A friend’s dad is very fond of saying, “The main mistake people make with communication is assuming it happened.”
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So younger son wants to weaponize the fact that his bro didn’t pay him. So much passive aggression all around. Do. Not. Triangulate. Your role is to model what a healthy relationship is.
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Passive aggressiveness is what I passed on saying, but I’m glad someone said it. 
I don’t have sons, but if this happened with my two (19 & 21 now) I would say something to the older brother like, “The nice thing to do would be to offer Younger Brother some money. I know a lot of people were offering to buy that painting.”
He probably won’t like it, but honestly if someone is giving you something that they ordinarily get paid for, such as a plumber friend/relation helping you install a new faucet or a brother who painted a really cool painting, you offer to pay. They can then counter with, “no it’s not necessary” or maybe, “well, let me give you a discount” or “okay if you insist, it’s $300”.
I wouldn’t say that you had a conversation with younger brother, though.
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Why not say that you spoke to the younger son? There’s too much talking around each other and not enough direct communication.
Now that I think about it, this does remind me of a situation involving my two sons. It’s too complicated to go into detail, but the older one owed the younger one several thousand dollars (it had to do with settling college accounts, which is why I was involved in the first place). The younger son asked his older brother on a couple of occasions for the money, but the older one kept putting him off. I stayed out of it until the younger one was rightly upset. Seeing how it was originally my money I asked ds1, “Are you planning on stiffing your brother?” He said, of course not. So I said then he needs to write that check ASAP. And he did.
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Did you say that you were talking on behalf of the younger son or did you just intervene as mom?
Well, he did ask his mom not to say anything, but I feel like if I told older brother I talked to younger brother then that starts to sound like I am relaying messages between the two, and a little bit like younger brother is telling mom on older sibling, ala “I’m gonna tell mom what you did”, which is not what I would want to project. I would want to treat them as the adults they are.
I would want it to be more like I’m just offering a little worldly parental advice to older brother, especially since apparently he is prone to take advantage when it’s easy to. I might include my plumbing help example. For example, I have often reminded my kids to offer friends who give them rides gas money. If the friend refuses that’s fine, but make the offer. Same deal with the painting, make the offer, and then let younger brother decide what to say.
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I can’t remember exactly what I said. For me, the bottom line was that we had talked about how this transaction was supposed to go down, literally since they were teens. Ds2 understood completely; ds1 kept acting like there was ambiguity. There was no ambiguity. None. But it showed how tight ds1 is around money, which we all knew, but it never occurred to me that he wouldn’t pay up when the time came. And, of course he would pay – he loves his brother and would never stiff him – but it was uncomfortable for everyone that he let this drag out for months and sometimes you just have to provide a kick in the pants to people who are slow to act. It kind of reminds me of how OP talks about her older son “taking advantage” and how if you don’t just confront an issue it can linger. I felt like it had lingered long enough and that ds2 had asked repeatedly about it. I reiterated AGAIN the expectation, explaining again how it was supposed to go down and that I expected it to go down just like that and soon.
Yes, you’re correct that younger brother said not to say anything. That might change things, but I don’t think I’d get in this situation because I wouldn’t agree to not say anything, especially if they have put me in the middle. If it were me, I would text both boys and say I feel caught in the middle and that they need to figure it out. How they do so is between them.
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I am not sure if I would stay out of it as this could cause a serious rift between them over something relatively trivial - the cost of the painting. You are already involved since the painter son complained to you. You wrote that the older brother had offered to pay in the past so not clear why he thought this painting would be free. OTOH, the younger son did not set a price or negotiate. I would be concerned about him using this in the future against his big brother and so willing to intervene to avoid that.
Could you say something to older son like “How much did you end up paying your brother for the painting”? Possibly adding “I know he had folks interested in buying it?”
Or straight up tell younger son he was wrong not to set a price and let brother know he wanted to be paid. And that using the lack of payment against brother in the future is a really bad idea, since he wasn’t clear payment was expected.
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This. I’m glad our family is an “open” one rather than a “keep secrets” one. I’ve seen the other type from my dad’s side and it only leads to a lot of hurt, almost always due to misunderstandings.
