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

Dear Pay Dirt, 

My younger sibling and I grew up in the same house, but with very different monetary lives. Until our mother’s death several years ago, she subsidized my sibling’s lifestyle substantially while refusing to give or lend me much of anything. Now, though, I have several advanced degrees, a profession I’m proud of, and a modest but steady financial life. My sibling is … a whole other story.

They are 30, have a bachelor’s degree and several certifications for various professions, but they haven’t committed to a single field. They haven’t held a steady job for more than a few months, and they’ve never had a full-time job. They have also spent months at a time out of the workforce voluntarily. Our dad generously sends us each about $15,000 a year, and I suspect my sibling benefits from significant help from the government for food and health care.

Eventually, we will likely get inheritances, but nowhere near enough to live on for the rest of our lives. To their credit, my sibling has never asked me for money. But I am afraid that as we get older and near retirement, reality will begin to settle in, and I may be one of the few people they can turn to when they realize their inheritance is gone and they have no retirement savings.

I will admit our different upbringings and our different lifestyles have left a bitter taste in my mouth. Do I have a responsibility to tell them sooner rather than later that I will never be willing to help them financially, even if it harms our relationship? They have plenty of time to turn their lives around, but there is no indication they are interested in doing so.

—No Help

Dear No Help,

You may be putting the cart before the horse here. Sure, there are signs that your sibling isn’t doing a stellar job handling their finances, and you might even be right that there’s a good chance they’ll hit you up for money down the road. But are you truly trying to get ahead of a potential problem, or are you hoping to vent to them about your resentments?

I ask because it sounds like you have a lot of built-up animosity about their financial situation. And maybe that resentment is warranted, but I suggest dealing with it carefully and thoughtfully. Start by taking some time to think about your own true feelings about this situation. As you say, all of the issues you raise here—from your mother’s support of your sibling, to your inheritance, to your career choices —have left a bitter taste in your mouth. Get to the bottom of that. How does it feel? Do you wish things would have been different with your mother? Are there unresolved issues there? Do you wish you could take more time off work? Are you feeling burnt out or uninspired? Get to the root of what’s really going on here for you.

Because ultimately, these are issues that aren’t going to be resolved by telling your sibling you won’t fund their retirement. That might just start a fight, and maybe there’s a part of you that’s hoping to do just that, because then you can get some of this off your chest. If you do want to have a conversation about retirement with them, try approaching it with curiosity. For example, “I’m curious what your retirement plan is. You’re my sibling, I care for you, and I want to make sure you’re able to support yourself in the future.” That much is easy. The harder conversation might be addressing all the ways you believe things are unfair for you .If you bring this up to them, be clear about what your feelings are and where you stand. Don’t make it their problem. Talk about how you feel without blaming them for it. But let them know this makes retirement a tricky issue for you. You’ve worked hard and made sacrifices. You want to be there for them, but you also don’t want to be asked to do something you believe is unfair. The bottom line: the two of you have some unresolved issues, and rather than cut them off before they’ve even asked for something, it’s a good idea to get to the bottom of those issues and lay out your expectations for the future. And that may just help you come to terms with the past.

Please keep questions short (

Dear Pay Dirt, 

I am 26 and engaged. We rent a one bedroom apartment. I work nearby while my fiancée commutes. Her sister is a single mom. She was driving a car older than she was, but it finally gave up and she couldn’t afford a car payment.

My fiancée “sold” her older car to her sister and she drives my brand new one. It is my first real independent purchase, so I do baby my car. I keep it immaculate and don’t allow smoking or eating in my car. And no one drives it but us. My fiancée agreed to my rules when she gave her old car to her sister.

Well, I was gone for a week. Her sister’s car was having mechanical issues, so my fiancée loaned her my car. In a matter of four days, it got completely trashed. Food smashed into the seats, mysterious stains, everything was sticky and gross, and the passenger side was literally filled with leftover take out trash. Her sister just left it like that in our parking lot. It was the first thing that greeted me when I got home.

My fiancée was asleep when I got in and we had a fight. I wanted to know what the hell happened to the car, and she just casually confessed to breaking every rule we agreed to. Her argument boiled down to her sister is a single mom who has it hard and she knew I would object. I took the car to be detailed and then sent the bill to her sister. Her response was so much profanity that I had to block her number.

