I’m 35 and mortgage-free. My boyfriend, 55, wants me to move into his house and help pay off his mortgage. What should I do?

Dear Moneyist,

I’m 35 and have been dating a man 20 years older than me; he is 55. I have a 5-year-old child. Things were going well until we started having conversations about the relationship being serious and possibly merging our assets. 

He shared his home with his ex-wife after being married for 20 years. He recently took out a second mortgage on that home. He also has adult children in their late 20s, and they seem to still be heavily dependent on him for financial support.

He is repaying his own student loans, and also those for his children. I own my home free and clear. My student loans will be paid off within the next two years, and I made a few good investments so I have quite a bit of funds in savings and a good retirement account.

A standoff over the future

When we discussed taking steps to move the relationship forward and discussed marriage, I expressed that I would be willing to sell my current home, purchase a new home and asked that he do the same so we can build a life together. He was completely opposed to this plan. 

His ideal plan: I move into his current house that he shared with his ex-wife until he can pay it off, which would be in 10 to 15 years and then we could purchase a new home together. He also said that I could help him pay off his house to move the process along quicker. 

If we decide to go with his plan, his adult children will inherit that home. He’s not willing to compromise in this area, and it has created a roadblock in the relationship. I do not want to move into his home, and he says I’m being selfish and unrealistic.  

What should I do?


“Divorce can trigger a financial setback of 15 or 20 years, particularly when paying off a mortgage is concerned.”

MarketWatch illustration

Dear Anonymous,

He is the ultimate speed dater.

By moving in, assuming he pays his mortgage in full and adds your contribution to the pot, he will effectively halve the term of his mortgage. Put another way: You will effectively halve the term of his mortgage. You would be helping him build equity in his home. Nice work, if you can get it.

Divorce is economically devastating for many couples, many of whom end up splitting their assets 50/50, especially if they both started off in their 20s, had children and built a life together. It can trigger a financial setback of 15 or 20 years, particularly when paying off a mortgage is concerned. 

It sounds like your boyfriend kept the house and refinanced in order to pay off his ex-wife. That, plus the burden of these student loans has left him in a pickle. If you move in, rent out your home and pay him rent for the next 15 years, he’ll be free and clear by the time he’s 70.

That sounds like a very nifty plan. He’s proposing the “detergent and fabric softener in one bottle” answer to his post-divorce money problems: he gets a relationship with a woman who has all her budgetary ducks in a row and a tenant in a 2-for-1 deal. 

His plan is non-negotiable

His plan is more likely to succeed if he makes it non-negotiable, so now we have five problems. 1: The original proposal. 2: The lack of compromise. 3: His many student-debt obligations. 4: His response that you are selfish and unrealistic. 5: The 20-year age difference.

The last one is only a challenge because you are at different stages of your life. You are a young mother; his children are grown. You are on the road to fiscal freedom; he is climbing back into the black after a divorce. You have hearts in your eyes; he has dollar signs in his. 

There’s one thing I do like about this suggestion: you both remain financially independent. Whatever you decide, make sure this is a core tenet of any plan. You have your own home and a 5-year-old child to raise, so I caution you against buying a home with him.

Paying off your boyfriend’s mortgage should not be part of your retirement plan.

You can email The Moneyist with any financial and ethical questions at qfottrell@marketwatch.com, and follow Quentin Fottrell on X, the platform formerly known as Twitter.

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‘I cashed in my retirement account to buy our home’: My husband left me and our two kids and won’t pay the mortgage. What now?

My wife and I bought a beautiful lakeside home for $700,000. It’s now worth $1.2 million. Do we sell now to avoid capital gains?

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