What do you think of it bothering me always paying for dinner for this reason?

[Anonymous]

I’ve got plenty of money. I can afford to pay for it, but we have dinner out with my mother and grandfather / occasionally a sibling or something almost every week. I hope he lives a very long time and he runs out of money, however, I don’t think he realizes that by me paying for it I am by proxy, giving my money to my aunts who are not nice people. The Will states that it is split up between the three sisters. Hopefully he will actually need money one day and if he does, we will take care of that. But really, it makes more sense for him to spend the money he has, because every penny is not spending means they get more. So essentially of every dinner tab I pick up 2/3 of that is going to people who I don’t want to give it to. This is going to add up to many thousands of dollars over the years. I just don’t think it’s right that God forbid something happens in the span of that time that I’m giving the money. That’s what it feels like. This will be a very awkward thing to mention though. I think if he offers to pay for a bill at some point, I’ll just let him but he hasn’t been doing it very much really..

[Oliverlogan263]

Damn bro, that is really annoying that you're always the one paying for dinner like that. I get why it bothers you so much. It's not even just that you're spending your own money, it's that with how the will is set up, you're basically funding your aunts indirectly. And if they're not cool people, that sucks even more.

I wouldn't feel right about that situation either if I was in your shoes. At the same time, bringing it up to your grandpa could definitely cause some drama. Old people can be really stubborn about money stuff.

Here's what I'd do - next time you're all going out, just casually be like "hey grandpa, mind grabbing this one? I've had the last few." Try to play it off light and like it's no big deal. Then maybe suggest taking turns paying from now on so it's fair.

If he still doesn't get the hint, you could tell him you want to treat him more but feel bad the money is kind of supporting aunts he may not want to. Frame it like you just wanna make sure he's comfortable with how it's set up, not like you're demanding anything.

Hopefully he comes around. But keep treating him nice regardless - you never know what the future holds. Good luck man, hope you can work it out!

[Staximus]

If your shitty aunts aren't there at the dinner then you're being a dumb ass.