Dear Penny, I will have been with my partner for 50 years in July, but we’re not legally married. Can I receive his retirement when he dies? I’m…
Read more Dear Penny: Will I Be Left With Nothing When My Partner of 50 Years Dies?Dear Penny, My sister left her husband and moved into the city I live in now, living a block away from me. Shortly after, her two sons (currently…
Read more Dear Penny: My Sister Is Broke Due to Her Freeloading Sons. Do I Help Her Anyway?Dear Penny, A few years ago, my parents got divorced. I’m in my mid-30s with my own family. The divorce was messy with lots of debate over money.…
Read more Dear Penny: My Dad Spends Up to $30K/Month. Could I Be Liable for His Debt?Dear Penny, My boyfriend of eight years stopped working four years ago. At the time, he told me it was because he needed to complete a remodel of…
Read more Dear Penny: How Do I Motivate My Boyfriend Who’s Refused to Work for 4 Years?Dear Penny, I had a handyman with two helpers do remodeling in my house over a period of many months. Sometimes, all three came to my house; sometimes,…
Read more Dear Penny: My Handyman Says I Should Tip Him $20/Job. Seriously?Dear Penny, I’ve earned more than the Social Security income limit for more than 35 years. I own my own business with my wife. She worked for 12…
Read more Dear Penny: Can I Pay My Wife So She Can Get Bigger Social Security Checks?Dear Penny, My grandfather worked hard his entire life and eventually became a fairly wealthy man. When he wrote his will, I was just a baby and my…
Read more Dear Penny: I’m Getting an Inheritance, but Grandpa Forgot About My SisterThe way people bank, invest and manage money has changed rapidly over the past few years and Cash App is one of few platforms that has been nimble…
Read more Scared of Trading Bitcoin? Cash App Isn’tDear Penny, We are a two-parent household with three children under 10. We make about $7,500 a month combined but still struggle and end up living paycheck to…
Read more Dear Penny: Should We Cut Out Kids’ Sports if We’re Always Broke?Dear Penny, My boyfriend of three years now has charged up $10,000 on my credit card until finally I put a stop to it. He started a business…
Read more Dear Penny: My Boyfriend’s Debt and Crypto Loss Cost Me $48K. Can I Trust Him?Dear Penny, I have a 32-year-old daughter who seems to think that it’s OK to not pay rent or be a contributing adult while living with me. I…
Read more Dear Penny: How Do I Kick Out My 32-Year-Old Daughter After 2 Years?Dear Penny, My husband’s parents have always expected their adult children to pay their way for restaurants and vacations, and whenever they need or want something that they…
Read more Dear Penny: Are We Jerks if We Don’t Pay $600 for My In-Laws’ Housecleaning?Dear Penny, I’ve decided to basically cut off my daughter once she’s finished high school, which will be just over five months from now. She didn’t do anything…
Read more Dear Penny: Should I Tell My Daughter She’s Cut Off at 18 Now or Wait?Dear Penny, My brother owes me over $6,000, and he is taking forever to pay it off. He owes money to banks as well. Would it be better…
Read more Dear Penny: My Brother Owes Me $6K. Should I Forgive the Debt or Sue Him?Dear Penny, I need some insight into today’s wedding protocol. My sister’s stepdaughter is getting married. I received a non-personalized notecard saying that the wedding is downsizing, and…
Read more Dear Penny: Do I Have to Send a Gift if I Was Uninvited From a Wedding?Dear Penny, I’m a single mother, and I’m trying to best plan how to protect my daughter if I were to pass. I have a life insurance policy,…
Read more Dear Penny: Can My Daughter Inherit Life Insurance if She’s Still a Minor?Dear Penny, My boyfriend’s mother passed away in April 2022. In 2000, she refinanced her deceased mother’s brownstone. She had her name and her two adult sons’ names…
Read more Dear Penny: I Refuse to Sign My Boyfriend’s $5,000/Month Mortgage. Am I Wrong?Dear Penny, My boyfriend is a bit of an underachiever. He’s 52 and makes $15 an hour working about 25 to 30 hours per week. He has his…
Read more Dear Penny: Is My Underachieving 52-Year-Old Boyfriend Using Me?Dear Penny, My 17-year-old grandson is working after school and putting half of his salary in a savings account. His grandfather and I have prepaid his college tuition,…
Read more Dear Penny: Can My 17-Year-Old Grandson Invest in a Roth IRA?Dear Penny, I have inherited $150,000 from my father. What can I do with the money so that my children’s father will not know about it ever? Also,…
Read more Dear Penny: Can I Keep My $150K Inheritance Secret From My Kids’ Dad?