The quickest way to solve a problem is to acknowledge the problem and discuss it. Misunderstandings fall away, so many can be easily solved, and if not, then at least you know what the real problem is.
It’s not up to the OP to solve the issue - that’s on the sons - but it would be really good to pull the curtain back (nicely) and let the issue see the light instead of covering it up and letting it burn/grow.
Just because two people are adults doesn’t mean they always know what to do.
Personally, I wouldn’t even keep any secrets. I’d let both sons know what I know (separately to not start confrontation) and tell them they need to discuss it together to get a working solution. If oldest doesn’t have the money for the painting he should return it.
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Good points, but younger son specifically asked me not to mention his inner turmoil. I won’t. If I did, and it was found out…now there are serious trust issues and a feeling of betrayal. I must tread lightly.
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So…now that I know the conversation I feel more confident in what I did (with your help!). At this point, I need to back off. Younger son doesn’t want me to say anymore than I did. Oh yes…he even mentioned every time older son looks at the painting he’ll think of how he didn’t pay his brother.
I’m not saying anything more to older son as younger asked me not too. I have to honor that request to maintain a trustful relationship with him. I’ve tried to give him other ways to look at it and he did, which I think helped.
I find that parenting at different ages needs different skills. What I could do or say when they were little, teens, college age and now young adults is different. My personality is still the same and the way I deal with them is mostly the same , but I have to massage it a bit.
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Your desire to do the right thing or helpful thing comes from a place of love for them - that’s very clear. Nothing wrong with that. 
You’re a good mom. 
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This has become quite the complicated and fascinating post! It’s very interesting to see how opinions have evolved. Everyone here has valid pros and cons, but I sense, @conmama that there is a real risk here of long term damage to the sons’ relationships.
I do not agree with some other posters here. We are always going to be parents. I’m not going to withhold sound advice from my grown children just because they are adults. If I saw something occurring between my kids that might possibly cause a life long rift, I would speak up to BOTH kids.
It’s possible they won’t appreciate my meddling. But I would argue that it is worth the risk. It seems clear that older brother is taking some sort of advantage and younger brother already resents it.
I’ll wager everyone here knows someone or even IS someone who has seen family relationships ruined over what perhaps didn’t seem to be a huge deal at the time. Family is for life. I know a lot of people who really regret family misunderstandings and who wish they could go back and fix things.
My stepbrother once caused a big family argument. Eventually, my dad stepped in and basically told all four of us to stop behaving like toddlers. It was surprising that he intervened (sadly, it didn’t work out), but I admired my dad for doing it. He was right to have stepped in, even if it didn’t go as he would have liked. We still respected him.
ETA: Perhaps a good approach could be: “I’ve spoken to to both of you and I understand your miscommunication, but you would both benefit from discussing this further before it causes long term damage.”
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One of my favorite advice columnists is Carolyn Hax of the Washington Post. Just today, a reader wrote in, saying that her parents were constantly bugging her 21-year-old sister about who she was dating. The big sister wanted to help and tell the parents to back off. This is what Carolyn wrote:
<<<So, yes, you can be a huge help to your sister, by declining to join the cast of this shouldn’t-even-be-a-drama.
It’s a deceptively difficult role, to relinquish one’s role. You have to fight the very impulse that moved you to write this letter, the voice that’s telling you, “I want to help my sister,” and, “Someone needs to restrain my stepmother.”
But your sister needs to restrain your stepmother, and she needs to do it by helping herself.
If she were making a disastrous choice — if her boyfriend were abusive, say — then it would be your duty to get involved.
This situation, however, like most, isn’t extreme. It may be human nature to see life in terms of highs and lows, but the bulk of it, really, is just navigating the vast, annoyance-flecked stretches in between — without inflating them into dramas.>>>
I think Carolyn’s advice is applicable in the OP’s situation.
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Or–the sister telling her parents to back off might wake up the parents as to the damage they are doing to the other sister.
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I agree with Carolyn.
What the OP has essentially said in her most recent update is that Younger Son has asked her to not be a flying monkey (i.e., don’t talk to Older Son on his behalf). And OP is respecting that request.
