I Refuse to Keep Paying the Price for My Best Friend’s Choices

Friendship has its ups and downs, but when finances are involved things can get tricky. We tend to work on budgets and try to help where we can, but it isn’t always that simple. If someone needs help too often, it can feel like we’re being manipulated and used.

One of our readers, Jason, reached out to us.

Dear Bright Side,

I’ve always worked hard and did whatever it took to make it through the month. Because of that, I managed to build a nice life for myself and my fiancé. But my best friend, Dane, never kept a steady job. And he’d borrow money, promising to repay, but he never did.

We’ve been friends since high school, but when I started working in my teen years, build a career for myself and paid off all my debts. He decided to enjoy the ride. He spent his life having fun and living off borrowed funds, which mostly came from me, and he never paid back a cent.

There hasn’t been a time when he kept a steady job or lasted at a company for more than a couple of months. So he kind of just bounces between gigs and tries to find ways to get rich quick. But somehow he always ends up needing more.

Over the years, I’ve heard every promise and excuse in the book. “I just need a bit until Friday,” or “I’m sorry, but I had to buy food, can I pay you next week?” But we both knew it was never going to happen. Yet, I continued to support his habits with the hope that someday it would work out.

He was my best friend, after all, and I wanted him to have all the best, even if it cost me a bit here and there. His family situation wasn’t the best, and he often struggled with things he didn’t want to talk about, so I told myself it was worth it and kept on giving.

Then one day, a few weeks ago, he called me. He was absolutely sobbing when he explained that he just found out his girlfriend was pregnant, and he needed a bit of money to take her to the doctor. “Please, this is the last time, I promise,” he said.

That day, something in me snapped, and I said. “Sorry, but I can’t.” He kept pleading, saying he had no other way, but I didn’t listen. I kept telling myself that he was just trying to guilt-trip me into getting what he wanted.

A few weeks later, I tried to call him and was surprised to find that he had blocked me. A couple of days after that, his girlfriend contacted me on social media. She told me to leave him alone because I had already cost them everything.

I was shocked and confused, so I asked her what she meant. She told me that he used their rent money to cover her doctor’s visit. It was their first ultrasound, and he didn’t want to miss it. But shortly after that, they got evicted, and they had nowhere else to go.

Her words broke me. If I had known the situation was that bad, I would’ve made a plan to help him out. But instead of giving him a chance I just assumed the worst and because of that he’s homeless. I tried reaching out a few times, but he’s refusing to take my calls.

So Bright Side, what can I do? Is there a way for me to fix this situation and help my friend, or am I too late?

Regards,
Jason L.

Thank you for reaching out to us. We understand how challenging a situation like this can be and have put together a few tips that might help you.

Don’t confuse boundaries with assumptions.

It is important to say no when your limits are being pushed. But remember that your answer needs to come from a place of understanding. Because your friend has a reputation of doing such things, doesn’t mean that it can’t be serious. You need to ask questions and make sure that the decision you made comes from a good place. And don’t just set boundaries out of the blue like that. Things like that need to be discussed and the reasons and stipulations need to be made clear.

Long-term enabling doesn’t prepare people for a true crisis.

Remember that you have been enabling Dane his entire life. So who do you think he will turn to when things get rough? You have also shown him that he doesn’t need to give explanations for what he needs because you’ll come through no matter what. That’s why you didn’t see how serious the situation was. You assumed instead of questioning, as you have always done.

Make your apology clear and expect nothing in return.

You can’t go back and change the past but you can work toward fixing what was broken. You can approach your friend with humility, not guilt and apologize for jumping to conclusions. If he refuses to see you write your apology out and send it to his girlfriend. Explain what happened that day and make sure he knows you don’t expect forgiveness or a reply. What you’re trying to do is rebuild the trust you had and that doesn’t happen over night.

Rebuilding trust isn’t easy, especially in a situation like this one. But it is possible. Jason deserves a chance to explain just as Dane has the right to be heard.