How many times do you have to bail someone out before enough feels like enough?

What’s helping, and what’s enabling?

It can be a difficult line to parse out, as evidenced in this story:

He can afford to help his sister, but he doesn’t think that’s the right thing to do. Yet, the guilt is real, and he’s not sure exactly what is right anymore.

Let’s read the whole story.

AITA for not lending my sister money even though I have a high paying job now?

I (28M) recently started a new job in tech that pays really well.

Honestly, it’s the most money I’ve ever made in my life, and it’s completely changed how I live.

I grew up in a single parent household, and my older sister (32F) was a huge part of my life when we were kids.

Our mum worked two jobs, so my sister kind of took on a parental role when she was still just a teenager. She cooked for me, helped me with homework, made sure I got to school on time.

I’ve always been thankful for that.

But she hasn’t gone down a great path since.

The issue is, her adult life has been pretty messy.

She’s never been great with money. She’s bounced from job to job, tried a bunch of different “business ideas” that didn’t go anywhere, and constantly asks people to loan her money or invest in things.

She doesn’t have any savings and has borrowed from our cousins, our mum, and even old friends.

A lot of those relationships are strained now.

Now it’s time to strain yet another, it seems.

A couple of weeks ago, she called me and said she was being evicted. She asked if I could give her $5,000 to help her stay in her place. She said she’d pay me back as soon as things “picked up.”

That’s something she’s said before.

I told her that I couldn’t give her that kind of money right now.

I’ve been saving up for a house deposit and trying to be smart with my finances.

She got really upset and told me that I wouldn’t even be where I am if it weren’t for her raising me. She said she gave up her childhood for me and that I’m basically abandoning her now that I’ve “made it.”

He feels very conflicted.

I tried to explain that I appreciate everything she did when we were kids, but I also can’t keep giving out money when I know there’s a good chance I’ll never see it again.

She hung up on me.

Now our mum is texting me saying my sister is sleeping on her couch and that she’s in a really tough spot. She says I’m turning my back on the one person who was always there for me.

The guilt is real.

I feel guilty. I really do.

But I also feel like my sister brings these situations on herself and expects other people to fix them.

I’m not sure what the right thing to do is anymore.

AITA for not helping her this time?

When it is help and when is it enabling?

Here’s what the comments on Reddit made of this:

This person can relate to the sister.

A lot of finger pointing going on.

But your choices aren’t all or nothing…

Others preached tough love.

Here’s hoping sister can find her way out of the spiral.

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.