Pay Dirt is Slate’s money advice column. Have a question? Send it to Kristin and Ilyce here. (It’s anonymous!)

Dear Pay Dirt,

I need advice on how to handle money with my friend group. There are four of us who hang regularly, two are a couple who recently bought a house (we’re all in our early 20s, for context). Because they have the house, they’re the default hosts, and because they host, they often end up paying for things like food and covering things like entry tickets for logistical convenience. Except then they turn around and say not to worry about it when I offer to pay them back for those things, which makes me uncomfortable. There are a few reasons for this, but the main one is the aforementioned house. They told me how much their mortgage is, and I know roughly how much the pair make. The (admittedly back of the napkin) math doesn’t totally math.

I don’t think they know how much I make, nor how lucky I’ve gotten with being able to live comfortably and save on that income. It’s on paper a bit less than their combined income, but I don’t have a mortgage! So, whenever we’re out I try to make sure I pay them back, and have to hold myself back from giving them extra to help with the mortgage. I’ve never broached the latter idea because I have no idea how they’ll take it. I can tell the way I handle money at our hangouts is starting to grate on them (I feel like a collections agent for myself occasionally), but I don’t know what else to do. It feels invasive to ask about their finances, but also from the outside looking in it feels like they’re needlessly throwing it away!

Is there a way for me to broach the conversation of them letting me pay for things? Do I start pulling the grandma trick of hiding cash in their stuff when I visit? I just want to make sure the people I care about are OK and not stretching themselves too thin for me.

—Let Me Help, Please

Dear Let Me Help,

No need to pull the grandma trick just yet. (Although, your grandma sounds great  — can I borrow her?) You mentioned that your friend seems annoyed with your money handlings, so a conversation is your best bet here. The key is to frame it around fairness and your own discomfort rather than their financial situation.

A simple way to start the conversation: “Can we talk about how we’re all splitting things? I don’t feel comfortable not paying my fair share. I’d be really happy if we could start splitting things more evenly. Is that possible?”

If they brush things off, you can make some suggestions, like rotating who picks up the tab at dinner or hosts the next hangout. Or, you could agree to bring the dessert or the side dishes. Or even help with cleanup.

It’s totally reasonable that you want to pay your fair share and it’s sweet that you’re looking out for your friends. But they’re also adults and, for all you know, they might have other sources of income you’re not aware of. They might have gotten a big windfall and enjoy spending it on their friends—who knows?

Either way, hiding money could turn a slightly uncomfortable situation into a really awkward one, so don’t be afraid to be direct and bring up the topic next time they seem annoyed by the quid pro quo.

Please keep questions short (<150 words), and don‘t submit the same question to multiple columns. We are unable to edit or remove questions after publication. Use pseudonyms to maintain anonymity. Your submission may be used in other Slate advice columns and may be edited for publication.

Dear Pay Dirt,

I have $140,000 of student loan debt for a bachelor’s in a science field. The debt is due to a combination of complete lack of parental support (both financially and in terms of decision-making support) and being in a relationship through college and after that was abusive, including significant financial abuse. The debt is pretty evenly split between federal and private loans. I have been making payments on the private ones, but the balance never really goes down (and I have refinanced to get an okay rate, about 5 percent). The federal loans have been ballooning with interest while on forbearance.

I have also developed an autoimmune condition that limits my ability to work but doesn’t qualify me as disabled—my field normally involves heavy outdoor labor that I am simply not capable of now. I am eligible for public service loan forgiveness, but I can’t afford the payments for that plan. I make $62,000 gross in a medium-cost-of-living city. I have looked actively for higher paying jobs but have found nothing better (my field has been severely devalued in recent years). Also, at this point, I truly cannot afford to lose the fantastic healthcare my current job provides.

Other than this debt, my finances are in great shape. I have no other debt apart from a 3 percent mortgage on a cheap house (rentals for a one-bedroom apartment here go for about double what my mortgage, insurance, and taxes cost me monthly). I also have a small amount on a credit card for some work on the house that I can pay off interest-free by the end of the year. I have no car loan, don’t travel, don’t get fancy coffee or eat out much, rarely buy new clothes, have no expensive hobbies, etc. I’m naturally frugal and expenses are already cut to the bone. I maintain the house alone which gets more expensive every day, but my abusive ex is on the mortgage and the title, although they finally stopped living here last year.

Is there any way out of this? I know that student debt is typically non-dischargeable through bankruptcy, but I have heard of things like adversary proceedings. I have thought of paying all my living expenses through credit so I can try to pay the loans (I’ll be forced into this at some point regardless of whether I want to do that or not, because I simply won’t have enough money).

—Other Than Win the Lottery

Dear Win the Lottery,

You’ve had a lot to deal with, and the fact that you’ve kept your financial life fairly stable through all of it is a testament to having solid money habits. There’s probably no magic fix here, otherwise we’d all be using it. The good news is, there are ways to move forward.

You’re right that, historically, student loans have typically been non-dischargeable in bankruptcy (or at least, really hard to get discharged), but the process has changed in the past few years. Yes, adversary proceedings do exist, and medical limitations might help you qualify. It’s a difficult but not impossible process, and you can schedule a consultation with a bankruptcy attorney to see if you might be a good candidate. Depending on your medical issues, you might also look into Total and Permanent Disability (TPD) discharge.

I Was Happy to Give My Best Friend a Plus-One to My Wedding. But I Might Have to Draw the Line at This Latest Addition to Their Family.

It might also be worth talking to a non-profit credit counselor who can look at your full situation and help you come up with a plan to pay off your debts over time. That’s a much safer route than putting your living expenses on credit, which will only get you further into a debt trap. Chances are, they’ll help you come up with some version of a debt snowball or debt avalanche where you prioritize paying off one debt while making minimum payments on the others. Right now, your priority might be paying off that credit card. Because even if you have until the end of the year until interest accrues, I’m guessing that interest rate is going to be through the roof if you don’t pay it off in time—it’s kind of what the credit card companies are banking on, and it could make your situation considerably worse.

Sometimes looking for a quick fix can get you into more trouble. Avoid anything that risks you getting further into debt. There’s no magic bullet here, but there are options to keep your head above water. Getting out of debt takes time, but a solid, steady plan that you can actually stick with will ensure it doesn’t take longer than necessary.

—Kristin

More Money Advice From Slate

Last summer, my wife’s mother died, leaving her a large house in a small town in Germany, which is where my wife grew up. She has no siblings, and her father died when she was a child. We met in Germany (I am American) and live in the United States, where we both have middle-class jobs. My wife now feels torn about what to do with her German property, because of a feeling of obligation to her mother’s memory. She had a tense relationship with her mother, who was often critical of her choices. Now we are discussing: should we fix up the house and rent it out? Someday retire over there? Both propositions scare me.

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