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 parents have spent their careers in noble professions that do not pay well. My dad is a social worker and my mom teaches kindergarten. They have lived a modest lifestyle sprinkled with treats I feel they deserve, like an annual vacation to New Mexico and enjoying some good wine. Recently, they experienced a few financial setbacks, neither of which was their fault. But now they can’t retire when they’d originally planned. My problem is with my fiancé.

His father was an insurance executive who stopped working at 55. My fiancé has said to me more than once that it’s a shame my parents “lived beyond their means,” which is why they can’t retire now, while his parents “budgeted and saved,” which is why they could retire. I have repeatedly tried pointing to the math: His parents aren’t thriftier, his dad just made $350,000 a year. My parents could have skipped every vacation of their married lives, and it wouldn’t have saved them as much as my father-in-law received in one average annual Christmas bonus. I am truly alarmed by my fiancé’s unwillingness to acknowledge his family’s fortune. How should I address this next time it comes up? We’ve known each other for a decade and this money talk is coming out of left field.

—They Weren’t Thrifty, Just Rich

Dear Just Rich,

Let’s start with the obvious: Your parents are technically upper middle class (with, I’m guessing, an income of around $100,000 per year), but life is expensive. They provided for their family and seemed OK with living modestly within their means. Unfortunately, financial setbacks happen, and retirement is no longer a guarantee for many families. It sounds like your family recognizes the reality of their situation. At some point, they’ll be able to retire, even if it takes a few more years to get there.

Now, let’s turn to your fiancé, whose boneheadedness is deeply concerning. Instead of explaining (again!) the math, start asking questions: Why is he comparing your families? Does he look down on people who can’t retire at 55? What happens if you and he face financial setbacks during your marriage? What are his financial goals? How does he define rich? Does he believe in saving every penny so he can enjoy an early retirement? If only one of you works, how does he view the balance of power in your relationship? Who gets to make financial decisions in your marriage? After you get through all that, you can express how sad his comments about your family make you feel. Then, listen.

This will be a difficult conversation, but I imagine you’ll learn something that will either validate your feelings about marrying this person or make you break up. Because at the end of the day, what he seems to be lacking is compassion for those less fortunate, perhaps shaped by his life of privilege. You were raised in a family that valued helping others. Unless you can find a way to align these critical values, you may want to rethink your engagement.

Dear Pay Dirt,

My mother is 65 years old and has been a widow for two and a half years. She has never had a lot of money, and has only worked odd jobs through the years due to a disability that is just enough to make it difficult to work, but not quite enough to claim disability. When her husband passed away, she was left with very little—just their house and the promise of some portion of his Social Security when she turned 65. The house isn’t paid off but is probably worth about $400,000; I believe she still owes about $100,000 and has an $800 a month mortgage payment. Still, the house is very old and sort of nickel-and-diming her at this point.

Now that she’s 65, she gets about $2,000 a month from her husband’s Social Security. Her 89-year-old mother also lives with her, and between my mom’s Social Security and my grandma’s retirement, they get by OK. My mom is very worried about when my grandma passes, and how she will be able to afford to live on just her Social Security (she’ll likely only get a small inheritance of maybe $20,000). She wants to sell her house and buy a mobile home in a mobile home park. She’s convinced that’s the only way she can support herself. But I’m worried that she doesn’t understand the value of equity, if she keeps her current home, to help support her long term; and that she only sees the short-term gain in her savings account if she sells it, buys a cheap mobile home, pays rent in the mobile home park, while pocketing $150,000 to $200,000. Based on her health and genetics, I’m hopeful she can be around for another 25-plus years. I don’t expect her to be able to support herself that whole time, and my brothers and I will be able to support her to some extent, but isn’t it better for her to continue to grow equity in a home with a low mortgage than to buy a mobile home that will never gain much equity?

—Long-Term Home Equity or Cash Now?

Dear Long-Term Home Equity or Cash Now,

I think your mother understands her situation perfectly. There’s nothing fabulous about having a lot of home equity if you can’t put food on the table or pay your electric bill.

Home equity is not liquid. If you never need to tap into it, home equity will continue to grow with every mortgage payment. When you die, your home can be passed down to the next generation with a significant tax benefit—a stepped-up basis. Your heirs inherit the property at its current market value, so if you sell it just after inheriting it, you won’t pay any long-term or short-term capital gains tax. But your mom is going to need cash to live on after her mother passes away. As she is living in the house as her primary residence, she will keep profits up to $250,000 tax-free when she sells. Let’s assume the house is worth $400,000 and she paid $200,000 for it. If she sold it today (and if you’re right about her remaining mortgage balance), she’d clear $300,000, which after expenses of sale would be around $280,000. If she puts that in the bank, and it earns 4 percent, she’d get another $11,200 annually in addition to her $24,000 Social Security payment. Not a lot to live on, so I understand her concern.

The big question is how much she actually needs to live on. Her biggest expenses going forward will likely be housing and health insurance. Those alone could eat up her $35,000 in income. Can she live with you or your siblings after her mother passes? Or can you and your brothers pitch in enough so that she can live independently?

Buying a mobile home seems like a good option on the surface, but it isn’t. You’re just buying a less expensive home, one that comes with a monthly rent payment that will rise every year. It will lock up her equity the same way her house does today. If she’s choosing between staying in the house with her $800 per month payment or buying a mobile home, then she should stay in her house. The nearly $10,000 per year she spends will be relatively affordable for her. But eventually, there will be maintenance and upkeep annually, with extraordinary expenses like replacing the hot water heater, a large appliance, or even the roof.

The best thing you can do right now is work with your mom on her budget. Find out how much money she has and work with her to draft a short-term and long-term solution that will make her feel comfortable that her resources will last for the rest of her life.

—Ilyce

Classic Prudie

I am married to a very smart, very calm man. We get along well, I’m a stay-at-home mom at the moment, and we have a lovely toddler. I, like a lot of moms, feel like a lot of my efforts are unseen, and it resulted in a fight the other night. It was nothing particularly toxic, but when he left for a meeting, he left his computer on…