Dear Penny: Should I Marry My Boyfriend if His Bad Choices May Bankrupt Me?

A woman tries to run away from a proposal as the man clings to her leg with a ring in his hand.
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Dear Penny,

My boyfriend and I have been dating for about two and a half years and living together for a little over half of that time. We have discussed getting married but are not engaged. We have no immediate plans. 

My biggest concerns about getting married are financial. We earn about the same amount of money and currently split most expenses like rent and utilities. I have two specific concerns. 

My boyfriend has a lot of delinquent student loan debt. He has worked with an attorney to make arrangements to pay the private student loans (which I believe were in collections by the time he addressed them), and I have helped him get started with the process of rehabilitating his federal student loan debt. 

I hope that this is not a big deal moving forward, and I don’t have a reason to believe we haven’t taken steps to address all of his delinquent debt. We pulled our credit reports somewhat recently and went over them. There were no surprises or unidentified tradelines/balances, etc. 

That being said, sometimes I feel that he does not take administrative things, like opening mail and addressing what’s important very seriously, so I worry that there could be future (but hopefully smaller in scale) issues that come up. I should also note that I probably do most of this administrative kind of stuff for him at this point. While I would prefer not to, it’s more likely to get done at least. 

Second, I worry in the long term about his health. He is a little older than I am and has had some health issues in the past. He seems to be doing well now. He assures me he would tell me if there was cause for concern, but I worry that things could take a turn for him at a relatively young age. 

I have heard horror stories about married couples losing everything after being faced with devastating medical bills or having to pay for assisted living or something like that. Is there a way to protect myself and things like my retirement savings against a scenario like that while still being married? Or is that impossible? 

I love my boyfriend and can see myself spending my future with him, but I wish he would take things a bit more seriously in terms of his financial and physical health. I don’t want to end up in financial ruin because of his failure to do so. 

P.S. I have implored him to be more conscientious about this stuff, but he is the most stubborn person I’ve ever met, so I’m not banking on major changes in these regards.


Dear C.,

Reread the postscript of your letter. Look specifically at the words “he is the most stubborn person I’ve ever met, so I’m not banking on major changes.” Because really, these are the only words that matter.

Love isn’t the only ingredient that goes into a successful partnership. A good relationship requires two people who can accept adult responsibilities. But it sounds like you’re the only adult in the room.

Dear Penny

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I’m not too worried by your boyfriend’s student loan debt or even the fact that he fell behind on payments. What’s concerning is that it seems like you’ve made his debt into your problem. Without you, would he have done anything to bring those loans out of delinquency? I have my doubts if he refuses to even open his own mail.

Your boyfriend’s medical issues are more troubling. Our health is never guaranteed, of course. Even a teetotaling vegan who runs marathons could develop medical complications at a young age. Substantial medical bills can put a spouse’s savings at risk.

One expensive option is to purchase long-term care insurance. Other strategies, like a Medicaid compliant annuity, could help protect your savings if he would require nursing care someday.

But I think the bigger picture is that you want to be with someone who makes a reasonable effort to stay healthy. You also don’t want to lie awake at night wondering if a bill went to collections because your spouse never bothered to open it. You want to be a spouse, not a parent.

All that said, even the most stubborn humans are capable of change. But real change doesn’t happen when people are comfortable. Your boyfriend is most likely to grow up if he knows he has something to lose — by which I mean you.

Think hard about what it would take to quell your anxiety about this relationship and tell your boyfriend what you need. Would paying bills together each month set your mind at ease so that you’re both shouldering some responsibility? Is there an unhealthy habit that you want your boyfriend to give up?

You don’t want to micromanage every decision your boyfriend makes. But it is reasonable to have dealbreakers. Your boyfriend can choose not to change. But the price of his stubbornness is that he doesn’t get to marry you.

Robin Hartill is a certified financial planner and a senior writer at The Penny Hoarder. Send your tricky money questions to [email protected].