I've loaned my sister thousands over the years. Now that she has a high-paying job, how do I get her to pay me back?

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• For Love & Money is a column from Business Insider answering your relationship and money questions.
• This week, a reader wants her sister to pay her back a decade's worth of loans.
• Our columnist says she should be direct about what she wants, but open to creative repayment.
• Got a question for our columnist? Write to For Love & Money using this Google form.

Dear For Love & Money,

Over the years, I've loaned my sister money whenever she needed it. I helped her purchase her first car, put her on my phone plan and often covered the monthly bill alone, made sure she could attend the annual trip our cousins put together, and more.

I've done it because I'm her older sister, and she has usually agreed to pay me back eventually. I never hassled her about it, as she was young, struggling, and not in a place to repay me yet.

Recently, my sister landed a high-paying job, earning more than the rest of our family combined. While I'm married with a kid, she's unattached and has no real responsibilities beyond herself. I'm proud of her and don't resent her success.

I've realized, though, that if she paid back even some of the money she owes me, it would really help my family. I tallied how much she's borrowed over the years, and excluding all the things we never explicitly called loans, the total comes to $5,000.

Since she started making more money, I've mentioned her paying back some of what she's borrowed from me. Her response is always, "Yeah, yeah. I get it. You've helped me a lot over the years," but she seems to have completely forgotten that these were always supposed to be loans, not gifts.

To her credit, since she's been earning more, she pays her share of the phone bill and covers her portion of the cousin's trip, but that's not the same as paying her debts. How do I ask her to pay me $5,000 for loans going back 10 years?

Sincerely,

Generous to a Fault

Dear Generous,

I can think of few trickier interpersonal conflicts to navigate than disagreements over whether a financial boost from a friend or family member was a gift or a loan. We like to believe that if we spell these things out early on, we avoid arguments or awkwardness later.

However, as cases like yours demonstrate, if enough small amounts of money have been exchanged over a long period, and there's familial comfort involved, everyone will still often (and conveniently) remember things differently. This isn't to say your sister will disagree with you if you ask her for repayment outright, but her dismissive response to your nudging suggests she might.

Maybe your sister is doing this intentionally, or maybe it's an honest misunderstanding, or perhaps it's simply a difference in worldview. She may feel like this is how family takes care of each other, and there's no way you really ever planned on making her repay you. I'm positive I will receive at least a few messages from readers offended by my suggestion that this could be a reasonable thing for your sister to feel, but I will also receive several upset that you ever expected your little sister to repay you in the first place. The truth is, it's simply a difference in value systems, and a valid one at that.

Whatever your sister's reasons for failing to pay you back, they have little bearing on what you want to do about it. Instead, you must base your decision on your desired outcomes. Obviously, you want your money back. Who wouldn't appreciate a $5,000 cash injection?

And since you both agreed these were loans back when you gave them to her, she owes you. However, if she disagrees with you, you must ask yourself what you're willing to risk if you keep pushing the issue, and what you risk by dropping it. Are you OK with hurting your relationship with your sister if it gets you the money you're owed? But also, if you choose to forget the debt and move forward, are you OK remaining quiet in a relationship with someone who has treated you this way?

If you decide to press the issue, you must ensure your sister is actually opposed to paying you back — no casual references to old loans or passive-aggressive comments about what she ought to do with her new spending power. Tell your sister outright that you're calling in her loans.

I understand being this direct in a relationship is scary. Shining a light on a decade's worth of awkward exchanges over unpaid phone bills and generously covered vacation rentals will probably reveal many other things best left in the past. Being this clear about your expectations will also require you to show your financial hand to your younger sibling. A sibling you have spent years taking care of will now see how much $5,000 means to you — more, it seems, than that amount of money means to her at this point. This may feel humbling to you as a big sister, but you won't get far without honesty.

You should also consider being creative about how she repays you. Not even people we consider wealthy necessarily have $5,000 lying around to hand over at a moment's notice. You might suggest your sister pay you in installments, cover the entire phone bill for a while, or pay your share of the cousins' trip until she's repaid her debt.

As long as you're both clear on the plan and keep track of where she's at in her repayment, this could be an excellent way for her to ease your life in the same way you eased hers over the years without hitting her wallet too hard.

If you're reading this letter thinking, "Yikes. I don't want to have this conversation. I'd rather forget the past and avoid a huge sister showdown," that's fair too. Just remember that the choice is yours to make. Whatever you choose to do, the good news is that your little sister is no longer one of your financial responsibilities, and that alone is going to save you money.

Rooting for you,

For Love & Money

Looking for advice on how your savings, debt, or another financial challenge is affecting your relationships? Write to For Love & Money using this Google form.