Next steps in career, relationship are tangled together

Q. My boyfriend and I have lived together for three years. Since we aren’t interested in having children, there’s not a lot of distinction between how we live now and what living together would be like if we were married. Our relationship is pretty solid.

We live in a remote area where we both have decent-paying jobs that allow us to live comfortably. The problem is, I’ve reached the top of my career with my current job, making it a dead end. Because we live in a remote area, there are no better jobs to switch to. In order to move up with my current company, we would have to move. My boyfriend doesn’t want to do that.

He suggested I freelance. I think I could do well, but I don’t know that for sure. I also know I would make little to no money while starting up. He said he would “pay for things for a while,” including rent, food and bills.

He’s keen on me being happier than I am in my current job, and he also wants me to have more flexibility so I can travel with him more often. He earns significantly more than me, has more assets, and doesn’t believe it would change his quality of life to foot more of the bills. But I see challenges.

What if he gets tired of paying for everything and thinks I’m not working hard enough? What if I want to buy something like a new jacket, and he resents me asking?

What if he wants to go to dinner, and I can’t afford it? Does he pay? Do I not go? Is it a bad situation to be supported by someone I am not married to?

A. It’s easy to answer this letter in a flip way and point out this sort of dilemma is exactly why some people get married. But on second thought, that’s not so flip.

Your boyfriend is asking you to make significant and risky financial changes, ones that will, at least in part, benefit him. At the same time, he’s not offering to assume any of the long-term consequences should things ultimately not work between the two of you.

In a worst-case scenario, you could be left in a severely financially compromised position, with little in the way of legal recourse should either of you want to end your romantic partnership. It’s not just that he could come to resent the financial pressure. What if you want out, but can’t afford to leave?

A cohabitation agreement drawn up by a lawyer, outlining the support you are due should the relationship end – whether you decide to ultimately marry, or simply continue living together – would go a long way toward offering you the financial protection you need.

But such an agreement won’t cover everything. It won’t, for starters, make the geographic and employment issues magically vanish. So there are a few questions I would ask you to contemplate before you make any decisions.

First, what do you want? Would you prefer to stay with your company and relocate, and taking this career risk is simply a way to keep your boyfriend happy? Or are you really tired of the grind? You don’t say.

Second, where do you see this relationship, say, five years out?

Only after you’ve answered those questions can you make some kind of decision about how to proceed.

To ask Helaine a question, email her at askhelaine@gmail.com.