Dear Penny, I will have been with my partner for 50 years…
Browsing Tag
dear penny
28 posts
Dear Penny: My Sister Is Broke Due to Her Freeloading Sons. Do I Help Her Anyway?
Dear Penny, My sister left her husband and moved into the city…
Dear Penny: My Dad Spends Up to $30K/Month. Could I Be Liable for His Debt?
Dear Penny, A few years ago, my parents got divorced. I’m in…
Dear Penny: How Do I Motivate My Boyfriend Who’s Refused to Work for 4 Years?
Dear Penny, My boyfriend of eight years stopped working four years ago.…
Dear Penny: My Handyman Says I Should Tip Him $20/Job. Seriously?
Dear Penny, I had a handyman with two helpers do remodeling in…
Dear Penny: Can I Pay My Wife So She Can Get Bigger Social Security Checks?
Dear Penny, I’ve earned more than the Social Security income limit for…
Dear Penny: I’m Getting an Inheritance, but Grandpa Forgot About My Sister
Dear Penny, My grandfather worked hard his entire life and eventually became…
Scared of Trading Bitcoin? Cash App Isn’t
The way people bank, invest and manage money has changed rapidly over…
Dear Penny: Should We Cut Out Kids’ Sports if We’re Always Broke?
Dear Penny, We are a two-parent household with three children under 10.…
Dear Penny: My Boyfriend’s Debt and Crypto Loss Cost Me $48K. Can I Trust Him?
Dear Penny, My boyfriend of three years now has charged up $10,000…
Dear Penny: How Do I Kick Out My 32-Year-Old Daughter After 2 Years?
Dear Penny, I have a 32-year-old daughter who seems to think that…
Dear Penny: Are We Jerks if We Don’t Pay $600 for My In-Laws’ Housecleaning?
Dear Penny, My husband’s parents have always expected their adult children to…
Dear Penny: Should I Tell My Daughter She’s Cut Off at 18 Now or Wait?
Dear Penny, I’ve decided to basically cut off my daughter once she’s…
Dear Penny: My Brother Owes Me $6K. Should I Forgive the Debt or Sue Him?
Dear Penny, My brother owes me over $6,000, and he is taking…
Dear Penny: Do I Have to Send a Gift if I Was Uninvited From a Wedding?
Dear Penny, I need some insight into today’s wedding protocol. My sister’s…
Dear Penny: Can My Daughter Inherit Life Insurance if She’s Still a Minor?
Dear Penny, I’m a single mother, and I’m trying to best plan…
Dear Penny: I Refuse to Sign My Boyfriend’s $5,000/Month Mortgage. Am I Wrong?
Dear Penny, My boyfriend’s mother passed away in April 2022. In 2000,…
Dear Penny: Is My Underachieving 52-Year-Old Boyfriend Using Me?
Dear Penny, My boyfriend is a bit of an underachiever. He’s 52…
Dear Penny: Can My 17-Year-Old Grandson Invest in a Roth IRA?
Dear Penny, My 17-year-old grandson is working after school and putting half…
Dear Penny: Can I Keep My $150K Inheritance Secret From My Kids’ Dad?
Dear Penny, I have inherited $150,000 from my father. What can I…