March 15, 2026 at 10:23 am

Generous Friend Closed His Wallet After Hundreds Went Unpaid, But The Indebted Buddy Tried Guilt And Insults To Squeeze Out Another $100

by Benjamin Cottrell

two men arguing

Pexels/Reddit

Some friendships start to feel less like bonds and more like bank accounts with no withdrawal limits.

So when one lender realized his so-called “friend” had stacked up hundreds in unpaid loans and was asking for “just one more” $100 payout, he finally refused to keep financing the cycle.

His firm financial boundary soon sent his entitled buddy into a guilt-tripping spiral.

Keep reading for the full story.

AITA for telling my friend I wouldn’t lend him $100 for transportation to work

Basically my friend is broke, like 0 money, but just got this new job.

The problem is he needs transportation and is broke, so no car. But buses exist.

So when his friend asked him for money, it put him in a tough spot.

He hit me up asking for a $100 loan to pay for bus fare, and in exchange he’d pay me back $200 when he gets paid.

Now I know what you might be thinking: it’s only $100, and if you guys are friends then you shouldn’t have a problem helping because friends help each other.

I think the same.

But this friend has quite the troubling history.

However, this is someone that has hundreds worth of loans from me and hasn’t paid me back.

Now, so far the reason for this has been no job, so I let it slide.

But honestly, I’m ticked having to somehow give back-to-back loans from me and seeing no effort to even pay a little back.

So he was firm with his friend, and his friend didn’t take it well at all.

That’s what I said: No, I won’t loan you any money because I’ve given you multiple loans and you never pay them back.

So he responds, it’s not that I won’t, I can’t, and you’re being a jerk over just a few hundred in loans.

And I didn’t have opportunities like you.

$100 isn’t even that much. You’re rich.

A small part of him feels bad for his friend, but another part feels indignant that his friend feels so comfortable taking advantage of him.

So now I don’t know what to think because yes, it’s true he hasn’t been able to pay me back because no job.

But secondly, I have very little faith or trust because it’s multiple back-to-back loans and no attempt to pay back, like through trying side hustles or gig work.

Obviously not everyone can do those or have that available. But it’s the lack of effort to even attempt that.

So then, am I the AITA for not giving the loan?

Friends and finances just don’t mix well.

What did Reddit think?

Sooner or later, his friend needs to accept the consequences of his actions.

Screenshot 2026 02 25 at 12.33.03 PM Generous Friend Closed His Wallet After Hundreds Went Unpaid, But The Indebted Buddy Tried Guilt And Insults To Squeeze Out Another $100

When you let someone take advantage of you once, they’re more likely to do it again.

Screenshot 2026 02 25 at 12.33.36 PM Generous Friend Closed His Wallet After Hundreds Went Unpaid, But The Indebted Buddy Tried Guilt And Insults To Squeeze Out Another $100

This person might need to come to grips with the fact they may never see this money again.

Screenshot 2026 02 25 at 12.34.24 PM Generous Friend Closed His Wallet After Hundreds Went Unpaid, But The Indebted Buddy Tried Guilt And Insults To Squeeze Out Another $100

Real friends don’t treat each other this way.

Screenshot 2026 02 25 at 12.35.02 PM Generous Friend Closed His Wallet After Hundreds Went Unpaid, But The Indebted Buddy Tried Guilt And Insults To Squeeze Out Another $100

If finally standing up for himself makes him the bad guy, then so be it.

No one’s got time for broke-boy logic like this.

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.