TL;DR: I want to give my brother some money with a few conditions on how it is spent but believe he is unlikely to realise that I seriously plan to enforce those conditions. How can I convey my seriousness to him?

I have an older brother whom I do/have gotten along well with for all of my life but is not so great with money/self control. Nothing so bad as having a gambling addiction, series of maxed out credit cards or anything of that sort, but as a particularly careful saver the difference made from his buying nice clothes, a modest car, a nice tv/speaker system, semi-regularly eating out and maintaining an enthusiastic social life is very clear. Obviously I have no problem with him or anyone buying these things, it is a personal decision of my own not to.

When I was 16 and he was 18 we both still lived with our parents and despite earning more than me, he would often ask to borrow small amounts of money. $20 here, $50 there and it accumulated to ~$500 before I started refusing to lend any more as it was a lot of money for me at the time. After two years of occasional nagging it was clear that I would never get that money back so I offered to forgive the loan if his old laptop I had been using for the past couple months (he paid $250 for it new) could be "mine" and that was the end of it. That is not to say I have never owed him. While studying at the university, I knew that whenever desperate I could sleep on the couch at his place and eat his food, use the shower, internet, get dropped off at a train station and he would not expect anything in return. And there were a fair number of times where I did exactly that.

Nowadays we each semi-regularly give/borrow/loan small amounts of money from each other but just recently he has mentioned in a more significant sense how he is running out of money and might have to borrow some from me. He recently lost his primary source of income and although there is no worry about his residency or physical health and well-being, the extra money for things like car maintenance, job searching, bills, general quality of life costs and the ability to buy things that will help in the long term would clearly be a massive help to him. Since I am aware of a number of these sorts of things coming up soon that are in his own best interest to buy, I am more than happy to give him up to $1000 which if he can return then great but I half expect, and am fully prepared, to never see that money again. However, he has bad spending habits and receiving enough money does not mean that he will buy these things that he needs. Based off my knowledge of his self control and past dealings with money I have no doubt that if I just gave him all the money he would carry on buying excessive items and then suddenly realise that he only bought half of the things he actually needed. I am happy to pay for his fuel, but not a $60 haircut and round of drinks for his friends. So when I do give him the money, I want to establish some strong conditions about what I am giving it to him for. When it is his own money, I am happy for him to spend it how he likes but since this is my own money, I feel it is similarly fair to spend it how I want.

After some thought the essential steps would be to:

  1. Separate the amount I give him into sections to limit the carelessness at which it can be spent.

  2. Tell him what the money is for, and establish a boundary that if it is spent on other things I will not give any more money.

  3. Follow through

Limit yes, but I am not prepared to only give minuscule amounts at a time or demand receipts/be asked and present for every purchase, that is far more of a strain on his time, my time and our relationship than I think its worth. Although I won't (and don't want to) know his specific purchases, if he were to for example spend the money going to a concert instead of fixing his car, both of these sorts of things I will know about anyway and can confidently use to enforce said rule. I do not want to be involved to the extent where I am basically be his financial arbiter and he would not want that either. The general understanding I already have of what he buys is more than enough since when it gets to the point where he has to ask, he would be well and truly out of money and I can be confident that 95% of what he buys would come from my money. 1 & 3 are self explanatory and do not think I will not have trouble with following through and enforcing my boundary. My question is about skills or techniques that can be used to express that I am absolutely serious when I initially talk to him in step 2.

For some context. There are a number of other issues that were expressed in a similar way, but we BOTH clearly acknowledge as not being serious. There are plenty of examples of this going both ways, from situations like "If there is so much as a scratch on my car I won't let you drive it to {$Best Friend}'s wedding." To things as trivial as "You aren't invited to dinner if you eat that last muffin." These cases are all empty threats and we both know it. Since using the car was known as the only feasible option left to travel to the wedding, and we both recognised it as something significant giving this over the top, false ultimatum was a way to express how much I didn't want it to be scratched and nothing more. If it had been scratched although I may have gotten mad, I am confident my brother would not have even have to ask to know that it was still fine to use the car when he needed. The muffin comment was a competitive joke, I immediately ate it in the face of his protests and yet there was no question about the validity of my invite.

