The Top 10 Dear Penny Columns of 2021

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Dear Reader,

As the clock ticks toward the new year, I’m looking back at the 10 most-read Dear Penny letters of 2021. Some big themes in my inbox from the past year:

Want some advice on a money dilemma? No question is too awkward or tricky. This column is a judgment-free zone, and I’ll always keep your identity anonymous. Send your money questions to [email protected]. Check back every Wednesday and Sunday to see if I’ve answered your question.

Keep those letters coming in 2022. Have a happy and safe new year.



Top 10 Dear Penny Columns of 2021

These were the 10 most popular Dear Penny columns of 2021.

1. Am I a Cheapskate for Not Giving $500 for My Aunt’s Funeral?

Dear Penny,  

My aunt passed away. Her only daughter, Beth, could not afford the full cost of the funeral. She is 61 and working two jobs and sometimes three jobs to make ends meet. She has children who are in their 30s, but they struggle to make ends meet as well. 

My cousin, Mary, and her siblings were thinking about helping her with the cost of the funeral. They are close to Beth and have had contact with her throughout the years. My brother, Tom, sent a message to me and my other two brothers saying Beth might not be able to pay for the funeral. Both of my brothers chimed in that they would be happy to help in any way they can. 

This whole conversation made me feel uncomfortable since I had not had contact with Beth or my aunt in over 30 years. However, my aunt was my dad’s sister, so I understood why my brothers wanted to help. I remained silent and didn’t reply until I had a chance to think about it. 

Three days later I had not heard from my brother regarding the funeral arrangements so I went online and found out the details of the funeral. I decided to send Beth a Mass card, knowing she and my aunt were very religious. I felt the gift was appropriate for my relationship with her. 

The following day, I heard from Tom saying that Mary and her siblings decided to chip in $500 apiece to help out with the cost of the funeral. The full cost of the funeral was now covered. 

My brother went on to say that Beth would no longer have my aunt’s Social Security checks. (My aunt was living with Beth at the time of her death.) Tom was wondering if we would all like to contribute and send something. He said he was willing to match the $500 that my cousins were giving to Beth and asked if we would like to contribute $500 each. All my brothers agreed to do so. 

I told him I already sent something to Beth. I haven’t heard from my brothers since that email. I have always been frugal and it bothers Tom. It’s not a question of being able to afford it. To me, $500 is a lot to give to Beth considering we are not close and have had no contact in decades. 

This situation has kept me up for nights on end. I’m not sure if I did the right thing by not contributing the $500. Do you have any advice?


Read Penny’s response here.

2. Am I a Jerk if I Refuse to Pay for My Mother-in-Law’s Funeral?

Dear Penny,

My mother-in-law is 89 and in good health. The reason I’m writing is that in August 2019, my father-in-law died at age 88 from cancer. There are eight siblings in total. My husband is the oldest, and my sister-in-law is fifth and has power of attorney for their parents.

When my father-in-law was in the hospital, my husband spoke to his sister about financial needs. My sister-in-law and her husband have helped my inlaws for years but said they were tapped out. Later after speaking to me, my husband told me he was going to give them money to help toward funeral expenses. He gave them a check for $5,000, money taken out on one of our credit cards. 

My sister-in-law accepted the check but completely shut my husband out of participating in my father-in-law’s funeral mass. Even after my husband asked if he could say the eulogy, she informed him she was saying the eulogy and had already selected other family members for other participating parts. 

She had five pages to speak from, but she only mentioned herself, her husband and their dog on how meaningful our father-in-law was in their lives. She said nothing about her seven siblings, or the 13 grandchildren and 11 great-grandchildren. A lot of family and friends who attended remarked that the way she said the eulogy came across if she were an only child, instead of one of eight siblings. 

I’m expecting the same outcome for my mother-in-law’s funeral, except this time I’m going to tell my husband that we will not help with any funeral expenses. If he insists, I only want him to give $500 not $5,000. We did pay off the $5,000 in less than a year, but I don’t want us to be as generous to my sister-in-law in the future, even though it would be toward my mother-in-law’s funeral. 

I realize my resentment is obvious in my letter, but I do want us to do the right thing. What should we do?


Read Penny’s response here.

