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Wedding Woes

Talk to Jay and tell him to figure out how to pay taxes.

Dear Prudence,

I have a younger brother “Jay,” who, although he’s in his mid-30s, is a man-child who refuses to learn how to handle life. I could go on and on, but there is one issue for the sake this letter. For background, a few years ago, Jay received a monetary settlement after he was injured in an accident. With that money, he bought a small house outright. Recently, my parents told me that eventually when they pass, I will have to be responsible for paying the taxes on Jay’s house. Not with my money—they will leave some money in their will, but I will have to make sure the taxes get paid because Jay will never remember to do it. My parents, especially my mom, enable Jay so much. They don’t give him a lot of money, because they don’t have a lot, but they do things for him that as a grown-ass adult, he should figure out how to do on his own. I told them on no uncertain terms that I was not managing his life for him, and they got really upset and said they couldn’t believe I’d let him lose the house and let him be homeless. I’m not sure what to do. I don’t want to placate them by just saying yes because I’m not going to do it, and they need to start teaching my brother NOW that he needs to be responsible for his life! How do I have this conversation with them?

—Not My Brother’s Keeper

Re: Talk to Jay and tell him to figure out how to pay taxes.

  • Tell them that they can give the tax money in a lump sum to this brother, but that after that it is in his hands and his hands alone.  Other sibling should not be responsible for minding him afterwards, and the guilt of "will you let him be homeless" is not on the siblings but the grown man who can't remember to set up auto pay.

  • LW's parents are being ridiculous and I think LW should die on this hill.  But I also think a courtesy head's up to Jay is required here.  

    I'm very confused as to why they are spending all this energy on telling LW how to continue to care for their brother vs. spending it teaching him adulting basics.  I really try to understand people like this, but it's super hard for me to get past my judgement of these situations.  
  • LW is expected to do this for the rest of their life? And depending where they live, how do the parents even know how much to leave? Taxes are going way up. I couldn’t project what they’ll be 10 years from now.

  • Is brother physically or mentally disabled after this accident to the point where he needs extra assistance? If not then he needs to be told to grow up and get it together. 


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  • I can't imagine this is the only adult issue that Jay needs to figure out, stat.

    Does the house not have insurance?  What about that?  What happens if the insurance company yanks his policy for no reason or goes out of business?  I have had both of those things happen to me.  Let me tell ya, getting a new policy in only 30 days is way more complex then paying the property taxes when they're due.

    What about utility bills?  Or does he just wait until it's shut off to be his reminder to pay, lol.

    The parents are still alive.  Great.  Now is the time for them to finally train their son to get his shit together and handle the basics in his life.  Have him put reminders on his phone/calendar.  Discipline himself to take care of bills/important matters as soon as he gets it in the mail.  
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  • Either they can teach Jay how to pay taxes, or they can set up a fund with an attorney/ a trust at a bank to have them paid out from the estate. The second is going to cost a lot more for something Jay can easily learn how to do (assuming he has the ability to do so). 
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