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sad man at casino table

I lost big at the casino last week. If the IRS taxes gambling winnings, can I write off all my losses?

You walk into a casino hoping for a lucky night. But while you might know that the IRS wants its share when you win, the bigger question for most of us is: can we write it all off when we lose? The answer is more complicated than most gamblers realize.
June 18, 2026 Jesse Singer
Cash Advance

I keep taking cash advances to pay other cash advances. What’s the endgame here?

If you keep using cash advances to pay off other cash advances, you’re not alone, and you’re not broken, but you are stuck in one of the most expensive debt cycles out there. Let’s talk about what’s really happening and where this road usually leads.
January 21, 2026 Marlon Wright
average concerned woman face

My parents paid into the system for decades, but now they’re being denied benefits over paperwork. They need what they're owed, what can I do?

After decades of working and paying taxes, retirees expect the benefits they earned to be there when they need them. But small administrative mistakes can sometimes delay or even block access to those benefits. If your parents are facing a denial because of documentation issues, don't panic: There are still steps you can take to challenge the decision and protect what they are owed.
June 16, 2026 Carl Wyndham
Facebook  Internal

My wife secretly guaranteed a loan for her best friend and now collectors are calling. Can someone else's debt become our problem?

It often starts with a phone call that makes no sense. A collector asks for your spouse, mentions a loan you have never heard of, and suddenly your household feels exposed. If your wife secretly guaranteed a friend's debt, the big question is whether that obligation can spill into your finances too.
June 18, 2026 Carl Wyndham
man holding keys to safe, while another man stands beside the safe

My landlord says he needs a key to my in-home safe because it's "part of the unit." Can a landlord seriously ask that?

If your landlord asks for a key or code to your in-home safe because it is “part of the unit,” your gut reaction is probably the right one. In most situations, that request is far outside what landlords normally need to manage a rental. Landlords generally have rights to access the unit itself in limited circumstances, but that is very different from a demand to access a tenant’s locked personal container.
June 18, 2026 Miles Brucker

My boss told me to fake a family death so I could attend a conference in disguise. Am I complicit?

A compelling workplace-advice article exploring what to do when a boss demands unethical behavior—like faking a family death to attend a conference undercover. This engaging guide helps employees navigate toxic leadership, understand complicity, set boundaries, and protect their professional integrity with humor, insight, and practical strategies.
December 17, 2025 Jack Hawkins
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My pretty well-off sister wants me to help pay for our parents' nursing home because she "can't afford it." Do adult children have that obligation?

Your sister says she cannot afford Mom and Dad’s nursing home bill, so now she wants you to chip in. It feels personal, urgent, and maybe a little guilt-soaked. But before you write a check, it helps to know a key fact: in most cases, adult children are not automatically responsible for paying a parent’s nursing home bill.
June 17, 2026 Carl Wyndham
Facebook  Internal

My parents sold our cottage, but they gave all the money to my sister and told me it's because "she has children." Do I have any right to be upset?

Few family disputes sting like this one. Your parents sold the family cottage, turned the proceeds over to your sister, and explained it away with one painful reason: she has children and you do not. If that sounds unfair, you are not overreacting just because your feelings are hurt.
June 17, 2026 Carl Wyndham
woman-counting-the-money

How The Rule Of 114 Can Triple Your Investments

You’ve probably heard of the Rule of 72, the quick trick for estimating how long it takes money to double. The Rule of 114 is its less famous cousin. Instead of showing when your money might double, it helps estimate when it could triple.
June 17, 2026 J. Clarke
Caretaker looking concerned

I became my father’s caregiver, and now I’ve drained my own savings. Is there government support for people in my situation?

Most people don't become caregivers because they planned for it. One day you're helping your dad get to appointments, and before long you're managing medications, handling paperwork, driving him everywhere, and spending money you never expected to spend. If you've watched your own savings account shrink while caring for a parent, you're definitely not alone. The good news is that there may be government programs, tax breaks, and other forms of assistance that can help ease some of the financial pressure.
June 17, 2026 J. Clarke
Worried man in front of a house.

I inherited my mother’s house, but I can’t afford the maintenance and taxes. What are my best options?

Most people assume inheriting a home is always a blessing. In reality, many heirs discover that property taxes and maintenance costs can be a burden.
June 18, 2026 Sammy Tran