3. Do I Sue My Brother-in-Law for the $92K I Paid to Save His Home?

Dear Penny,

My brother-in-law’s home was being foreclosed on. I had money that I could access in an annuity account, so I paid the house off so they wouldn’t lose it. 

We have a signed agreement that he will pay me, but he has not paid me anything since last year. He still owes me over $92,000. I basically gave him a $100,000 interest-free loan. 

I don’t want to have to sue him, but his wife doesn’t think they should have to repay me. I have now lost over $50,000 in dividends that would have been accrued on my account in addition to the money they still owe me. Please help.

-Unlucky in Kentucky

Read Penny’s response here.

4. Am I a Bad Mom if I Don’t Co-sign My Daughter’s $800K Mortgage?

Dear Penny,

My 25-year-old daughter moved back home while I was taking care of my mom, who has Alzheimer’s. Because I wasn’t staying there, she never paid rent, but she did pay for internet and gas. 

Well, now things are progressing, and I will be selling my mom’s home. I am currently having a room built at my home, since she will be staying there as well. 

I have always helped out my kids as a single mom. But my daughter listens to her paternal grandmother, who sadly told her to have me co-sign on a mortgage for her even though she just started working and wants an $800,000 house. I told her NO.

I then said her grandmother knows that this is an unrealistic request. I’m about to retire in three years, if not sooner, and still have my own very manageable mortgage. I’ll have a pension and Social Security with only a leased car to pay for. 

Now they are thinking of asking me again in a year or so to co-sign. Am I wrong to tell her no? I’m also thinking about selling the house and moving with my mom back East where she grew up to be closer to her aging brothers and sister. 

Now my daughter is upset and says she won’t have anywhere to go if I don’t help her get a mortgage. Am I wrong to focus more on me and my mother at this time in our lives?

I’ve done all I can for my daughter, but I don’t like the guilt trip she and her dad’s mom are trying to put on me. I know she can’t afford an apartment by herself in California, but that’s not my fault either.

-Frustrated Mom

Read Penny’s response here.

Dear Penny

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5. Am I Obligated to Tell My Parents I’m a Millionaire at 22?

Dear Penny,

I’ve become the first millionaire in my family. I’m wondering if I should ever tell them or how would I go about even bringing it up. 

I’m 22 years old. I’m not sure how my parents will feel if I tell them about my wealth but don’t use it on them, since most of it is tied into investments. Any recommendations on what I should do and if I should wait? 


Read Penny’s response here.

6. Am I Entitled to $240K Cash Found in My Dead Brother’s Drawer?

Dear Penny

My brother passed away five years ago. He left a substantial amount of cash in a dresser drawer. When my other brother had to identify his body, he found the $240,000. 

He and his wife made the decision to create a narrative of their own, suggesting that my brother was a drug dealer, so they could justify keeping this money for themselves. Consequently, with the loss of my brother and the stress of knowing that keeping this money was wrong and sinful, my brother had a massive heart attack. 

Now it’s his wife making the awful decision to keep this money, while some of us family members are struggling to get by. She has always controlled my brother, and it’s terribly saddening that a person could be that selfish. Is there a legal way of having this money distributed fairly among the rest of us siblings? 

-Saddened Sister

Read Penny’s response here.

7. Will Social Security Tell Me When My Ex-Husband Dies?

Dear Penny,

My now-ex-husband is 13-plus years older than I am, and he earned more money over the course of his career than I did. We were married for more than 10 years, and I have not remarried.   

I have consulted a couple of Social Security planners. Because my Social Security benefits are greater than 50% of his benefits AND I am likely to outlive him by a decade or two, they recommend I claim Social Security ASAP on my own benefits and collect the much-higher survivor benefits when he passes.

When my ex applied for Social Security, he noted I was his wife at that time, and I have income taxes and a divorce decree as proof of our common-law marriage lasting more than 10 years, so I plan to provide that information to Social Security when I claim next year.  

My questions to you: Since he and I are estranged, will Social Security automatically notify me of his death, so I can switch to the much-higher survivor benefit? If not, how can I possibly know when to make the change?

Do you agree with the two Social Security planners that my best course of action based on our age and income differences is to claim my own benefits early and survivor benefits later?


Read Penny’s response here.