So my worry is that even if I say "I will not give you any more money if you spend it on X" he may presume that I am just expressing that I don't want him to spend it on X rather than establishing a solid boundary of something that will actually happen. If I am able to properly convey to him how serious I am about the condition it will be vastly better for the both of us by helping with his spending, my peace of mind knowing what the money is going to and in the case where I actually do have to enforce the boundary at least he will be expecting it.

Asking for money is awkward and I assume he will try to finish the conversation as fast as humanly possible so a lengthy conversation about my thoughts may not work in this case...

What conversational skills and techniques can I use to quickly and effectively convey to my brother that I am setting a firm boundary rather than just expressing my hopes?

  • 1
    How old are you and your brother now?
    – user6818
    May 2, 2018 at 20:54
  • 1
    @Stacy 22 & 24 and he has so far only said that he will have to ask me for money. I aim to wait until he does ask me and yes, if I phrase it in a way that will clearly be a large pain then he may very well say "never mind". It is one of the reasons I do not want to consider the more time consuming options such as insisting on receipt gathering.
    – Jesse
    May 2, 2018 at 21:57
  • Can you explain in more detail why/how the relationship strain from buying stuff for him is too much - but cutting him off when he's in need (if he spends the money on luxuries and has nothing left for the essentials) isn't? Or are you willing to "dump him" in this case but not before? May 3, 2018 at 8:41
  • @AllTheKingsHorses Because he is not in desperate need, refusing to give him this favour may be inconvenient but its not that big of a deal for him. On the other hand, me having to personally buy it will take hours and hours of discussion, planning, shopping, and discussing again all in the context of something both of us hate. He will resent me for dragging it out and making a fuss and I will resent him for consuming my limited time. If I REALLY can not convey this boundary then we would both rather just not do it than go through this long and painful process.
    – Jesse
    May 3, 2018 at 9:49
  • The rule for friends is "if you loan money to a friend, be prepared to lose the money or to lose the friend". Obviously slightly different with a brother. The simple solution is to sign a legally binding contract. That demonstrates very clearly that you serious about getting the money back, and in the worst case it gives you the means.
    – gnasher729
    Feb 1, 2023 at 10:24

13 Answers 13


If you need to convey that this isn't another empty threat, then I suggest sitting down to a one-on-one and telling him exactly that.

You have many, many examples, from the sounds of it, to compare this to. Something along the lines of

Brother, I want to be absolutely clear that this isn't our usual "joking" seriousness about this kind of thing. This isn't like driving the car to Best Friend's wedding. I need to know that the money I loan you is not going to be spent on luxuries instead of necessities and you're going to get the things you need, absolutely need, to take care of yourself.

Comparing it to one of the empty threat moments may help cement that this is a different story. The last part, about needing to know, helps show that you are concerned for his well-being more than anything. You don't seem to mind that he has luxuries, and you don't seem to mind that he spends on himself. It reads to me as you are concerned about his well-being first and foremost.

My brother and I are in a similar situation. He's not so great at his spending habits, and it's caused him trouble in the past. Now, I'm not great either, but I've not missed a payment on my house or car. The worst I'm in danger of is not being able to buy new games when they come out, but I still have shelter, food, clothing, and a way to get to and from work.

When I started trying to help him with his finances, I did my best to make it clear I wasn't just gifting him money to do with as he pleased. Granted, I did take things a step further and check what he was spending it on, but so long as you point out how this is different from your usual gifting/sharing habits and empty threats, you shouldn't need to do this.

Now, if he wants to prove to you that he's spending wisely, I wouldn't tell him not to. Otherwise, it gives the impression that this is an empty threat, that you're not willing to be sure that he's doing what he said if he tries to show you. You don't have to ask for verification, but you should accept it if he offers it. You don't even have to actually check what he gives you, just accept it.

Comparing to past events to contrast the events and accepting proof should he offer it should help prove that you are serious about this situation.

As a side note, without verifying what he's buying, I'm not sure how you'll be able to enforce this rule. If you don't already have a solid plan for being sure he's spending money on what he said he did, I would be sure you have one or seriously reconsider not doing something to verify. Without a solid way to verify, this will turn into another empty threat, whatever you intend.

  • 1
    I really loved this answer. Exactly what I was hoping for, a great way to convey that this boundary is serious to my brother. So when I told him that I would not give him money if he spent it on _, I compared it to a previous contrary scenario and he understood me immediately. (also a small kudo's to Rainbacon's answer which was some additional helpful skills to keep in mind)
    – Jesse
    May 6, 2018 at 13:50

Offer to buy it for him. Yes, I understand you do not want to constantly be giving him 20$ here and 50$ there. You don't need to. You wrote that he mentioned multiple necessities you want to cover.

