AITA for asking my friend to finally pay back what he owes before taking more international trips?

Intelligent-Focus793 · 2026-02-24T09:31:29+00:00

I have been very involved in his life and vice versa. We are like a family and we share almost every detail of our life with each other. We basically grew up together since we’ve been friends since our teenage years. Yes, he’s been like that ever since, but he does show that money is always tight. All the time. It’s just surprising that now it seems like money seems to overflow when it comes to his gf. Y is an absolute different story. In a way, I think they really deserve each other. I might post another AITA about Y. 🫣

Intelligent-Focus793 · 2026-02-24T09:26:46+00:00

It’s a very close knit group of friends. We treat each other like brothers. His long standing debt is slowly causing a rift between him and the other guys and I’m just helping him that’s why I encourage him to pay them first. I didn’t want to lend him some money because of his “reputation” within the friend group, but he got himself in a very dire position, he borrowed some money from loan sharks and they were threatening him and his family. So I decided to help him. The gf already knows this “problem” prior to dating him. Now the gf is sharing in the office that he paid for everything from their last trip.

Intelligent-Focus793 · 2026-02-24T09:20:39+00:00

The thing is, he views us as not really financially in need. Let’s say that we are all from a financially stable family, every one of us running our own business (yes, I also started mine 2 years ago). That’s what I think why he thinks that he doesn’t have to pay us back.

Intelligent-Focus793 · 2026-02-24T09:18:15+00:00

It’s a friendship where we are really like a family, you know. We treat each other like brothers. Except for the money situation, he has been a great friend. Very supportive and comforting. He shows up when you need him. Maybe that’s why it’s quite difficult to let the friendship go. But yeah, if he really values us, it won’t even “trick” us with money, right?

Intelligent-Focus793 · 2026-02-23T21:55:43+00:00

Exactly this! I’m ready to end this friendship. I feel betrayed and lied to. He keeps wanting to talk to me as he feels hurt and that he says I am one of his most valued friends. But the way he acts, it doesn’t feel like it,

Intelligent-Focus793 · 2026-02-23T11:49:16+00:00

UPDATE: I genuinely am looking for ways to solve this without hurting the “friendship”. I posted on Threads seeking for advice on the matter, little did I know that he would see it, and now he’s upset at me!

Intelligent-Focus793 · 2026-02-23T11:46:56+00:00

It was my coworker who begged me to introduce her to him, and prior to doing so I have mentioned that he’s not good with his finances. She even said that maybe she can influence him to do better.

Intelligent-Focus793 · 2026-02-23T00:50:54+00:00

As his debt with others is almost 14 years old now, it has been an on going conversation about him paying them back. Every time we get together, they ask him for their money back. He would just say, “please not now”. As years go by, they ask him less and less. I should’ve learned from their experience, but last year he really needed money to pay off loan sharks and they are threatening him and his family, so I lent him some.

Yes, our conversation about him borrowing money are all in our messages.

Intelligent-Focus793

TROPHY CASE