Dear Penny: Is Your Relationship Doomed if One Person Earns Way More?

Two people who are not compatible sit awkwardly on a couch.
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You won’t always fall in love with someone in your tax bracket. That disparity is often a big source of stress in relationships, judging from the Dear Penny inbox.

You don’t have to be in the same place moneywise for a relationship to succeed. But having vastly different incomes or debt levels can be a dealbreaker if you can’t find a way to be equal partners. Here are four dilemmas about how to navigate love with someone who earns way more or less than you do.

‘My Rich Boyfriend Worries I’ll Burden Him if We Marry’

Dear Penny,

I’m a 35-year-old female who’s divorced, and my boyfriend is 38 and never married. We’ve been dating for two years, and it’s been wonderful. Recently, we’ve been having talks about our future, but money is a bit of a hang-up for him. 

He makes significantly more than I do (between four to five times as much), and he worries that my low income means I’ll be a burden on him when we get older if we decide to marry. The way I see it, I am very responsible with the money I do make. I don’t have any debt, and I pay all my own bills. 

I’m not asking him for anything, although I do understand that at this rate my retirement savings will be meager while his will be substantial. That could lead to problems if he wants to travel and not feel bitter about having to pay for me for everything later on. 

Do you have any advice for us? 


Dear R.,

It’s been a wonderful two years. You’re talking about growing old together. Then the conversation turns to how little money you make and how you might be a burden to your boyfriend later on.

That doesn’t sound wonderful to me. That sounds cruel.

Read the full column here.

Dear Penny

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‘We Want to Travel Post-COVID, but He’s Too Poor’

Dear Penny,

I’m 70 and a widow of six years. I was married for almost 43 years. Two years ago, I met a man from New England on a dating site who’s just a bit older than me. We’re both healthy and physically active. We love to dance, hike and visit new places.

He doesn’t have much money. His Social Security is minimal. He saves it and lives off of the money he makes from his business and the settlement his ex-wife sends him, which will end in two years. His house is paid off, his expenses are low, and he is careful with his money.

My husband left me financially secure. We were always careful with money and never lived an extravagant lifestyle. I’ve got two adult children who are financially independent.

The man I’m seeing doesn’t have much disposable income and isn’t concerned about it. I’m not sure about a long-term future with him feeling this way. When this pandemic is over, we’d both like to travel and do more, but I don’t want to travel on the cheap. I’m not talking about fine dining and five-star hotels. Just something in-between. I have no problem paying my share, but not for both of us.  

Is this relationship doomed because of our differences in attitude on finances? Should we just enjoy what we have?

-Am I Too Old to Have It All?

Dear Am I Too Old,

You found a guy who isn’t rich, but does he make your life richer? Your letter screams “yes” to me.

You share the same hobbies. You like his family and friends. It seems like he’s an equal partner with you, even though he can’t pay 50% of the bills.

Your boyfriend sounds like someone who manages what little money he does have wisely. He can afford his lifestyle — he just can’t afford your lifestyle.

Read the full column here.

‘Will My Huge Paycheck Scare Away the Men I Date?’

Dear Penny,

As a single girl in her late 20s, I make a more-than-decent living in an area where cost of living is relatively low. I’m making significantly more than the average person here, especially at my age.

As I’m getting more serious about dating, I’m finding that people of my generation are very upfront about their financial situations, and many of the men I’m dating are thrown by even the implication of the money I earn. 

With millennial-age individuals being more and more casual about discussing their financial status, at what point are you meant to disclose your income in a relationship? 


Dear K.,

Pretend you’re having the salary talk with a guy you’re dating. You go into the conversation expecting that you’ll be the higher earner. But then the man surprises you. How would you feel if he reveals he earns three or four times more than you do?

Read the full column here.

‘My Fiance Got Laid Off, but I Didn’t Sign Up to Be the Breadwinner’

Dear Penny,

My fiance lost his job nearly six months ago and got a decent severance payout. We used most of the money to pay off debt and have been surviving on my salary.

I make enough to pay our bills, but there’s very little left over for extras. We’re living like hermits, and we aren’t putting money aside for emergencies or our goal of buying a home.

My fiance doesn’t seem to think that this is a problem because we’re making ends meet. He isn’t looking for jobs, hangs out around the house all day and says he needed a break from working.

Penny, I never wanted to be the sole earner, and I hate living paycheck to paycheck. He tells me to stop nagging him whenever I ask him when he’ll start searching for a job.

How do I get him to understand how stressed I am about our finances?

-Squeaking By

Dear Squeaking By,

Try saying this: “I am stressed about our finances.”

Say it when you’re sober. Don’t say it after a hellish workday or in the middle of a fight over whose turn it is to scrub the toilet. Say it soon.

Read the full column here.

Have a question about love and money? Send it to [email protected]Robin Hartill is a certified financial planner and a senior writer at The Penny Hoarder.