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

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…