My fiancée was furious with me. We had another big fight where I told her that her sister was disrespectful and disgusting. She didn’t even bother to take the trash out, let alone vacuum the car. If her sister wrecked the car, did she think she would pay for the damages if she wouldn’t pay this bill? My fiancée said that didn’t happen and was beside the point. She said it was her car too, and I couldn’t control what she does or where she goes with it. I pay the car payment and the insurance. My fiancée locked me out of the bedroom and wouldn’t even let me grab my toothbrush or sleeping bag. We only have a love seat and a recliner in the living room. She yelled through the door that I could sleep on the floor.

I grabbed both sets of keys and my gym bag and went to a motel.I got woken up by my fiancée screaming that she was going to be late to work and where was the car? I told to her to take an Uber. I went back to the apartment and packed a bag and stayed with friends for a few days. Our tempers cooled down and we both apologized, but I am not letting her drive my car again. Her sister hasn’t apologized and just doubled down that she did nothing wrong because “kids are messy,” and I am “an abusive control freak.” My fiancée keeps defending her sister, and it just makes me trust her less. I left the car at my mother’s and my fiancée has been getting rides from coworkers or taking Ubers. She hates it but doesn’t want to get a car herself.

Half our friends think my fiancée was in the wrong, but I took it too far. Some tell me that this is a big red flag that she puts her sister first before me. My mother told me that I should use this as a litmus test for how our marriage will be. She feels my fiancée is too emotionally enmeshed with her family to act as a proper partner.

I don’t know what to feel. I usually stay back when my fiancée deals with her family, but I think this might be a deal breaker. I need some outside advice here.

—Deal About The Car

Jamilah Lemieux
My Ex-Husband “Punished” Our 5-Year-Old for Discovering His Affair. I’m Livid.
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Dear Deal, 

Wow, there’s a lot going on here. I have to agree with your friends who are putting the blame on you both. Yes, your fiancée knew that your car was important to you, and yes, she neglected to take care of it while you were away. But the fighting that erupted afterward? To me, that’s the real  issue, and it involves both of you. You and your fiancée need to learn to deal with relationship conflict. Because if you’re having this much trouble working through a problem with a dirty car, it’s not a great sign for things to come.

Help! My Husband Found an Envelope Full of Cash. What Happened Next Might Ruin Our Marriage.

My Cousin Told Me About a House He Wanted to Flip. I Accidentally Bought It.

Help! My Best Friend Has Always Wanted Us to Have Babies at the Same Time. Well, I’ve Been Lying to Her for Years.

My Niece Survived a Bomb Blast, But It’s Her Romantic Life That’s Freaking Me Out.

In an ideal scenario, this would have played out much differently. You would have reflected on your feelings upon seeing your car in disarray and communicated those feelings to your fiancée after you calmed down. Then she would have responded with empathy, and the two of you would have come up with a solution together. If you’re not used to communicating this way, it can take time and work to learn better habits. I strongly suggest talking to a couples therapist who will give you the tools you need to work through issues like this—tools like active listening and using “I” statements, for example. A therapist can sit with both of you and show you how to use these strategies in practice.

In even the strongest relationships, couples butt heads sometimes.Life happens, you don’t always see eye to eye, and you’re not always going to be on the same page. You and your fiancée have an opportunity to learn some better conflict resolution skills and give them a trial run before you get married. If the two of you can work through this together, you’ll build a healthy foundation for the future. (And even if you do call it quits, I encourage you to do this work on your own. All relationships have conflicts.)

—Kristin

Classic Prudie

I have been dating “Diane” for several months. She is 24 and has a four year old son “Stevie.” She lives with her parents and works full-time. I enjoy spending time with her and her son, but she has this nasty habit of forgoing arranging child care and just dragging her son along on our dates. These are always activities I have arranged weeks in advance and are not child friendly, like kayaking (we never got in the water) or parties with my friends (my friend had a board game party and Stevie ended up using his markers on the wall). Diane always claims her sitter backed out at the last minute and she had no choice, but I find it hard to believe that it happens so often.

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