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

People harmlessly give and receive a ton of little loans to friends & family all the time. It can be as minor as getting the first round of drinks or buying tickets to an event. I recently went in on renting a vehicle for a trip with two others, a few hundred dollars each. Someone has to float the cost, how else could you do it? OP’s lending is obviously extremely lopsided (for six years?!) but using ‘always’ and ‘never’ isn’t quite right, either.

I’m not sure OP is being ‘presumptuous’ based on what OP knows, but we definitely have limited information about the justification for saying the new job will or won’t take up all the person’s time/energy for awhile.

Related to that, twice OP’s salary? 40/80 or 160/320? That might also make some difference. If the ‘dream job’ is really high paying that could at once be an explanation why it seems more unfair that as of now the previously beholden friend doesn’t plan on compensatory hanging out at friend’s expense. And a possible aggravating factor (envy) why the situation makes OP feel so burned. That might be more true if a person making say 160 previously thought of themselves as absolutely successful and friend’s job makes it seem less so, as opposed to two sort of regular incomes (40k or 80k): both OK, one obviously higher, but neither anything to really brag about. Nor do people making $80k necessarily have a lot to throw around on minor expenses. A previously underemployed person might also be digging out of debt you don’t know about.

But aside from lack of info the basic jist of advice seems right to me. Wait and see if it’s permanent before concluding anything. Don’t get the guy’s wife involved. If things don’t change then quietly think less of the guy if you like, but move on.

I’d bet on a heapin’ helpin’ that.

I dunno OP. You’re no better or worse off right now than you were before friend got the good job. If you’re hurting for money now and need to tap his resources to square the friend debt AND address any of your immediate problems, that’s it’s whole thing and you’d be right to squeeze him some. But if his situation has changed for the better and this is just you being impatient for money and working out his finances in your head and feeling stiffed because you know his situation better than he does…well that’s something else entirely. Be patient. If he stiffs you, he was always going to and you’ve just misread him all these years.

Tl:dr past this bit of title.

Should I expect repayment from a friend…

No.

You can ask your friend, now that he’s employed with a job better than your own, when he’s going to start paying you back, but don’t count on it. He may surprise you, but don’t count on it.

The next time you guys go out, wait and see if he grabs the check, but don’t count on it.

I do agree with this over small amounts of money.

However a few times I’ve been asked for much larger sums (over $1,000) - in which case I requested that it be treated as an interest-free loan and that we put it in writing.
Only one person refused (and later he turned out not to be my friend.)

I agree. If I’m paying for someone to do something fun with me who couldn’t otherwise participate, they don’t owe me.

Unless you cared enough at the time to write up a contract, you were making a gift every time you paid for the evening out. You should never expect to see a cent of that money again.

I always think of it this way: it will all even out when you die.

If you actually kept track of all those $100 loans, then it’s entirely reasonable for you to tell him, “Well, I’m sad to hear that you’re so busy now. Let me know when you have time free. Oh, and also now that you’re pulling down a wage I’ll expect you to pay me back that $3400 you owe me. Say by this time next month? Thanks.”

At this point he’ll either 1) refuse, 2) agree, or 3) try to talk you down. For 1, I’d tell him casually that he’s never seeing a penny from me again, but I’d be happy to hang out from him the next time he’s free (dutch, of course). For 2 I’d accept it and tell him that I’d be happy to hang out from him the next time he’s free (and then wouldn’t offer to pay his part, but wouldn’t require him to pay for me). For 3 I’d let him talk me down to a more drawn-out payment plan, but anything less than that would be 1.

Money you spent while taking him out was your choice and not something you can expect repayment for. “Loans” you didn’t keep track of aren’t loans, they’re gifts you can’t expect repayment for either. And seriously, never give out a loan if you can’t be completely sanguine with not getting it back - be it a loan of a DvD or of twenty grand.

Whose suggestion was it to keep doing those things? Who made the plans?

I was in a similar situation with a friend where I kept paying for things, until he finally told me that it was making him uncomfortable, and he would rather do cheap/free things .

This.

I hate it when I’m on a financial low and my friends would insist we go to the movies, dinner or the arcades. It was even worst when they’d treat me and then I’d feel obligated to reciprocate the next time, which equals spending the money that I didn’t/really couldn’t afford to X2.

Want to hang out? Let’s watch movies at home or go out after dinner for coffee or a soft drink and just sit and talk. Going to the movies always seemed silly to me. You hang out for three hours and spend of that not talking, and the last half hour is about the movie!

Look, your friend’s probably intimidated by this new job. He’s got debts to start paying back now, maybe his wife’s saying “Time to rebuild the savings account!” And he’s afraid the job’s going to use up all his free time he used to have.

All of these are emotional reactions, not rational.

And in a few months, he’ll probably see that he does indeed have time for friends (including you, if you don’t alienate him before then), and money to start treating you or paying you back.

Reciprocation would mean that if the OP were ever financially strapped, his newly-solvent friend would cover costs on their evenings out together.

That’s how reciprocation in friendship works.

The arrangement described by the OP does not look to me like a loan with an expectation of repayment. The OP paid for their evenings out becuase he enjoyed his friend’s company, and he liked spending time and sharing experiences with him. That doesn’t give rise to any expectation of repayment between friends. Sure, the then-penniless friend was a beneficiary because he got the social benefits without the financial costs, but that’s because he was penniless, not because he had accepted a commitment to repay and had been assessed as creditworthy.

My thoughts having been in a similar situation as the OP. Invite him out a few times anyway, planning on paying like you had before. Place him in the situation where he has the opportunity to take the high road without forcing him. If he accepts and doesn’t offer to at least cover his portion at some point, you have your carved in stone answer.

In short, no.

I was wondering who Mark was hanging out with these days.

You’re Screwed. Sorry, Dude.

I’ll be your friend. Wanna go out for beer sometime?

I have been in very, very similar circumstances to you.

But I have always made it clear to my cash-strapped friend that there is a world of difference between me paying for a few drinks and tickets to a football match because I enjoy hanging out, and when he came to me for an actual cash loan.

There is absolutely no expectation for repayment of the hanging-out type cash. When he has been a little better off since, he has taken me out to dinner “as a tiny way of thanking you for being so good to me”.

The loan came with strict expectations on repayment schedule, which he has stuck to.

So, have you kept track of the “small loans of $100”? I think it’s completely reasonable just to ask him what his plans are for paying it back. But, as others have said, be prepared for the fact that you are not his only creditor.

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.

Try and leave room for him to surprise you. You may think he’s just walked off and left you, forgotten your financial support etc, etc. But it’s possible he just needs to really focus on his new job and making a success of it. And he may have other outstanding debts to repay before yours. Or other obligations you’re unaware of. Just give him time, and try to think positively that it will all work out, down the road. Keeping score, takes a lot of energy and robs you of calm in my experience.

Good Luck!

This is sad, but true.

Money has a way of un-grounding people.