Let him make a list of what he wants. If you don't want to give away your plans yet, argue it is to help him calculate a budget. In fact, preferably try to do just that first. Go through the list and talk about how important each item is for him and how he could afford it. Then select items you deem important but too expensive for him to handle right now and offer to buy him those. You buy them, you can hand over the receipts later (for guarantees and other cases where he needs them).

If you do not want to "enable" him too much to spend his money on private luxuries instead of necessities, leave some of them to him to pay for. So you provide him with what you deem most important, he has to budget for the other things. And if something is left over, this is where his luxuries come from.

Budgeting is something some people have to be taught and it is not their fault, just unfortunate that school systems do not teach it.

EDIT: I feel the need to edit this because this answer seems controversial. While some people obviously upvoted it (and I even got a batch for it) others say (correctly) that it does not necessarily answer the question as formulated by OP. I want to address that. I read from the question that this is by far not the first occasion of this particular situation occurring. I also read that there is, in general, a very caring and nice relationship between the siblings. Sometimes the question we have on our tongue is not the question that bothers our mind. A caring sibling would want to help their brother long-term. And not hurt his feelings while doing so, because you cannot easily help a person that is mad at you. They want to provide them with necessities while making sure he does not spend the money on something else instead and then still lacks the necessities. One way to achieve that is saying it directly. Saying it in a worried way that makes clear you mean no harm. This often leads to the person feeling a short guilt but bounce back into their habits later anyway. Habits are habits. They don't just disappear. The other option is saying it in a stern way. It might spark conflict and lead to nothing at the end other than a damaged relationship. No change in habits either. There often is no way to change habits (your own or others) by just talking about it. Practical help is much more effective and usually also feels helpful to the receiver and is thus less offensive. They get the feeling that they receive help and love instead of discussions and blame. In my opinion this is an answer to the question. Answers are not always what you want to hear.

If OP is determined to just give their brother the money, I at least wanted to offer a non-offensive way of doing so. The boundaries are inherent. You don't always have to explain people boundaries. You set and enforce them. Preferably you offer very little weak points to get around them. This way they are clear, stable and not just "hot air" that can be blown away. You don't go there and put someone on a leash and tug and tug, you place a lake they cannot pass. The lake won't be blamed. You don't fight against a lake. But a leash will be questioned, chewed at and it will be prevalent always. The lake is only prevalent when you stand at its borders.

  • 1
    The point of the list is that it offers an option for him to figure out how to prioritize and budget his necessities. If you think this is a putting a strain on your time, fine, but he eventually needs to do this to get an overview over his needs/wishes and finances. I thought my emphasis on the teaching opportunity was clear.
    – skymningen
    May 2, 2018 at 14:39
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    Fair, and it may indeed be a solid teaching opportunity which is always a positive I suppose, but that is not the goal of my question. Since it is based around something I explicitly said was unwanted, I think some extra explanation about why it is actually the best solution for my question is still necessary
    – Jesse
    May 2, 2018 at 15:11
  • 4
    This isn't answering the OP's question of "What conversational skills and techniques can I use to quickly and effectively convey to my brother that I am setting a firm boundary rather than just expressing my hopes?" instead, you're telling them how to give them the money. How does this express the seriousness of their conditions? May 2, 2018 at 15:33
  • 3
    @VioletFlare - I think 'cause this is trying to answer like this is an XY Problem.
    – Malady
    May 2, 2018 at 18:43
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    @VioletFlare OP explicitly stated that they want to give their brother the money. And that there is a continuous problem with their brothers spending habits and that's why they are worried and want to set boundaries. I just tried to be helpful and mention that helping them change their spending habit and not just give him money, but give him the specific things he needs instead would a) solve the problem with the boundaries and b) help solve the underlying problem long time while c) not hurt the relationship but instead add a "big brother cares and teaches" thing to it.
    – skymningen
    May 3, 2018 at 6:18

If you want to convey something is serious, it always helps to put it in written form and have it signed.

It is your money so you can just state your conditions and put them in a small contract. This does not have to be a real, enforceable legal thing - just a "memorandum of understanding". He can then decide if he wants to take it and sign accordingly or not.

