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

Dear Pay Dirt,

“Jon” and I have been dating for over a year and everything with just us is as perfect as it could be. But the more I learn about his family, the more second thoughts I have. His family is hugely wealthy, but there’s a catch.

Jon’s family is basically ruled over by his grandmother, “Rita. ” Rita is ludicrously, fantastically wealthy. Some she was born into, the rest she married into. She’s widowed with five children, all of whom have children of their own. Some of these people have been independently successful, but none hugely so. Thus they’re heavily dependent on Rita for anything beyond the basics when it comes to homes, education, weddings, vacations, medical bills, and other major expenses.

In return, Rita calls 100 percent of the shots. Members of Jon’s family have concealed their gender identities, orientations, and politics to avoid displeasing her. They’ve changed their education and career plans. One family member and their partner were happy with one kid, but had two more because Rita thought they should. Another had an unplanned pregnancy and was going to marry her boyfriend, but instead broke up with him and had an abortion because Rita thought she should. A teenage child right now is being forced to live as the wrong gender because their parents need Rita’s money for their special-needs sibling. Rita apparently has lawyers on retainer to change her will on a whim anytime anyone does anything that makes her feel they deserve more or less inheritance.

I don’t want to live this way, and Jon seems like he could be convinced to tell Rita where to go…but I also hate the thought that we could see his siblings and our hypothetical kids’ cousins end up ludicrously, fantastically wealthy while we have the typical shrinking-middle-class struggle, just because they played Rita’s game and we didn’t. I just want to be as far away from the whole mess as possible, so I can pretend people like this don’t exist. Going into medical bankruptcy or watching my kids have to choose lesser schools and smaller dreams would not hurt as much if there was no way things could have been different.

Jon and I have been talking about moving in together when my current lease ends…but I can’t help thinking this would be a step toward a life I already know I don’t want. Is this reason enough to break up with an otherwise amazing guy?

—Disloyal Subject

Dear Disloyal,

This woman is using her wealth to control and manipulate others, and I understand your impulse to want to distance yourself so you don’t get swept up in that. It’s also wise to anticipate how this will play out for you and relationship as you get more involved in this family dynamic.

You’re not just worried about money. You’re worried about raising kids who watch people around them compromise themselves, and others, for comfort.

And already, you’re afraid of choosing principle over privilege, of being the only ones who say no to the golden handcuffs, and then having to watch the consequences play out across your future. You’re already imagining a future where you’re resentful, isolated, or silently mourning what could’ve been. That might be reason enough to walk away or at least slow things down.

Help! What My Wife Said to a Kid Using Chopsticks Was Mortifying. She’s Always Doing This. I Saw Myself as an Honorary Aunt. Turns Out I’m Actually the Nanny. We Just Had a Baby. My Husband’s Visitation Rules Are Impossible to Bear. Help! My Ex-Wife Insists on Coddling Our Daughter. It’s Led to Dire Consequences.

All relationships have challenges. The question is: Are you up for this particular challenge? And is it something you and Jon are willing to work through together, or is it going to drive you apart over time?If you love him and can imagine going through hell with him and still feeling like you made the right choice, then maybe it’s worth having a brutally honest conversation to understand if he is truly willing to stand on his own and do things differently from the rest of the family.  If Jon shares your values and is ready to stand up to the family pressure, that’s a good sign. But if he’s hesitant or unwilling to set boundaries, you will finding yourself caught in the same moral bind, with higher stakes as the relationship continues. Ultimately, it’s about what kind of life you want to build, and whether you can imagine building it with Jon despite his complicated family dynamics. Talk to him. And then trust yourself to make the choice that honors both your values and your peace of mind.

—Kristin

More Money Advice From Slate

My partner is admittedly bad with money. He’s been out of work for a while and has been living off savings. I know he has debt, which he’s looking to clear with some inheritance, but he won’t tell me how this debt accrued. He was recently the victim of a scam. I tried to warn him, but his desire to get out of his current situation overrode his best judgment, and he shut down my advice. Now he’s a few thousand dollars down and devastated. We had talked about moving in together, but I recently also lost my job, and my trust in him and hope for our future have been shaken.

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