May 20, 2025 at 11:15 pm

Hard-Working Guy Has Accumulated Wealth Thanks To Clever Business Deals, And Now His Family Want Him To Use It To Bail Out His Sister

by Kyra Piperides

A pile of US Dollars and physical bitcoin

Reddit/Pexels

Family is everything, right?

That’s what many people believe – and to everyone’s benefit when that family consists of good people who take responsibility for their own lives and needs.

But unfortunately those words are oft-repeated by a lesser kind of person too: the kind of person who things that because someone is their relative, they are automatically entitled to their time, their love, their money.

And when you’re confronted by that kind of person, those words mean only one thing: guilt-tripping.

That’s what the man in this story found out to his detriment, when he refused to financially support his sister.

His decision to not hand over the cash, ultimately showed him the true colors of not only his sister, but his parents too.

Read on to find out more about this family drama.

AITA for not helping my sister financially even though I could afford to?

I am a 32-year-old man, and I have done pretty well financially over the past few years thanks to a business I started that finally took off.

I recently bought a house and I live comfortably.

I am not rich, but I am in a good spot

My younger sister is 29, and has had a rougher time.

She works part time, and lives paycheck to paycheck.

Let’s see how their financial situations led to tensions between these siblings.

She recently asked me if I could help cover a few months of her rent so that she could catch up on bills.

The thing is, this is not the first time I have helped her, and every time I do it ends up becoming a pattern.

I told her gently that I could not keep bailing her out and that I wanted her to find something more stable.

Read on to find out how his sister reacted to his words.

She got upset and told me that I was being selfish, and that family should help each other no matter what.

Now my parents are involved.

They think I am being cold and that I owe her some support since I have more than enough.

I am trying to set boundaries, and trying not to feel guilty for saying no.

AITA?

Financial decisions are a very personal thing, and he has absolutely no obligation to help anyone out.

In fact, the people who are telling him what to do with his money are entirely in the wrong.

How is she going to learn financial independence if he keeps bailing her out?

Let’s see what the Reddit community thought about this.

This Redditor agreed that the sister needed to learn to support herself.

Screenshot 2025 05 08 at 10.40.51 Hard Working Guy Has Accumulated Wealth Thanks To Clever Business Deals, And Now His Family Want Him To Use It To Bail Out His Sister

While this person pointed out the guilt-tripping that was occurring.

Screenshot 2025 05 08 at 10.39.55 Hard Working Guy Has Accumulated Wealth Thanks To Clever Business Deals, And Now His Family Want Him To Use It To Bail Out His Sister

And others explained that family does not equal obligation.

Screenshot 2025 05 08 at 10.41.48 Hard Working Guy Has Accumulated Wealth Thanks To Clever Business Deals, And Now His Family Want Him To Use It To Bail Out His Sister

If his sister needs more money, she needs to get a better (or at least full-time) job.

We all fall on hard times occasionally, and it’s clear that he’s helped her out before.

At some point, she needs to learn to help herself.

If you thought that was an interesting story, check out what happened when a family gave their in-laws a free place to stay in exchange for babysitting, but things changed when they don’t hold up their end of the bargain.