This makes it really clear that you are serious. It helps both of you to:

  1. Clearly communicate the rules of this transaction
  2. Remember those rules in retrospect after a certain time (when he asks you for more money, or you have a discussion about what was agreed).
  3. Give it a touch of seriousness. (If you want, you could also introduce a penalty for not following the rules)

Be warned however, if you think you can somehow educate him by giving him money and control his spending in return. This has great potential of stressing your relationship.

Other options would be:

  • Just give him a private loan (also with signed contract and repayment terms)
  • Buy the things he needs (and you approve of) and give them to him as a gift.

Background: I have personally made good experiences in the past with writing things down when you mix money and friendship/family, as soon as things get a little complicated. I have also seen otherwise with transactions that where made in good faith but not written down.


It may come across as initially harsh, but instead of gifting him an arbitrary amount like $1000, have a one-to-one (but fairly casual) discussion about what he is planning to use the money on and exactly how much he needs. Then give him that amount.

From reading the longer portion of your post, it seems like your brother has not learned to curb his spending habits when times are tough. Openly expressing that you have doubts about what he will spend the money on looks like it will likely cause a falling out. Instead, discussing what he needs it for will help you emphasise your desire that it goes towards something helpful rather than a 'luxury'. If he says it's for a haircut, discuss what alternatives there are to his usual top-of-the-range $60 dos. It's your money you are giving up, so it would not be unreasonable to do a bit of digging and find a place that would get it done for $20 instead, just as an example.

This also allows you the chance to emphasise that you cannot/will not lend any more until a later time. Have that boundary be established except in really dire emergencies. If you lend him $60 for a haircut and groceries but it all goes to his haircut, that was his own doing and cannot be faulted to you. This will help him realise the seriousness behind your intentions.

  • 1
    I said I was not willing to discuss and give him just minuscule amounts at a time. (I was thinking groups of $100-$200). The things he needs to buy are small, numerous and vary significantly. We both want to limit the time consuming and awkward discussion that this would require. If you want to suggest this solution anyway you will need to give some extra explanation as to why it is a solid solution despite my reasons against it
    – Jesse
    May 2, 2018 at 12:12
  • It reads as if your brother will not believe you are being serious if you are any less strict with him. How has he responded when asked to discuss other genuinely serious (not money) issues in the past?
    – user8671
    May 2, 2018 at 12:31
  • 1
    I have talked often about serious things with my brother and he easily understands their serious nature (e.g. talking about people close to us passing). I have not yet ever had to detail for him an actual rule and consequence before, only hopes and fake-consequences, which is why I was asking about communication skills to help convey that I will actually be following through this time.
    – Jesse
    May 2, 2018 at 12:42

You've said that this money is to help him pay for certain things that are coming up, given that he's lost his source of income. You can't easily enforce that he spends the money on those things without demanding receipts, going with him to buy them, or various other things that will make you both feel like you're acting as his parent or minder, which is only going to inconvenience you and make him feel distrusted and resentful. A better approach is to help him to change his behaviour.

State your intention

The first step is to give him the correct amount of money to cover the thing that you intend to pay for, with little or no extra. When you give him the money, tell him this:

"Here's $700 - that should cover this month's bills and the service on your car next week, right?"

This makes it very obvious that your intention is for the money to be spent on those things. If he comes back to you sometime later and says "hey, I can't afford my car's service tomorrow - could I borrow some money?" then you can say to him "I already gave you the money for that" and politely but firmly refuse to give him any more.

You don't have to be this prescriptive, of course. You could say something like this:

"Here, this should see you through to the end of the month, right?"

This leaves it more open, but makes it very clear how long you expect the money to last. As with the first example, if he comes back a few days later and asks to borrow some money, you can say "I already gave you some money, and you agreed it would last til the end of the month, and that's still a week away", and politely but firmly refuse to give him any more.

In both cases, you've made it clear up front that the money is earmarked for something. If you feel it's necessary, you could briefly reiterate as you actually hand it over "just remember, this is for your car payment" or "just so we're clear, this will have to last you til next Friday" or whatever limitation you stated originally. The repetition should make it obvious that this isn't just a casual comment or suggestion.

