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10 Most Read Dear Penny Financial Advice Columns of 2019


10 Most Read Dear Penny Financial Advice Columns of 2019

In 2019, you asked Dear Penny about mooching relatives, the mysteries of credit scores and how to bounce back when you’re behind on everything. You asked about retiring early, retiring with student loans and retiring with next to nothing saved. 

But by far the most commonly asked question was whether to pay off debt vs. do everything else.

These are the 10 most-read Dear Penny financial advice columns in 2019.

Keep the questions coming in 2020. Ask Dear Penny your tricky money dilemmas here and you could see your question answered in a future column.

The 10 Most Read ‘Dear Penny’ Financial Advice Columns of 2019

Here are your top 10 questions for Dear Penny in 2019.

1. I Helped My Daughter Buy a Car and Now She Won’t Make Payments

This mom made an expensive mistake when she helped her daughter buy a car: She signed for the loan, but put the car title in her daughter’s name — with the understanding that her daughter would take over payments. Three years later, her daughter still refuses to pay up, so she reached out to Penny for solutions.

2. My Family Keeps Asking Me for Money and It’s Bleeding Me Dry

Many of us would be willing to help out our families in their times of need. But what happens when your family keeps asking for more and more? That’s the situation this letter writer found himself in, so he reached out to Penny for help. 

3. We’re in a Deep Financial Hole. Is There Any Way Out?

The letter writer reached out to Dear Penny in a state of crisis: mounting bills she couldn’t pay, three small kids to care for, a car with shot brakes. “I’m really at a loss, and I’m having horrible anxiety over it. I don’t know what to do,” the letter writer wrote

4. I Paid Off My Car Early. Why Did My Score Fall 79 Points?

This letter writer made a savvy money move in paying off their car loan early — which is why they were so baffled when their credit score dropped. Read Penny’s explanation for why that might have happened.

5. I’m 54 With No Retirement Savings. How Do I Get Started?

This letter writer greeted their 54th birthday with a crushing realization — that they were quickly approaching retirement age but had no retirement savings. Here’s what Penny suggests the reader do ASAP to get themselves on the path to retirement.

6. My Fiance Was Laid Off. He’s Fine With Letting Me Pay the Bills Forever

When the letter writer’s fiance lost his job, they had to find a way to make ends meet using only her salary. Six months later, she’s tired of being the sole breadwinner, but her fiance accuses her of nagging whenever she asks him when he’s going to find a job. Read Penny’s advice for how the letter writer can productively deal with this difficult situation.

7. We Have Bad Credit. Is There Any Hope for a Debt Consolidation Loan?

This letter writer hoped a debt consolidation loan would help them begin the hard work of rebuilding their credit, but their credit is so poor they keep getting turned down. How can they get themselves out of this Catch-22? Penny has some ideas.

8. Should I Invest My $10K Savings or Use It to Pay Off Debt?

The letter writer has managed to save up $10,000 and now he wants to know: What should he do with it? Should he pay off debt? Invest? Here’s why Penny says he shouldn’t do either

9. I’m a Single Mom Making $60K a Year. How Can I Retire at 45?

This letter writer is 32 with a pretty ambitious goal: to retire in 13 years. While caring for two small children. And making $60,000 a year. Can she do it? Penny explains why this might not be realistic — and she also has some words about the FIRE (financial independence, retire early) movement.

10. A Heart Attack Put Me in Debt and Now I Can’t Get Out

This letter writer is one of the millions of Americans who landed deeply in debt due to unexpected medical expenses, and she’s tried just about everything she could think of to get herself back out. “I’m too embarrassed to tell my family or my friends, and I definitely don’t want to ask them for more money,” she writes. Penny offers the letter writer some advice — and some compassion.


Robin Hartill is a senior editor at Codetic and the voice behind Dear Penny. Send your tricky money questions to [email protected].

Deputy managing editor Caitlin Constantine contributed to this article.

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