Using a flying monkey is a very passive-aggressive and often manipulative technique and it can cause lots of issues. (flying monkey is a Wizard of Oz reference, btw)
As for the Older Son’s pattern of taking advantage, it’s kind of hard to know what that really means (because different people might have different definitions of that phrase) without examples. But generally speaking, if somebody is repeatedly taking advantage of somebody else, it’s up to the person who feels taken advantage of to speak up for themselves and tell the other person to back off.
Younger Son probably needs to work on how to set proper boundaries with Older Son. Depending on the person and the situation, sometimes trying to be subtle and hinting isn’t very successful. Sometimes with some people, you need to be as blunt as hitting them over the head with a frying pan.
So if Older Son really DID agree to pay Younger Son for the painting, it’s up to Younger Son to remind his brother of the agreement. It only takes something like “Hey, you know I’m still waiting for you to pay me for that painting…since you agreed to buy it, after all. Just a reminder in case you forgot.”
If Older Son has a pattern of pushing the boundaries w/Younger Son in order to try to get away with stuff, then it’ll be up to Younger Son to not let him get away with it. Even if Older Son makes a fuss about it, has an adult temper tantrum over it, yells at him over it, or whatever it is he does in order to ‘take advantage.’
People can only take advantage of you with your permission.
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We have different opinions because we all have different family dynamics. This is not a one size fits all solution issue. @conmama should read all the opinions and see where her family relationships fit in our expressed advice.
Within our immediate family there is very little drama. Three sibs get along quite well (well, not “perfect”) and it would be rare for their to be angst. Doesn’t mean there is never misunderstanding. We are big on communication and words and in OUR family, I think we’d lean towards a comment or two of we had this situation.
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Seeing a train wreck happening hardly means (to me) that I should stand back and watch it happen, then have lifelong complaints about it.
I’d be talking to the younger son first since he asked not to mention it, and I’d point blank (nicely) say why I would be doing what I would be doing.
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I looked up triangulation and found a good article about it. Here’s an excerpt:
<<<It is predictable that everyone will encounter triangulation in their family relationships at some point, whether as one of the dyad seeking stability or as the third party who is being put in the middle. If you find yourself involved in a triangle, it is helpful to ask yourself a series of questions in order to determine whether this triangle will ultimately be beneficial or harmful to the family system:
- Are both people in the original dyad jointly seeking the input of the triangulated member?
- Is the input of the triangulated member being brought back into the dyad itself for mutual discussion and consideration?
- Is the dyad openly and directly communicating with one another before, during, or after the triangulation occurs?
- Is everyone involved, including the third party, able to speak frankly and express their own emotions and opinions authentically?
If the answers to the above questions are yes, then the triangulation is likely to be of the normal type which necessarily occurs in families over time.
- Does any member of the triangle feel overly forced, pressured, stressed, blamed, or manipulated by the interaction?
- Does any member of the triangle feel as if he or she is not allowed to speak freely, express emotions, or ask for needs to be met?
- Is the triangulated member being pulled into an inappropriate role (such as a child being parentified or overly confided in by a parent)?
- Is this part of an ongoing pattern of interaction in which the original problems never seem to be resolved?
If the answers to the above questions are yes, then the triangulation may be the type that is unhealthy and dysfunctional in the overall family system.
If you find that unhealthy triangles are occurring in your family, there are steps you may take to counteract the negative effects of such triangles:
- A triangulated person can decide to step out of the middle by refusing to speak about the conflict with the involved members. The triangulated person may inform the two people in the dyad that he or she will continue to have a relationship with each of them that does not include taking a referee, peacemaker, or other inappropriate role.
- Encourage the original two-person dyad to speak to one another rather than projecting their conflict outward. Open, honest, and direct communication between family members is the most efficient antidote to dysfunction in families.
- If a triangle is still needed for the dyad to stabilize, encourage the two people to seek a professional mediator, counselor, or therapist. The professional will likely become triangulated, but can step into the triangle with a background of training and objectivity which will allow the professional to work from his or her triangulated position to help the dyad return to healthy functioning.>>>
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