18th May 2026

Dear Penny: Should I Pay My Boyfriend’s Bills if I Only Visit on Weekends?

I drive an hour every weekend to visit my boyfriend. I clean, take care of his dogs and pay for half of everything when we go out. Now he's saying I need to pay his utility bills. Is this reasonable?

18th May 2026

Dear Penny: Should I Cash Out My Retirement at 28 to Prep for a Stock Market Crash?

The stock market is basically gambling, so why shouldn't I cash out my retirement at 28 and pay off my mortgage?

18th May 2026

Dear Penny: Should I Date a Man Who Vows He’ll Leave Me Penniless When He Dies?

I went out on a date with a man with five children who says he's fabulously wealthy, but he plans to leave it all to the kids. That means if we married, I'd get nothing when he dies. Is that fair?

The Penny Hoarder • 5th March 2023

Dear Penny: Should I Change My Kids’ Inheritance for My Online Girlfriend?

I’ve been corresponding with a 53-year-old lady in Shenzhen, China. I’ve invited her to visit me in the U.S. I have a feeling we’ll fall in love. What’s a fair way to divide my estate between my grown children and future wife?

The Penny Hoarder • 1st January 2023

Dear Penny: Should I Tell My Daughter She’s Cut Off at 18 Now or Wait?

I’m cutting off my daughter after high school in five months. I could easily provide for her. We have a great relationship. But after living with my parents into my 20s, I believe in the School of Hard Knocks. Do I tell her now or wait?

The Penny Hoarder • 9th November 2022

Dear Penny: My Best Friend Died. Is Her Husband Liable for Her Secret Debt?

My best friend was killed by a drunk driver. I’m helping her husband sort things out. We discovered she was hiding credit card and student loan debt. Is he responsible for it?

The Penny Hoarder • 17th August 2022

Dear Penny: My Husband Refuses to Pay for the Costs of Raising Our Kid

My husband makes twice as much as me, but he refuses to pay for anything for our child. Not school supplies, clothes, classes or gifts. I’m always broke as a result. What should I do?

The Penny Hoarder • 22nd May 2022

Dear Penny: Can My Deadbeat Son Fight My Decision to Disinherit Him?

My son has stolen from me for years. He even breaks in when I change the locks, so I’m leaving everything to my sister. Can my son fight my decision in court when I die?

The Penny Hoarder • 4th May 2022

Dear Penny: Should My Husband Refuse to Pay $600 for His Mom’s Cremation?

My husband spent $450 on airfare after his mother died. His brothers live nearby and didn’t have to travel, but they sent him a $600 invoice for a third of the cremation. Money is tight. Can we refuse to pay?

The Penny Hoarder • 22nd April 2022

Dear Penny: Was I Wrong to Give My Daughter’s College Fund to a Relative?

When my daughter didn't go to college after a gap year, I used her college fund to pay off a relative's student loans. Now she’s posting about “deadbeats” who won’t support themselves. She lives at home rent-free. How can I change her attitude?

The Penny Hoarder • 10th April 2022

Dear Penny: Can I Kick Out My Boyfriend if We’re in a Common-Law Marriage?

After seven years, my boyfriend and I moved in together. We bought a house that’s in my name only. Now I want to dump him, but he says I can’t kick him out because we’re in a common-law marriage. Is he right?

The Penny Hoarder • 30th March 2022

Dear Penny: Am I Responsible for My New Husband’s Secret $200K Debt?

I’m 59 and recently married. I just learned my new husband has over $200,000 of debt. Am I responsible for the debt, even though he brought it into our marriage?

The Penny Hoarder • 13th March 2022

Dear Penny: Can I Stop My Ex-Wife From Claiming Half My Social Security?

I was married 22 years. The marriage ended in 2002. When my ex-wife retires, will I be able to collect half of her Social Security? Can I stop her from coming after half of my Social Security?

The Penny Hoarder • 9th February 2022

Dear Penny: Do I Have to Pay Mom’s Debt With My $1M Life Insurance Payout?

My mom died deeply in debt. She told me to walk away from her estate and not tell anyone of her death. She also left me over $1 million worth of life insurance. Am I on the hook for her debt?

The Penny Hoarder • 30th January 2022

Dear Penny: I Can’t Afford a Divorce Lawyer. Am I Stuck With My Wife Forever?

My wife and I haven’t been intimate in 10 years. The sound of her voice drives me nuts. I want a divorce, but I’m afraid I’ll wind up homeless. I can’t afford an attorney. What should I do?

The Penny Hoarder • 24th November 2021

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

My dad never told me he took out personal loans to pay for my college. Now my parents have just $6,000 to their name. Is it fair that he now expects $400 a month from me when they retire?

The Penny Hoarder • 26th September 2021

Dear Penny: Was My Cousin Allowed to Buy Life Insurance on My Mom?

My mother died after several years with Alzheimer’s in the Philippines. While she was living in Maryland, a cousin took an insurance policy on her. Now my cousin is asking for four death certificates and wants me to fill out forms because, according to her, I am the beneficiary. What is she trying to do?

The Penny Hoarder • 22nd September 2021

Dear Penny: My Mom Keeps Dressing Like a Landlady and Threatening to Evict Me

Not wanting to freeload, I suggested that my mom charge me rent. Sometime later, she appeared in a rather formal outfit, and said she was now my landlady. She spelled out my rental rate and terms; it was higher than I had planned on, but she conveyed such an air of authority that I didn't argue. Later, when she was back to her normal self, I told her the rate was too high. She stepped out and returned as the “landlady,” and asked what the problem was.

The Penny Hoarder • 26th July 2020

Dear Penny: I Got Laid off at 62. Should I Retire and Take Social Security?

I turned 62 right when the first Covid shutdowns were happening, and guess what I got as a birthday present: a layoff. Should I start collecting Social Security now or hope for a miracle in this terrible job market?

Florida's favorite paper, Tampa Bay's favorite local news site • 6th December 2019

Dear Penny: I don’t owe anyone money ... but I also don’t have a credit score

If you don't use credit for 24 months or more, you could become "credit invisible," meaning you won't have a credit score.