasional communication with him, be friendly but also give him some space. He may be able to help you in the future with something…be savvy and don’t burn the bridge.

Every time I gave him money he always said he’d pay me back when he got a job again.

By plan I basically meant an informal thing where now he would be the one paying for everything, I didn’t expect him to suddenly object knowing he was making a lot more money than me now.

I’d give him some time to adjust and see if he lives up to this promise. If he doesn’t, he’ll show that he’s a thoughtless friend, at best. Pressing him for the money would, at best, get you a little bit of money, at the cost of very significant stress. Not even close to worth it, IMO, barring some major emergency need for the money.

Yes that is how friendships work. In answer to your original question: Yes, you should expect some reciprocation in a friendship when you’ve been covering the tabs and the economics change the other way.

Your only mistake is your original assumption that this was a friendship. It was not, and he is not your friend.

As I tell my kids: Friends never need to track who pays for drinks, gas, or lunch. It will even out over time. If it doesn’t, they weren’t a friend, they were a freeloader. And you should walk away and never look back.

If you were really ‘happy to…’, you wouldn’t be having this conversation now.

I don’t think he owes you anything but gratitude. It would be nice, of course, for him to offer some form of reciprocity. You should give him room to do so on HIS timeline, and as HE chooses.

I think it’s childish and petty to seek monetary payback. “But I did this for you, because I’m a good person”, doesn’t really jive with, “Now you owe me! Pay up,”

(Mostly seemingly motivated by your ego being hurt he can’t hang with you so much any more!)

If you are expecting him to pay down every nickle and dime you “happily” paid on his behalf, then forget about it. Because without receipts, it is hard for him to even know how much he owes you.

But yes, it is reasonable to expect some reciprocation, even if it’s partially in the form of in-kind services.

I wouldn’t put a time frame on it though. Six years is generous enough, but a lot can happen over that time.

Neither a borrower nor a lender be - the first rule of friendships and money is, don’t ever ‘loan’ money with the expectation you will get it back. You will always be disappointed.

Money and friendships don’t mix. Accept that what you gave was a gift - it will only make you stew otherwise. And that is never worth it.

If he really just up and said now that he’s got a job he’s not planning on seeing you ever again then I don’t blame you for being totally pissed off with him.

And your plan to present him with the bill for things you’ve bought for him over the past six years is exactly the sort of plan people come up with when they’re royally pissed off -ie, a terrible one. Goes double for anything involving his wife.

If he’s getting set to ditch you then you already lost your money - you don’t need to throw your dignity after it. If he’s just temporarily being a giant doofus you’ll do better giving him time to realise that on his own

I was your friend for a long time. After college my bestie and I went down different paths but eventually, quite by accident, ended up settling down with our respective families near Denver. For over 15 years we would periodically set up a roughly semiannual goofin off day–shooting, movie, bowling, bar hopping, 14er conquering, whatever. He was making roughly 3-4 times my salary and I was dealing with loads of expenses and just a little bit less than enough money to get by. He always paid unless I had managed to find some money in the sofa cushions and could maybe pitch in or buy a round. He was cool about it. It was understood that money is just a vulgar necessity and the point of our getting together was to have a good time. And we both knew that if a body needed to be moved, there was a willing accomplice at hand. My fortunes have changed a lot in the past few years. During that transition I had to give extra focus to the career and family, and didn’t get out to play really at all. But I’m through all of that (for now! Life’s a MF) and he doesn’t get to pay anymore because I don’t let him. We still do the same sorts of stuff and have a good time, it’s just my wallet getting the workout these days.

I did address him always paying back when that was the thing. He shrugged it off and said it wasn’t a problem, said it was more important to him that I keep my household afloat and that blowing off some steam was a benefit for both of us. I honestly can’t say whether or not he was keeping score, but I don’t think he was. Now that I’m paying I know I’m not keeping score. There is more to our friendship than that. The ability to pay is, I think, a poor indicator of the quality of someone’s character–for that you need to see performance over time. A great deal of time. I would take a friend poor in money but rich in loyalty any day.

