Thank you all again for sharing your thoughts. It has been very helpful to hear your reactions and opinions. I know I was only able to give you limited information to work with, but trying your advice on for size, my youngest brother and I were able to reach a decision that I think balances the conflicting feelings we have been having.

First, I would love to “teach [City brother] how to fish,” as timwalsh300 suggested, but unfortunately I know that he is not open to hearing advice from me or anyone else at this stage, and his current financial plan is simply to keep looking for work and “who knows what the future holds.” So, that’s a strike against him. Also, until this recent news of all the money being gone, everyone in my family had thought he’d matured (somewhat) over the last few years and demonstrated much more focus on his studies and career, so I would have said he is “climbing out of a hole,” as Bishon Frise described it. But now (especially since talking to him again) I see him as balanced on the precipice of becoming a “drain circler” as DoingHomework assessed. (That was a very good point to highlight his failure to repay the first $500 how he’d promised in favor of keeping it to use on himself. I also was struck by how accurate I think your read of City brother is).

In the end, youngest brother and I have decided to loan City brother $1,000 (above the initial $500) because he is, after all, our brother and to show him a little support for a step towards his dreams (even though we’re privately screaming that it was all his fault that the money is all gone!). As Bishon Frise suggested, we told him that that is everything we are willing to offer and he cannot come back to ask for more because the answer will be “no.” (Before offering, youngest brother and I did assess our own abilities, and both of us actually do have very positive cash flow and healthy savings, and we have no uneasiness about our own extremely-low-interest obligations or other well-being.)

I recognize that in making this decision I am probably being pulled by the feelings of needing to be a “good sister” first. City brother has invented a story that he had such a tough childhood, was mistreated by family, etc. and has told me many times I “have a strong sense of justice, but no compassion,” so I know to some extent I am reacting to the hurt it causes to hear that from him. And if he is honest for a minute, he would freely admit that I have definitely gone out of my way for him emotionally and time-wise on many, many occasions.

But I guarantee you that youngest brother and I are sticking to our bottom lines! So, the next time City brother comes around with a request for even a little more money (which, honestly, we are expecting will happen), we are following the advice of Tightwad, catchingup, and DoingHomework and telling him “no”! Each of you are probably right that it is time for him to learn to fend for himself, but I’m not ready to tell him that today because he has literally just arrived in City, after a 5000 mile drive, to seek his dream career. However, certainly after this second loan, I will not hesitate.

+1. There is more than enough information here that the recent past is a bunch of empty promises intended to convince his siblings that he has turned over a new leaf and deserves more gifts (it's only a loan if it's ever paid back) .



Good luck. Knowing that you are being manipulated is the first step along the path of resisting that manipulation.

Do come back when (not if) he asks for more and tell us what happens!

Oh yes...it's update time, chica!
I forgot all about this thread.

So, y'all can feel free to say, "I told you so" . . .

Last you heard from me, October 2012, youngest brother and I had, together, already loaned City Brother $500 and then agreed to another $1,000. Soon after that, he paid back $15 (claimed that showed he was "turning a profit"), but just six days later, more loan money was "needed." Fast forward.

Since then, we made another four loans giving a grand balance of approximately $3,000. Three of these were for very small amounts, requested and made at the very last second when City Brother was under the gun to pay other people/services (hello, manipulation) and with pressure from parents to bail him out. The last was another $1,000 loan, mid-January 2013, made under express written terms whereby City Brother agreed to a detailed plan that we thought would best/most quickly lead him to a positive cash flow. Terms were clear as day, and City Brother accepted: " I agree with everyone and think the plan is SOLID. I DO want to swiftly accept the contract 'as is.' . . . Thanks so much for all the help. I think you have all went above and beyond expectations in your generosity! . . . I do want to make clear that I DO want your help, and I DO think your proposal is MORE than fair."

After that money was deposited in his account the next day, we received no thank-you or even acknowledgment that he had received the funds. Indeed, no word from him again for another week, when he was trying to convince me to provide another $500 for car issues. He immediately ignored all contractual terms and even orally admitted that he never had any intention of abiding when he wrote his acceptance but was just "desperate" for the money ("and if you don't like it, you can f*** yourself"). We haven't sent another dime since, and things have soured pretty badly. He doesn't want to talk to us too much because the loans make it "too awkward." We also learned that over the first half of 2012, dad had loaned City Brother a ridiculously large amount of money without any firm commitment of repayment (despite dad being in NO position to loan anyone any amount of money, and had I known, definitely would have changed my decision to start loaning in the first place). Despite that generosity from dad, City Brother became extremely nasty to him in February (when dad asked him why not following the loan terms), so that connection is at least temporarily severed, too. Only mom is really in touch with City Brother -- she probably will always feel bad for him and find excuses to justify his treatment of others. So, yeah, we read on facebook how he's "livin' the dream," etc. and just have to accept that he is who he is, but we are done giving financial support. Now the question is when/how we are going to start pushing for repayment since the reality is he's still in a line of work without any job security, barely cutting it, and the season ends in another month or two.

