October 8, 2026 at 8:15 am

Man Asked His Father To Take His Jobless Sister Off The Estate, So More Money Could Go To Siblings Raising Children

by Benjamin Cottrell

man using a calculator

Pexels/Reddit

Estate planning is supposed to be about protecting a family, but sometimes it ends up exposing how each person thinks fairness works.

One man was co-executor of his father’s estate with his sister, and his father had been paying her roughly $2,500 a month during six months of unemployment.

The man, who has three children, and another brother, who has two, felt that gap mattered, since their sister was childless and planned to stay that way.

So he asked their dad to take her off as executor and shift the money toward the siblings with kids.

Read on — Reddit had a lot to say about this one.

AITA For trying to make sure that My Father’s estate is shared appropriately?

My (38M) sister (31F) has been unemployed for about 6 months.

Being the oldest of our 4 siblings, we are both assigned as executors of our father’s estate. Thankfully, Dad is still with us.

He describes more background on the family.

In the past 6 months while my sister (31) has been looking for a job, our father has been helping her with bills, to the tune of about $2500 a month.

For more background, this sibling does not have children and never plans to. I have three children, and another, younger sibling (27M) has two children.

Soon he begins to wonder whether the status quo is really working for the family.

I asked Dad, taking into account he has spent so much on my sister, and that she doesn’t have kids, shouldn’t she be removed as executor of the estate, and the money be weighted towards those with children?

So I ask, AITA in asking that my childless sister, who has already taken money from our father, should be removed from the will as an executor?

Sounds like this is going to be an uphill battle.

Reddit is sure to have some strong opinions on this one.

This commenter sees right through the façade.

Screenshot 2026 10 06 at 12.54.51 PM Man Asked His Father To Take His Jobless Sister Off The Estate, So More Money Could Go To Siblings Raising Children

The whole situation puts a bad taste in this reader’s mouth.

Screenshot 2026 10 06 at 12.54.21 PM Man Asked His Father To Take His Jobless Sister Off The Estate, So More Money Could Go To Siblings Raising Children

This redditor doesn’t like the implications this man is putting on child-free people.

Screenshot 2026 10 06 at 12.54.41 PM Man Asked His Father To Take His Jobless Sister Off The Estate, So More Money Could Go To Siblings Raising Children

If you enjoyed this story, check out this post about a mom who thinks her daughter should have planned a whole two-week vacation around her needs.

This reader brings up a similar point.

Screenshot 2026 10 06 at 12.54.51 PM Man Asked His Father To Take His Jobless Sister Off The Estate, So More Money Could Go To Siblings Raising Children

The timing alone makes this request super sketchy.

Shouldn’t this man want his struggling sister to receive the help she needs instead of preemptively trying to squeeze as much out of the estate for himself?

Their father is still alive and the money is still his, so it’s time to trust him with it.

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Benjamin Cottrell | Assistant Editor, Internet Culture

Benjamin Cottrell is an Assistant Editor and contributing writer at TwistedSifter, specializing in internet culture, viral social dynamics, and the moral complexities of online communities. He brings a highly analytical, editorial voice to his reporting on workplace conflicts, malicious compliance, and interpersonal drama, with a specific focus on nuanced stories that lack an obvious villain.

As a published author of rhetorical criticism, Benjamin leverages his academic background in human communication to dissect and elevate viral social media threads. Instead of simply summarizing events, he provides readers with balanced, deep-dive commentary into why the internet reacts the way it does. In addition to his cultural reporting, he is an experienced fine art photography essayist and video game reviewer.

When he isn’t analyzing the latest viral debates, Benjamin is usually chipping away at his extensive video game backlog, hunting down the best new restaurants, or out exploring the city with a camera in hand.

Connect with Benjamin on Instagram and read more of his essays on Substack.