April 2, 2025 at 6:48 pm

His Parents Enabled His Older Brother’s Mistakes Over And Over, So The Constantly Overshadowed Sibling Finally Had Enough And Walked Away

by Benjamin Cottrell

frustrated man covering his face with this hand

Shutterstock/Reddit

There’s a fine line between helping and enabling, and some parents don’t know when they’ve crossed it.

One man spent years watching his brother make mistake after mistake, only to be bailed out time and time again. But when his parents chose to sacrifice their own future to save their screw-up son, he decided it was time to walk away for good.

You’ll want to read on for this one.

AITA for Telling My Parents They Need to Stop Enabling My Brother or Im Cutting Them Off?

I (30M) have an older brother, Ryan (34M), who has always been the family screw-up.

He’s been in and out of jobs, relationships, and even short stints in jail for stupid stuff (DUIs, unpaid fines, etc.).

His parents always react the same way.

Every time he messes up, my parents bail him out —paying his rent, covering legal fees, even buying him a car after he crashed his last one.

Meanwhile, I worked my butt off, put myself through college, and built a stable life.

My parents have never given me a dime.

I never asked, but it stings when I see them constantly throwing money at Ryan while I get told, “You’re doing fine on your own.”

So he decided he was done watching Ryan get everything.

The breaking point came last week when my mom called, crying, saying Ryan got evicted again and needed a place to stay.

I told her no.

She said she and Dad were planning to cash out part of their retirement fund to get him a new apartment.

That’s when I lost it.

He snapped and started telling his parents off.

I told her they needed to stop enabling him or they’d end up broke and alone because I was done watching them ruin their own lives for someone who never learns.

I said if they keep bailing him out, I’ll go low contact because I can’t keep watching this cycle.

His parents try to make him feel like a bad person because of it.

Now, my parents think I’m heartless.

My dad said I’m turning my back on family, and my mom won’t even talk to me.

Meanwhile, Ryan has been texting me nonstop about how I’m a selfish jerk who thinks he’s better than everyone.

Now he feels stuck in an impossible choice.

I don’t want to abandon my parents, but I also refuse to stand by while they self-destruct for someone who doesn’t care.

So, AITA?

It’s hard to watch someone close to you throw good money at bad decisions.

Let’s see what Reddit has to say about this.

This commenter isn’t sure his parents are the type of people he needs in his life right now.

Screenshot 2025 03 19 at 2.07.32 PM His Parents Enabled His Older Brothers Mistakes Over And Over, So The Constantly Overshadowed Sibling Finally Had Enough And Walked Away

The parents have a solution right in front of them, so why aren’t they taking it?

Screenshot 2025 03 19 at 2.09.07 PM His Parents Enabled His Older Brothers Mistakes Over And Over, So The Constantly Overshadowed Sibling Finally Had Enough And Walked Away

If this user’s prediction is correct, things could get a lot worse.

Screenshot 2025 03 19 at 2.09.53 PM His Parents Enabled His Older Brothers Mistakes Over And Over, So The Constantly Overshadowed Sibling Finally Had Enough And Walked Away

He’s tried his best, but you can’t help someone who doesn’t want to be helped.

Screenshot 2025 03 19 at 2.11.04 PM His Parents Enabled His Older Brothers Mistakes Over And Over, So The Constantly Overshadowed Sibling Finally Had Enough And Walked Away

Families are supposed to lift each other up, but some people just never learn to stand on their own.

If you thought that was an interesting story, check this one out about a man who created a points system for his inheritance, and a family friend ends up getting almost all of it.