I'm sorry raindrop, that's really sad. It really sounds like your brother is experiencing some kind of addiction, whether it's drinking, drugs, gambling, etc. I'm a mental health social worker and drug rehab counselor, and that story is very familiar. I suppose it's possible that he's just an extremely reckless spender, but with the dollar amounts you listed, I doubt it.

I personally would forget about being repaid and just set a firm boundary going forward. Every loan is enabling his bad behavior.

I agree with ssarah..the loan is not going to be repaid, so no sense even thinking about it anymore. I wish you had known about your dad's loan too, because that would have saved you and your other brother from throwing 3k down the drain.

City Brother will come around again when he's ready for more money, and then he will not talk to you when you say no. It will be an ongoing cycle with him, so you just have to get used to hearing it. At least you can see him on FB and check in on him periodically to make sure he's ok.

Sorry about the situation; I know how it feels, and it's terrible.

I applaud you for coming back to update us -- no "I told you so's" here, it's never black and white when it's family.

I would agree that, at this point, you need to forget about ever being paid back and let that expectation go. You have done more than enough and it's City Brother who has soured this relationship, not you. Most important now is to have a plan in place for the next time he asks for money -- it will be an emergency, I'm sure. What will prevent you from giving in this time? You might need to cut off contact for awhile -- remove yourself from the situation so you don't weaken. He will never figure out how to be an adult if everyone coddles him and rescues him...so ultimately you'll be doing him a favor, even though it's one he may resent you for.

I wish you luck with this!

Okay...I told you so.


Shocker!


That's a given.


And this is where I would have taken my money out of his a$$.

Funny that city brother thinks the loans are making things too awkward. To me, the awkward point would be when he told you to go f*** yourself.

I'm sorry things turned out the way they did. I agree with Cely that you may want to decide upon a game plan so you'll be ready when he comes back to you asking for more money.

Wouldn't the game plan be to tell him to go f*** himself? Seems fair.

I rescued my brother last year, by borrowing from a family member to catch up on his car payments.

Originally it was mhy brother and I who was going to borrow the cash.

But I instead to my brother nah you don't have to make payments with me, I'll assume the responsibility on my own. (My brother was paying alot of bills since my brother was laid off and my stepmom at the same time).

So here I am straddled with a 1600 loan I am making payments on and my brother is still unemployed and I think he's behind on his car payments again.

I no longer help this brother monetarily.

I have been employed since the day I graduated college. They were not always the best jobs (sometimes more than one at a time). Initially I lived at home and paid rent - my mom needed the money. When the commute became impossible I moved closer to the city. The apartment wasn't the best but I managed. I think the struggle teaches discipline, independence and focus. Those experiences made me appreciate where I am today. And it made me intolerant for people like your brother. It is pity but your family's enabling denied your brother the opportunity to learn to be independent!

Like it or not there are shelfish people in this world- they will hurt other people and convince themselves they have done nothing wrong (its ll about me me me). Your brother is one of hose people. God bless you and your other brother for the help you provided. Now recognize he needs a different kind of help.

Ps since you and your brother are such softies...I was wondering if you could help a fellow out? I promise to pay you back just as soon as .....(pigs fly). Best to laugh at ourselves- lesson learned!

Gotta wonder too - drugs?

No no drugs, he's still stuck on spoiled.

Good news is this is a cheap final lesson.

He has asked since after the bail out.

I just say no.

Sorry to hear how things turned out with your brother...how disappointing. But sometimes the lessons we learn from the disappointment are invaluable

I'm sorry to hear the update, that he had not paid you back and was borrowing additional money from your father and from you and your younger brother at the same time. Experience can be a harsh mistress.
All I can say, is try to have you, and also your parents on the same line, about no longer, no matter was the emergency or whatever is going on, to financial bail out brother. If they cave during an 'emergency' all he will learn is how to escalate to get what he wants (the exact wrong message!)

My parents were constantly bailing out my older brother, to the point my parents are elderly, on limited incomes and completely supporting a 40 something man-child.

Unless your parents cut the money ties RIGHT NOW, they are by default signing an implicit promise to take care of a grown adult perfectly capable of supporting himself, for the rest of their natural lives. It is so important to do this while he can still learn, otherwise the patterns will be set (it already sounds like the pattern is being set).