I’m in my 50s and divorced with a $1.7 million home. I fell in love with an old school friend. Does it make financial sense to marry?

Several years ago I was happily divorced. Checking in with an old friend, a woman I’d known in high school and college, the damndest thing happened: We fell in love.

We are in our late 50s and we will be together for the rest of our lives. It’s a great relationship. The company she works for is fully virtual, and she spends about half the year with me. I visit her for a week or two at a time during the off months. She has two adult kids, and I have one in college and two high schoolers who rotate between my house and staying with their mother, who lives around the corner.

I wonder about the financial trade-offs of staying unmarried. When in the past we have discussed the issue, our answer has always been, “Why ruin a good thing?” We are both artists and a bit rebellious when it comes to things like that. At the same time, we see the advantages that marrying would confer — say if we were to just send in the paperwork and then stick it in a file somewhere. I would like to know what is really at stake in our decision.

Here are our details: I am a college professor and will likely work for the next five or six years in order to get my state pension (yes, they still exist) up to a reasonable, if mediocre, level. I make about $105,000 a year right now and live in an expensive city in an expensive state. I have a mortgage balance of $600,000 on a $1.7 million house. I have a $500,000 Roth IRA, a portfolio account of $500,000 and $300,000 in 529 plans for my three kids, one of whom is a freshman in college, while the other two are a senior and a freshman in high school.

My partner has two adult children. She earns about $180,000 per year and has investments of around $200,000. She also owns a house worth perhaps $600,000, with a mortgage balance of around $300,000. One of the issues I’m curious about is health insurance. We would likely free up anywhere from $300 to $600 per month by being on the same plan. Another is our tax status. I have filed as head of household since the divorce. She has filed as single for the last year or two.

And then there is the issue of retirement. I plan to retire as early as possible, as I expect to have some income from investments. I might also rent out the back building on my property, and I might inherit a small amount. Once my youngest is at college and I am retired, my partner and I would be free to live together full time. If I am using my employer’s calculator correctly, my monthly retirement benefit would either be around $4,000 with only the balance of contributions going to my beneficiary, or around $3,600 with an equal amount going to my beneficiary.

I don’t know my partner’s situation. I think she has a 401(k). So at this point, it seems like getting married is smart, and assuming one of us will outlive the other, it makes sense for me to choose a plan with a monthly benefit going to the beneficiary. Then there are all of those issues like who makes health and end-of-life decisions. How should we evaluate those potential benefits?

Furthermore, there must be issues I’ve missed. What else should we be thinking about?

Insert Catchy Pseudonym Here

Related: My late husband’s parents left me nothing in their will. Am I wrong to think they are thoughtless?

You’re a good catch, but forever is a long time.

Financially, she has more to gain from marrying in the long run, but you could both end up saving thousands of dollars a year in taxes and healthcare costs. Still, you just recently got out of a marriage, so my hope is that you enjoy being legally single and don’t sign another marriage contract quite so soon. And please, if you do, don’t just do it for financial reasons.

I recommend a prenuptial agreement and full financial transparency. Given that you’re both in your 50s and you, at least, have substantial assets in the form of retirement funds, this is especially important. As a married couple, you will benefit from income-tax breaks and Social Security allowances (including spousal benefits and survivor benefits).

Be aware that spouses can claim an elective share of their late spouse’s estates in many states; a good prenup could help override such state law. If you married and filed jointly, you would probably save around $6,000 to $8,000 on your federal income taxes. State taxes will vary, depending on where you live.

However, these income-tax savings could be wiped out on your children’s Free Application for Federal Student Aid, which is used to apply for financial aid to help pay for college. Together, your salaries will likely affect your children’s eligibility for federal, state and college-based aid, including grants, loans, work-study programs and scholarships.

Ultimately, getting married — preferably after your children are out of college — makes financial sense as long as you make sure your legal and financial contract is as rock-solid as your (current) romantic one. The financial savings could equate to $15,000 or more annually on your health insurance and federal taxes alone.

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This is not quite a relationship of financial equals. Your girlfriend earns more, but you appear to have done a much better job of saving. You both have homes, you both have children from previous marriages to whom you will presumably leave your assets, so discuss your respective expectations to avoid a years-long financial fallout like the one faced by this couple.

Your (financial) reasons for marrying would also depend on whether you plan on leaving your wife a large portion of your estate if you were to die before she does. You have a $1.7 million house and $1.3 million in investments. If you married, she would get a step-up in basis on those assets, potentially saving roughly $500,000 in capital-gains taxes.

Living together is not the same as dating, and you will have to deal with the realities of each other’s daily lives, including how adult children fit into the mix. Sharing a house with a third adult may be both a gift and a challenge. You may like the balance you have now between time alone and time together. Will living together full-time change that?

At age 62, you are entitled to collect up to 50% of the amount of your ex-spouse’s Social Security benefits, if they are greater than yours. To qualify, you must have been married for at least 10 years and be unmarried at the time of your application for spousal benefits. If you both have adequate Social Security benefits, that will be of little concern for you.

There are other financial advantages to getting married later in life: Maintaining one home is obviously far less costly than maintaining two. But you can’t put a price on financial independence and, if your partner moves in with you, I would recommend to her (if she wrote in) that she rent her home rather than sell it.

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There are downsides as well, aside from domestic issues like sharing a bathroom. These include the cost of medical and long-term care if one partner falls into ill health — which could be as high as $10,000 a month for an assisted-living facility — as well as disputes over inheritance and, as you have already discovered, the price of a divorce lawyer.

Looking ahead, you should also think about Medicare benefits. “Each spouse pays separate Medicare premiums, and married couples don’t get a discount,” according to AARP. If both spouses are enrolled in Medicare Part B, they each pay $185 a month in 2025 – and that goes up for couples with higher incomes.

Being married and enrolled in Medicare has benefits as well as drawbacks, AARP adds. “You can qualify for premium-free Part A based on your spouse’s work record. Most people don’t pay premiums for Medicare Part A because Medicare taxes were deducted from their paychecks for at least 40 quarters of work, the equivalent of 10 years or more.”

And the bad news: “Joint income affects premiums for high earners,” AARP says. “People with high incomes pay more for Medicare Part B and Part D prescription-plan premiums, and the high-income surcharge is based on joint income for married couples filing a joint income-tax return.” Read more about that here.

As you can see, getting married is like running a business. It’s financially complicated and, whether you live in a community-property or an equitable-distribution state, you will probably end up mingling some of your assets. But there’s no need to fly to Las Vegas just yet. Given your recent divorce, I suggest a very long engagement.

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Previous columns by Quentin Fottrell:

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I received an inheritance from my father’s estate, but the executor wants me to give it back. What should I do?

‘Luckily, I did not mix our finances’: My husband is 7 years younger and has dementia. What happens now?