I’m always impressed with the quality of the thoughtful advice given on the dope. I think the main thing with your friend is to give the situation some time, like months. The money may not be pouring in yet, and there might be some bills to catch up on.

But thinking of myself, if I had gone through a rough time and taken small loans (paying for tickets is something else), I would immediately bring it up that I was looking to make good asap.

He showed you who he is, and that lesson cost you 6 years worth of checks. Move on, forget the money, and forget him.

If he’s now making substantially more money that you are, you will soon learn he’s an “ex friend” because you won’t fit in with the same socio-economic environment he’s now going to find himself in.

This thread could have been started by my wife about two of her younger siblings. While my wife and I are simply older “ordinary people” these siblings are now wealthy business owners and after years of mooching off her as their wealth has grown, now they have nothing to do with her, even going so far as to not invite her/us to their family weddings.

Money does things to people so you may as well just move on, chalk it up to a life experience and forget about it.

I think it would be best if you just considered the money as the cost for having fun in the moment. It was like paying for a ticket to a play. It was the price for the enjoyment that happened at that point in time. I don’t think you should expect to get paid back since you likely did not view the money that way at the time. However, you should ask to get repaid for all the house repair loans you made over the years. Come up with a list of those loans and ask him to pay back the total. But it’s probably best to just forget about the money you spent on dinners and stuff like that.

Sorry he’s blowing you off. That seems like a terrible thing for him to do considering all you did for him. If it’s any consolation, he’s not likely to have many true friends in his life if that’s how he treats people.

Never loan a friend money (I mean, outside of the occasional “I forgot my wallet” type situation). Give it to them, or no deal. A loan is a business arrangement, not one for friends, and it should be treated as such.

If you give a friend money to help them out in a tight situation, and they later get out of that situation and want to give money back to you, hey, that’s great. But as a gift, it’s their decision on that, not yours.

I would think that it must be very disappointing to discover that this person valued your friendship in a completely different way than you did.

My first question would be whether you have other friends to slide in an kind of take his place, or if the relationship is such that you hope he’ll come around and agree to start hanging out again.

Based on what you have written, I would probably conclude that his “I’ll get you back later!” comments in response to your gifts were empty platitudes. Most likely, I would write off all those nice things you did as gifts. If the guy isn’t a complete jerk, he should be making it up by doing nice things for you, not giving back the money that you’re out over all these years. Perhaps this needs to be explained to him if the friendship gets back on track. If he doesn’t get it, perhaps throwing in the ol’ grandmothers guilt: “I’ve really liked hanging out with you, even when I had to pay your share of going bowling (or whatever). I just don’t understand why our friendship is ending because I helped you pay to fix your sink last year, when you didn’t have the money. Should I not have done that?”

Then then you flip him both fingers and storm out.

Somebody who suddenly “has money” doesn’t mean they suddenly “have extra money”.
Even being un/under employed the guy seems like he was never able to live within his means and got used to hanging with you for leisure activities that he really couldn’t afford. Pretty sure he’s going to find plenty of things to spend his new found earnings on (hint-not you) and I wouldn’t be surprised to see him living beyond his means again.

One things that sounds a little… presumptuous, on the part of the OP, is the assumption that his friend’s new job and lack of time means he’s trying to dodge payback. How do we know that’s the case? How do you know his job isn’t going to be much worse than 8-4, or that he’s anticipating extra hours, or home chores, to make up for the fact his day is no longer his own?

If someone has been under employed for so long, then a full time job can be pretty daunting. You may find, once he’s got his feet under the table and realises life does go on when you’re working, that he will reappear, and your doubts about his miserly-ness are unfounded.

You’re thinking about the money, but he may not be - we’re not all always on the same page with these things. He may not know this is chewing away at you.

Maybe cut him some slack/time, eh?