My friend won't pay me back after I loaned her $2,500. How do I ask for repayment without ruining our friendship?

Dear For Love & Money, I have a good friend who was going through a financial hardship, and she asked me for a loan.

She assured me she would pay me back quickly.

I’m young and don’t have a lot of savings, so giving her $2,500 was most of my buffer.

It’s been months, and every time I bring it up, she puts me off or changes the subject.

I don’t want to lose my friendship!

Sincerely, Not a Loan Shark For Love & Money answers your relationship and money questions.

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Dear Not a Loan Shark, I’m sure you’ve learned your lesson, so I won’t beat you over the head with it, but for the rest of my readers, I feel like I should put the moral of this story into words: Loaning money to our friends isn’t always a good idea.

If your friend is in dire need of financial support and you can afford to help them, give them the money as a gift.

I know this advice may seem harsh, but my reason for giving it is summed up in your predicament: Healthy relationships have clear boundaries.

I learned this lesson from my own hard-won experience with a friend.

She and I shared one of those incredibly close, doing-life-together friendships where we hung out and took our children places together, constantly.

I began covering her dinners, her and her kids’ tickets to events, and reimbursing her for more than a tank of gas any time she drove us anywhere, because that’s what I always did with friends.

But, in my other friendships, this generosity was always reciprocal, and our tabs always roughly balanced out in the end.

Over time, however, I began to notice that with this friend, the giving was only going one direction, and a steady wall of resentment began to grow between us.

Even back then, I recognized that I couldn’t be angry at someone for allowing me to pay for things when I offered.

And because I never talked to her about it, I can only guess her motives for never getting me back, so I can’t dismiss her as a bad person either.

We never had a showdown over the topic, but we grew apart over an accumulation of personality differences, including money, and I’m no longer friends with this woman who used to be incredibly dear to me.

As unfair as it was, I found I struggled to respect someone who didn’t understand the unspoken social contract that the rest of my friends and I understood intuitively.

You know what would have saved me a lot of time, grief, and possibly our friendship?

Boundaries — both internal ones, like thinking, I paid for the zoo last time.

She can either get it this time, or we can both pay for our own going forward, and clearly communicating external ones, like saying, “Hey, since you’re driving, I’m going to pay for lunch,” rather than throwing money at her again and again, hoping she would follow suit.

Here’s my advice: No matter how tight your friend’s predicament is, you cannot give her money with the expectation that she will pay you back.

Setting this boundary might feel gross and unkind, but in reality, you’re protecting something important to you: your relationship with this person.

Boundaries are a little like fences; depending on your perspective, they can be unwelcoming and controlling, but they also serve as protective barriers.

If you value what you keep behind those barriers, why wouldn’t you keep it safe behind a fence?

That said, I recognize that it’s too late for this lecture.

Moving forward, in my opinion, you have two choices: One, prioritize saving the friendship, and call the loan a gift.

Or two, risk the friendship, and get your money back.

Before you make this decision, however, I would encourage you to evaluate your friendship.

On the one hand, perhaps she’s still the friend you love and trust, but she changes the subject because she still doesn’t have the money, and she’s embarrassed and stressed.

On the other hand, your friend could have entitlement issues, with no intention of paying you back, and she changes the subject every time in hopes that you’ll eventually drop the issue.

After reading both of those descriptions, which one feels more true?

If you decide to prioritize your friendship, reframing your perspective of the money as a “gift” rather than a “loan,” and accepting that the money is gone, may be your best bet for salvaging your relationship.

There’s likely a piece of you that feels betrayed by your friend, and justifiably so; $2,500 is no small sum.

However, if you can tap into the sympathy you felt for your friend when you first agreed to lend her the money, perhaps you can accept that her struggles are ongoing, and by giving her $2,500, you were an amazing friend who helped her when she needed it most.

I must warn you that this may not save your friendship.

Despite your best efforts to positively reframe your loan into an act of altruism, you might have lost trust or respect for her anyway.

Or, your friendship might implode for a completely unrelated reason, and you’ll just be left knowing you gave $2,500 to someone you no longer wave to on the street.

I hope this isn’t the case for you, but it’s important to consider before you proceed.

You mentioned that you’re young and that $2,500 was your emergency fund.

Not getting the money back may have put you in your own financial jam.

If this is the case, and you want accountability and repayment, it’s time for option two: Put your friendship on the line and get real with your friend.

Set up a coffee date and make it clear from the moment she sits down that you’re there to discuss one thing: the loan.

Be direct, remind her that it was a loan, not a gift, explain the situation she’s put you in, and ask her to come up with a plan to pay you back.

You can’t force her to open her wallet, but you can relentlessly redirect her if she tries to change the subject.

You can do all of this as gently as possible, in an effort to preserve the friendship, but in the end, like you, your friend will make her own choices.

No matter what, this conversation will likely be awkward and unpleasant.

It might end your relationship — either in the bang of a fight or the whimper of things between you becoming unbearably weird.

That doesn’t mean it isn’t the right thing.

Rooting for you, For Love & Money An earlier version of this article was originally published in September 2022.

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