Dear Penny: We’re in Love and Want to Travel Post-COVID, but He’s Too Poor

An elderly couple hold hands as they overlook an ocean view while on vacation.
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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’s been married twice and has four children. He is very close to his kids, grandkids and siblings. I have met them and they are good, decent people. He has lots of friends and is very outgoing.

He’s self-employed with a business next to his home. He works when he feels like it. He would like to live and work in New England for four months and spend the rest of the time in Florida, where I live.

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.  

He knows that I will never marry again and whatever money I have left will go to my children. When he is down here, he stays with me (he’s been with me six months, now). He buys half the groceries and many times pays for restaurants, so his monthly expenses may add up to $400. He does help around the house.  

Now that we have our vaccines, I went to visit my family, who live in another country. He decided not to join me, but he didn’t want to return home, either. 

I pointed out that this is his busy time for business and he should take advantage. But he says he has worked hard and it’s his time now to enjoy life.

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. My alarm bells would go off if you were telling me that your 30-something boyfriend only works when he feels like it and says now is his time to enjoy life. But from a 70-something? Not so much.

What I want you to do is think about the next trip you want to take post-COVID. Would you have more fun if you took it alone, with the comfort of knowing you didn’t foot the bill for him? Or would you enjoy it more traveling together, even if that means you’ll pay for most of it?

I feel like you’re assigning a level of urgency here that doesn’t really exist. He’s already been staying with you for six months in Florida. He’s not talking about selling his home in New England. No one’s begging for the other person’s hand in marriage. You can plan a vacation, knowing you’ll pay for most of it, without committing your entire retirement to traveling together.

I don’t think your relationship is doomed — and age is a very big factor here. My answer would be very different here if you were in your 20s or 30s. If you were building a home, a nest egg and a family together, your differences on money could be too difficult to reconcile, no matter how in love you were. But in your 70s, it’s a lot more realistic that you can keep your finances separate.

Whatever you do, don’t pursue a future with this man if you think you’re going to change him. It sounds like money just isn’t that important to him. That’s not a character flaw.

You don’t always fall in love with someone in the same tax bracket. That means one person often shoulders a greater share of the expenses. But if this relationship truly makes you happy, that’s a small price to pay.

Robin Hartill is a certified financial planner and a senior writer at The Penny Hoarder. Send your tricky money questions to [email protected].