Reiterate and reinforce

Beside that, the best way to make someone understand that you're serious about an ultimatum is to demonstrate a track record of actually keeping to it. If he comes back asking for more money, remind him of the limitation that you stated originally, point out that it's not your fault if he chose to spend the money on a purpose other than what you meant it for, and refuse to give him any more until the next time. If you said it's for his car payment, then next time a car payment is due, you can give him some money for that. If you said it'll have to last til the end of the month, then on the 1st of next month, you can give him some more. This time, however, hopefully he'll remember what happened last time, and spend it more wisely.

You said that there are several things you want to help him out with, so you can make use of this, and give him the money for one thing at a time, giving him plenty of opportunities to learn that you're serious about your restrictions before the next one comes around.

Help him break the habit gradually

If you feel that his frivolous spending might be a hard habit for him to break, and you can spare the cash, then you could start out by giving him a little more than he needs initially, and then slowly shaving down the extra. This gives him some leeway at first, so that if he goes out and spends a little extra here and there it still leaves him with enough for the important payments, but as time goes by and he gets used to living on a tighter budget you'd expect him to get better at curbing his spending, so you start giving him amounts closer to the exact value of the payment in the hope that he's learned to budget a little better and will spend it more wisely.


Money does not work that way.

If you gift him money, then it is his to spend. There is no good way to change that. Sure, you can sit down, make written contracts etc. etc., and when the mood strikes him he can still spend it on a car. Stepping around these issues just brings tension, and eventually hurts everybody.

My policy on lending money, both with friends, larger family, and even my own children, is this: I gift money. I deny money. But I will not lend money, ever. Period.

He recently lost his primary source of income and although there is no worry about his residency or physical health and wellbeing, the extra money for things like car maintenance, job searching, bills, general quality of life costs and the ability to buy things that will help in the long term would clearly be a massive help to him.

No, that would not be a massive help to him. You said there is no risk that he is losing the roof above his head, or that he gets ill without being able to go to a doctor. That's done for, then. All you will do by lending him money is to delay the inevitable. He will have a nice cushion, he may feel little pressure to find a new job, and will most definitely spend the money on optional things.

So, I'd suggest this approach:

  • Decide how much money you can give him without it hurting you; under the premise that you have no idea what he does with it, and that you will not get it back. Give him the money. Make it utmost clear that it is a gift, not a loan. Do not by any means put any boundaries around what he can do with the money. Wish him good luck with it, and make sure he knows that he can do as he pleases.
  • When he asks for money next time, ... repeat the decision process. Your own situation may have changed. His may have changed. Your mood may have changed.

Remember from the beginning of the answer, that there are only two things that can happen: either you give him money. Or you do not give him money. This means, each time he asks, you decide anew if and how much you want to give (gift! not lend).

He has no power over you. He cannot argue "you can give me more because I will return it next month". He cannot argue "you have to give it to me because I will die otherwise" (if he really needs anything that is of life-and-death importance, e.g. a hospital visit, you might chose to buy it for him; in this case do not give him the money, but the item).

My experience with this approach:

  • People with decency will stop asking for money. Asking for a gift is much more severe than asking for a loan.
  • People without decency may keep asking, but as you have clear thoughts about all of this, at some point your internal resolution will switch to "enough is enough" and that's it. Because you can, on the one hand, give freely, the decision to not give anymore is also much easier for you (it is your decision alone, there is nothing to discuss with the receiver).
  • It helps to be very transparent about this. The interpersonal part of the answer is to explain to him what you will do, in the future (i.e., that your money is a gift, that he can do with it what he wants, that you are done with the childish games, and that you may change your opinion anytime).

Best of luck to you and your brother!


Ask him.

Before you provide money, ask him if he feels he really can spend it well. If he doesn't agree that he could improve in this area, you have no choice but to give small amounts at a time or get proof of what it was used for.

Assuming he agrees that he could really improve in this area, ask him what the best way is for him to be held accountable for it. Ask him what he is willing for you to do for both of you to know that this is working out. Ask him how much he feels he really could be trusted with at a time. Again if he really feels that he could handle it all (and you don't) or he feels that he needs small amounts doled out to him, then you are back to that being your only option.

Then, ask him how often you should talk about this issue and schedule a follow up time to do it. In all of these steps, he has either bought into the idea of being honest with you on what is happening with it, or you can know for sure that he can't handle it. You have a firm course either way.

