Dear Penny: The 10 Trickiest Money Questions of 2020

In this illustration, a person scratches their head with a question mark above their head with money inside a bottle.
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Dear Reader,

Every week I seek out your tricky money questions — and boy oh boy, did you deliver in 2020. The year brought lots of questions about stimulus checks, unemployment benefits, hardship agreements and pretty much everything COVID-19-related. But just as in 2019, family money spats, retirement worries and catching up when you’re behind on everything were among the common themes.

Thanks for all the great questions in 2020, and please keep them coming in the new year. To ask a question, use this Dear Penny form or email [email protected]. (And don’t worry: I’ll always keep your questions anonymous.)

Cheers to a safe, healthy, happy and (hopefully) less tricky 2021!


Your 10 Trickiest Questions for Dear Penny in 2020

Here are 10 of the trickiest money questions you asked in 2020.

1. Do I Need My Ex-Husband’s Permission to Get His Social Security?

She married at 19 and divorced in her early 30s. As she prepares to retire next year, she’s thinking of collecting Social Security based on her wealthy ex-husband’s record. Does that mean she needs to contact him and get his permission first?

2. My Cheapskate Parents Won’t Tip for UberEats. What Can I Do?

This writer downloaded the UberEats app for her elderly parents. A few months later, she made a horrifying discovery: Her parents refuse to tip. Is there any hope of changing their rude ways?

3. I Was Unemployed for 5 Months. How Do I Catch Up on My Bills?

He just got hired after 100 job applications and five months out of work. The problem: He’s behind on all his bills, and his new job pays less than the old one. Is there any way he can catch up?

4. Should I Use My Savings to Pay Off My Boyfriend’s Payday Loan?

Her live-in boyfriend got a payday loan after a car accident and a death in the family, and now he can’t break the payday loan cycle. He hasn’t asked her for help. Should she offer up her emergency savings anyway?

5. Is My Husband Gambling Away Our Future on Robinhood?

Her husband suspended his 401(k) contributions so he can play day trader on Robinhood. He says she shouldn’t worry because he’s making big profits. Should she trust him?

6. I’m in College With $10K Saved. Should I Invest It All in Gold?

He’s a college student with $10,000 in the bank and $22,000 in student loans. He doesn’t know much about investing, but he’s worried the U.S. dollar will lose value. Does that mean it’s a good idea to invest his life’s savings in gold?

7. Is It Crazy to Go Back to College and Live on a Bus at 60?

This letter writer spent the last eight years as a caregiver. After receiving a large life insurance payout, she’s thinking of going back to college and renovating a school bus to live out of. Everyone else thinks it’s a terrible idea. Are they right?

8. How Do I Save Money When My Wife Refuses to Let Me Work More?

He wants more money, so he’s day trading and considering a part-time job or driving for Uber. But his wife is saying no to all of his money-making ideas because that means less time with the kids. Is there any hope of swaying her?

9. Can We Afford to Retire on Just $65K a Year When My Husband Retires?

Her husband is nearly 70, which means retirement is on the horizon. That means their income is about to take a hit. She’s filled with anxiety about their finances. Can they survive on a retirement budget of $65,000 per year?

10. My Car Lender Said I Could Skip Payments, So Why Are They Saying I’m Delinquent?

Her car lender gave her a hardship arrangement, which meant she didn’t need to make payments. Her credit report tells a different story — and the mistake cost her 56 points on her credit score and a $10,000 business loan. How can she fix the error before it destroys her finances even more?

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