8. Who Pays for Dad’s Massive Debt When He Dies?

Dear Penny, 

Our dad states in his will that my sister and I are to inherit his house. We’re supposed to sell it and pay his sizable debts, and then we get to split any leftovers. 

Are my sister and I responsible for the debt that isn’t paid off from the sale of the house? Are we then financially responsible for his massive spending habits when he was alive? 


Read Penny’s response here.

9. My Dad Says I Owe Him $400/Month When He Retires. Is This Fair?

Dear Penny,

Within the last year as I’ve learned more about finances, I’ve realized that I grew up in a financially illiterate family, and so did my husband. Both of us grew up with poor but frugal parents, and our frugality has helped us manage so far. 

We have a credit card, but we pay it off every month. We’ve paid off our two used cars, and we pinched pennies to pay off our school loans before our two kids were born. We bought our first house in June 2020 and have a monthly payment of about $1,600, so the only debt we have is that mortgage. I am a stay-at-home parent and my husband’s salary is $70,000 before taxes, insurance, etc., is taken out. We currently have about $13,600 between our checking and savings accounts, and my husband has a 401(k) through his employer with a 50% match, which we use.

But here’s the rub: When I was in college, some of my financial aid fell through. I had to face the fact that I couldn’t afford to go back after that summer. I was distraught because I was young and dumb and could only think about missing my friends and boyfriend (now husband). 

I don’t remember how it got smoothed over, but it did. I was allowed to go back. Again, I was young and dumb and didn’t give it another thought.

Much later, I learned my father took loans in his name to pay for what my financial aid didn’t cover. He paid off those loans with his and my mom’s retirement savings. I didn’t realize this until it was already done. 

Now they are talking about retiring in the next few years. (The date keeps shifting, but currently they’re talking about 2025 at the ages of 69 and 68.) They are missionaries living overseas and plan to move to the U.S. to the same state my brother and I live in.

Because they currently have about $6,000 total to their name (no debt, but no other savings), my brother — who is financially better off than I — bought a condo this year and is renting it out until my parents retire. My understanding is that he and his wife had to juggle things to make this work. But they decided this real estate investment would help fund their own retirement someday, not just provide a place for our parents to live.

My father now wants me to help pay for his and my mom’s retirement since he helped pay for my college. The loans totaled $39,769, but he had to pay interest. At first he wanted us to pay back $45,000 split into monthly payments of $400 from the month they retire until the $45,000 is paid back after about 10 years or they both pass away, whichever comes first. 

Now he’s saying because of inflation, he wants us to cover “about three days a month of our retirement living costs — whatever inflated dollar figure that happens to be — for the first 15 years of our retirement, or until death. Whichever comes first.” That’s a quote from his email to me. He got that figure by taking their current monthly income, averaging 21 work days a month, and dividing it by the $400 a month, which is 3.3 days of their current income.

We’ve plateaued at our current savings level since buying our house last year. I realize we have a few years to prepare for paying $400 or whatever it will be a month, but I’m at a loss for what to do or where to start. I’m also worried that we aren’t saving enough for our own retirement. What if we end up with no options like my parents and hurt our own children’s finances in the future? 

I’ve been trying to learn about bonds, Roth IRAs, and so on. I’m so overwhelmed by how little I understand. 

This isn’t legal debt, but I still owe my parents. They won’t be able to live in retirement without my paying them back. My brother has already done so much by preparing housing and a used car for them. I can’t ask him for more. Plus, it’s my fault my parents don’t have retirement savings, not my brother’s.

Can you please help me decide what our next steps should be? Do we hire a financial planner to give us custom guidance? Do I need to read books and take classes to understand how to manage all of this since Google results are going over my head? 

I’m considering taking a part-time job so its entire income can go toward paying back my parents, but I don’t know if that’s the right move either. I can’t work full time right now because our kids are elementary-age, and paying for childcare would eat up nearly the whole salary.

And don’t get me started on my in-laws, who live in a different state. My father-in-law is incarcerated. My mother-in-law is living on only Social Security in my sister-in-law’s apartment. My sister-in-law is single with two elementary-aged kids and is working full time while trying to earn a teaching degree. We are wealthy compared to that side of the family. We want to help them too, but we feel stuck!


Read Penny’s response here.

10. 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? This is one neither of us knows how to navigate.


Read Penny’s response here.

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