You can then make this less of a "father/son" thing and more of a "brother/brother" thing if you ask him what he feels you should improve on. Then, you also work on that. The two of you will be improving each other.

All of this boils down to creating an accountability partner. Google books on the subject and you may have a solution to your situation.


One skill that can help you convey your seriousness is sustained eye contact

Making consistent eye contact will help you establish assertiveness and dominance in your conversation. A number of studies have shown this.

From the source:

According to a study from the Idiap Research Institute, eye contact shows a person's social hierarchy and dominance in a conversation.


Body language expert Lillian Glass notes the importance of eye contact in her book "The Body Language Advantage." Glass says that breaking eye contact not only suggests submissiveness but that "when eye contact is maintained, it signifies control or power over a situation and establishes dominance."

When you tell him the conditions under which you will give him the money, make and hold eye contact with him. Doing this (especially on the second condition) will help you show that you are serious about what you are saying.

Another skill that you can use to convey that you are serious is tone of voice.

The tone of your voice carries a lot of meaning whether you intend it to or not. Knowing this, you can select your tone in order to signify that you mean business. There are a few things you can do to give your voice a serious tone.

  • Speak matter-of-factly
    • Saying things like "you will spend the money on" instead of "you should spend the money on"
  • Place emphasis on the actions
    • "You will spend the money on [x]" and "I will not give you anymore
  • Keep the pitch of your voice consistent

Doing these things will give your voice a tone that emphasizes that what you have said is definitive.


Very often here on IPS we try to suggest the softest approach to conveying a message - the method that isn't going to put somebody on the defensive or damage a relationship. Those aims are still important to you here, but to convey seriousness as you have asked it isn't a soft approach that you need. You need to be tough but at the same time show your genuine concern for your brother.

What you say to him shouldn't dictate how he lives his life or specifically what he does with his money. However it is perfectly reasonable to be involved in what he wants to do with your money, so you should limit your enquiries to that.

I'm trying to avoid giving financial advice because that isn't what this question is all about, but it might help your case and potentially communicate to your brother that he isn't being smart with his money if you had a clear financial plan for yourself. Let's say for example that you were buying a property. You may have the money that he is asking for, but it is already put aside for a specific purpose. He probably wouldn't react well if you told him that he should be thinking about buying a property instead of wasting his money, but if he sees that you are managing to do so because you manage your money better than he does, this might just give him the jolt he needs. I'm not saying you need to buy a property! This is just an example - but if you can already see that he isn't managing his money well and isn't planning for the future then perhaps there is a similar way you can "lead by example". You're going to have a hard time helping him manage his money better if you don't have a clear plan of your own, because you can neither tell him a better way or show him one.

So, assuming you have put some thought into what you want to do with your own money, when he asks you for the loan you could say:

I can loan you the money you're asking for right now. But I am concerned because I may not be able to loan you any more in the future. You see I'm [buying a house / buying a car / taking out a pension / saving to get married / whatever!] so my money is going to be spoken for. We've always helped each other out in the past and I want to help you now - but as this may be the last time I can help, please let me help you manage the money.

I think this is a firm but fair approach that has a good chance of appealing to him to readdress his own attitude to money. You aren't telling him that he's been stupid with his money, you're not refusing to help him, and indirectly you are showing him a better way - when he sees that his younger sibling is able to budget for something worthwhile it should hopefully make him realise he ought be able to achieve the same.


  1. Agree what help he needs to become financially independent again (car repair, paying off debt, whatever).
  2. Agree the most cost-effective way to meet those requirements.
  3. Tell him the limit you can loan (if what he is asking for exceeds your limit). Don't just give him $1000 if he doesn't need it.
  4. Tell him that you will pay those bills directly, if possible.
  5. Only give him cash to spend as he pleases if he needs money for day to day essentials like food. Wherever possible just pay the expense for him.

With regards to his bad spending habits I will just pass on some very general financial advice that may really help during your discussion. Get him to examine all of his outgoings - any monthly or weekly costs - and make a budget. When someone sees how much they are spending needlessly it can be a shock. For example $2 on a coffee every morning on the way to work adds up to over $500 a year, which is half of what you are loaning him. Saving money is better than earning it because when you think about it you'd have to earn something like $750 and then pay tax to have $500 in your hand; whereas when you save yourself $500 you get to keep every bit of it because you've already paid tax! Simple reasoning like this can really change the way a person views money.

All the best!


