“I Do” = “You Owe”? 💍

Roses are red,
Violets are blue,
The IRS loves your money
More than you do.

Forget chocolates and flowers. Nothing says “commitment” quite like joint and several liability. This Valentine’s Day, we’re exploring the romantic side of the tax code, from the “marriage penalty” to the joys of alimony deductions. Grab a glass of wine (it’s not deductible, sorry) and let’s talk about love and audits.

This week’s lineup:

Filing 101

💍 Saying “I Do” to the IRS

You said ‘I do,’ popped the champagne, and danced awkwardly but joyfully. The honeymoon awaits. But lurking in the background, ready to crash your newlywed bliss with a stack of paperwork, is … the IRS.

Nobody at the wedding toasts to the bureaucratic avalanche that comes with marriage. But here we are. Because love may be eternal, but your marital status on Dec. 31 determines your entire year’s tax situation.

The Dec. 31 Rule (The IRS is Very Literal)

This is the most straightforward rule in the entire tax code. For tax purposes, your marital status for the whole year is whatever your status was on the very last day of that year.

The IRS doesn’t do “it’s complicated.” You’re either in the club or you’re out, and that one day decides everything.

The Newlywed To-Do List (Sorry, More Paperwork)

Before you can even think about filing your first joint return, there are a few housekeeping items.

Joint vs. Separate Filing (The Great Debate)

For the vast majority of couples, filing jointly is the way to go. It’s almost always more financially beneficial, offering a larger standard deduction and more access to tax credits.

But here’s the catch: filing jointly means you have “joint and several liability.” This is a fancy legal term meaning the IRS can come after either of you for the entire tax bill, even if it was all your spouse’s fault. If your new spouse owes back taxes or student loans, your joint refund can be seized to pay their old debt.

So when might filing separately make sense? If one spouse has massive medical bills, the lower income threshold might make them easier to deduct. More commonly, you might file separately if you have serious concerns about your spouse’s tax situation and want to keep your finances legally separate.

Are you looking at a tax penalty or a tax bonus? The math changes based on your combined income. Read on to see where you land and how to file for “Innocent Spouse Relief” if things go wrong. Keep reading →

Business & Gigs

🏖️ Retiring Solo: The 1099 Guide

Ah, the 1099 life. Freedom. The flexibility. You’re your own boss, your own scheduler, your own everything. You glide through life like a lone wolf, until … you remember you’re also your own HR department, payroll manager, and (horrifyingly) benefits coordinator.

This is the quiet terror of the gig economy. Nobody hands you a 401(k). There’s no pension. No employer match. Just you, your stack of 1099-NECs, and the sinking realization that you owe the entire 15.3 percent self-employment tax all by yourself.

Welcome to the gig worker’s retirement crisis.

It’s not that gig workers don’t want to save. It’s that the entire system was built for the 9-to-5 world you left behind. When you’re paid per project, every dollar feels like rent money, taco money, emergency money. Almost never “retirement-in-2055” money.

But the tax code actually gives you some solid tools. You just have to use them.

Your Retirement Arsenal

1. IRA (Traditional or Roth)

Your baseline. For 2025, you can put in $7,000 (plus a $1,000 catch-up if 50+). It’s a start, but it won’t carry your whole retirement alone.

2. SEP IRA (The Big Gun)

Perfect after a strong year. Contribute up to 25 percent of net self-employment income, capped at $70,000 for 2025. This one can slash your taxable income fast.

3. Solo 401(k) (The Power Tool)

The most flexible option for a solo business. You act as both “employee” and “employer.”

You often reach the max with less income than a SEP, which is why tax pros love it.

You’ve heard of the retirement crisis, but have you heard of the government’s new solution? We’re breaking down the “GSS Credit,” a new law that finally gives freelancers a “company match” of up to $1,500. Keep reading →

Money Moves

💔 Taxes and Divorce: What the IRS Really Wants

Divorce is tough enough without the IRS stepping in. But if you don’t plan for tax issues while everything is being sorted out, you can end up with expensive surprises.

1. Your Filing Status Depends on Dec. 31

If you’re legally married on Dec. 31, you’re considered married for that whole year.

Your filing options:

2. Head of Household May Save You

You may qualify if:

Better rates, bigger deductions.

3. Alimony and Child Support

Divorces finalized before 2019 follow old rules.

4. Who Claims the Kids?

The custodial parent gets the credits unless they sign Form 8332 to transfer them.
No form = automatic rejection.

5. Protect Yourself After Filing

The IRS is the third party in every divorce. Plan your taxes before the ink dries. It’s cheaper than fixing a mistake later.

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Wild Tax Tales

⚖️ Marriage, Taxes, and Forgery

We usually think of a signature as the final word. It is the thing that makes a contract binding. But when it comes to the IRS and marriage, that ink on the page matters less than you think. You can actually be forced to pay taxes on a return you never signed.

It sounds crazy. But it happened to Ursula Haber.

Burton and Ursula Haber were having some marital issues. When tax season rolled around, Ursula refused to sign their joint Form 1040. Maybe she was protesting the marriage. Maybe she was protesting the taxes. We don’t know.

Burton decided to get creative. He signed his name. Then he signed Ursula’s name right underneath it. He told his accountant she gave him permission. Spoiler alert: she definitely did not.

Eventually, the IRS audited the return. They found a deficiency and sent a bill to both Mr. and Mrs. Haber. Ursula immediately fought back. Her argument was simple and seemed foolproof. She basically said, “I didn’t sign that. That is not my signature. Therefore, I am not responsible for that debt.”

The Tax Court didn’t buy it. They ruled against her using a concept called “tacit consent.”

Here is how the court saw it. Ursula didn’t sign the joint return. However, she also didn’t file a separate tax return for herself. On top of that, her income was included in the joint return Burton filed. The court decided that her actions showed she intended to file jointly to get the tax benefits. She only complained about the signature when the bill arrived.

Because she acted like a joint filer, the law treated her like one.

This brings us to the scary reality of “joint and several liability.” When you file jointly, you are 100 percent responsible for the tax bill. The IRS does not care who earned the money. They do not care who forgot to pay. They can come after either spouse for the entire amount.

The Haber case is a warning. Silence can be viewed as consent. If you are in the middle of a divorce or a separation, you need to be proactive. Do not just refuse to sign a joint return and think you are safe. You need to file a separate return. You need to create a paper trail that shows you are severing your tax life from your spouse.

If you don’t, the IRS might decide you agreed to the joint return anyway. And they will expect you to pay up.

The quick (and slightly prickly) stories we didn’t have time to get to:

If you made it this far, you’re our kind of nerd. Hit reply and tell us which story you want us to dive deeper into next week.