Since both you and your brother live with your parents, you could get them semi-involved in handing him the money and conditions under which it is supposed to be used when they are around. A possible occasion might be just after dinner. Having witnesses is a good way of ensuring something gets done as it applies some sort of peer pressure.

Remember that you cannot change people. You can make it appealing to them to change themselves though. Demanding receipts/invoices that you can pay for him in hope it is as bothersome for him as it is for you might be a valid solution but you might find better ways to incentivize a change of behaviour.

Maybe your brother doesn't even realize his way of life being the cause of his financial troubles, but on the other hand you might miss something, too.

You could start such a conversation by getting his point of view as of why he ran out of money. If he figures and confirms your opinion of his spendings being out of proportion you can propose making a plan on why and what for to spend the amount youre willing to give.

It is important to rather listen to what he is saying than waiting for a catching point to get your idea across though. If he is not "ready" for your help you need to accept that. If you still want to help you could use the excess money you wanted to spare and donate it to your parents for their expenses on providing a bed for him.

Doing so openly (Your parents and brother both know of the reasons on why you'd give the money to them rather than to him directly) could shift his opinion but also bears the risk of guilt-tripping. Doing so without your brother knowing might at least help your conciousness.

  • i edited the answer, please let me know whether it makes sense now
    – Marcus
    May 2, 2018 at 14:19
  • Thanks, the edit helps and I think it makes fine sense :) however I don't think it covers what my goal actually is. I am not trying to get him to change, I want him to understand that I will be enforcing the conditions around my money this time.
    – Jesse
    May 2, 2018 at 14:27

If I'm reading this correctly:

Since I am aware of a number of these sorts of things coming up soon that are in his own best interest to buy

...it sounds like you know a number of specific expenses that are coming up for your brother that will be difficult to afford, but helpful if not outright necessary.

My suggestion is to list those items out, and then tell your brother that you are offering to pay for those specific expenses.

The reason for this is that it may be impossible to "give" him money, and then tell him that its not truly his to spend as he sees fit, without causing offense (I say "may" because individual personality and culture plays heavily into this, and some people are less likely to consider that inappropriate).

By offering to cover specific necessary expenses, you minimize the risk of his being offended by conditions of your assistance, while allowing you to be 100% confident that you won't be given cause to regret trusting him to spend the money they way you think he should.


In your question, "quickly" and "effectively" might be difficult to achieve at the same time. I think you are asking for a practical thing you can say, or way of saying it, that will convey a clear idea and assure that you both have shared meaning regarding that idea, and then you move on, confident that he will follow your terms and then return the money promptly. But as you explain, you have a fair amount of evidence that contradicts the likelihood of this type of shared meaning.

I would begin with a very clear statement (it does seem like you and your brother have a well-established honesty, so he can probably handle it), but you may need to follow that by taking a little more time to explain why you are concerned. This question is being asked in "interpersonal communication" and in that context you need to consider your relationship, and the way that relationship is influenced by the communication process.

On one hand, you want your brother to be responsible with the money you lend him (practical wish), but you are asking this question here because you do not trust him to do so (relationship issue). To keep this simple, if you want a loved one to change their behavior, for the sake of your ongoing relationship, sometimes you need to meta-communicate -- i.e.:

I honestly am a little worried about giving you this money because I don't think you always make the best decisions. I want to trust you. If you can agree to my terms and return the money it will really mean a lot to me.

You just have to be willing to create a little conflict to get to the heart of what this is really about. Again, my sense from the context you provide makes me think you two can handle it.

Adding this based on your message: I think I would still suggest this as a way of conveying your seriousness in the conditions. I know I lean toward the relationship side of things in my thinking, but my belief is that by sharing your own idea of how this impacts your relationship will help him understand why you are setting the conditions. It helps provide context, and conveys that you have really put some thought into it.


Most of the answers to your delightfully interesting question revolve around the dialogue with your brother but I think there is profit in clarifying your internal position.

Whenever we deem the actions of another unacceptable, we have judged that person in large or small ways. That judgement eventually comes out in our language and hinders the relationship.

I recommend either letting your notions of right and wrong go completely and let a gift be a gift. That will bring you the greatest freedom and clarity in talking with your brother or if that is not acceptable, address the issue head-on but stick to the specifics, asking him about what he thinks of his choice of purchases and refer to the plethora of advice above.

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