Is your ex costing you a tax deduction?

Fifty percent. That’s the whole number, and no amount of “but this client signs the checks” is going to move it. Congress set the ceiling, the IRS enforces it with a straight face, and your negotiating skills — however excellent at the actual lunch table — do not extend to the tax code, which has never once been swayed by a good sales pitch.

The rule: you can deduct 50% of the cost of a business meal as long as it’s not lavish or extravagant, you (or an employee) are actually present, and the meal has a real business purpose — closing a deal, keeping a relationship warm, talking shop. A solo dinner where you privately reflect on your business does not count, no matter how many notes you took on a napkin. A lunch where you actually talk to an actual client does.

What counts as “the meal”: food and drinks. That’s it. If lunch turns into 18 holes of client golf, the golf is 0% deductible — entertainment lost its deduction entirely in 2018 and the IRS has shown no interest in bringing it back. If you’re at a ballgame or a concert, get a separate receipt for the food, or the whole outing gets lumped in with the entertainment and disappears from your return entirely.

What you need to keep: the amount, the date and place, who was there, and why. “Lunch w/ client” scrawled on a receipt six months after the fact is not documentation. It’s a vibe, and the IRS does not accept vibes.

The exceptions that hit 100%: company-wide holiday parties, meals handed out to the general public as marketing, and meals baked into an employee’s W-2 wages, among other exceptions.

Keep taking the clients to lunch. Just keep the receipts, and keep your expectations at exactly half.

👉 Review the full rules on business meal deductions

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Only when you sell. Or trade it. Or spend it. Shuffling it from one wallet you own to another wallet you also own does nothing to your tax bill, because as far as the IRS is concerned, you haven’t done anything — you still own the same asset, it’s just sitting in a fancier drawer now.

The trigger is a taxable event, not a transaction. The IRS taxes you when property changes hands or changes form: sold for dollars, traded for a different coin, or spent on something real. Moving Bitcoin from Coinbase to a hardware wallet you control checks none of those boxes. You didn’t sell, trade, or spend anything — you just relocated it, the way moving cash from one pocket to the other doesn’t generate a 1099.

What does trigger tax: cashing out, swapping one coin for another, and paying for goods or services with crypto. Each of those counts as selling property, which means calculating a gain or loss based on what you paid versus what it was worth the moment you let go of it.

Since you mentioned it’s up significantly: congratulations, and also, how long you’ve held it now matters a great deal. Past a year, you’re in long-term capital gains territory: 0%, 15%, or 20%, depending on income. Under a year, it’s taxed as ordinary income, which is the tax code’s way of telling you patience is a virtue and impatience is a bracket.

One thing that trips people up: transfer fees. Network fees for moving crypto between wallets are often paid in crypto itself, and technically that tiny sliver counts as a disposal. In practice, the amounts are usually too small to matter, but keep records of your basis anyway.

Move it, hold it, spread it across five wallets like a squirrel with trust issues. None of those is a tax event. The tax event is the day you actually cash out.

👉 See how the IRS treats digital asset transactions 

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If you own a business (or you’re building one), this one’s for you.

No. Child support is tax-neutral on both ends — you don’t deduct it, your ex doesn’t report it as income, and it doesn’t show up anywhere on either return. It’s rare that an IRS rule is this straightforward, so enjoy it.

The logic: the IRS treats child support as money spent on your kid, not income handed to your ex. It doesn’t tax you for feeding, housing, or clothing your own child under one roof, and it doesn’t start taxing you for it just because that roof split in two.

This is different from alimony, which gets lumped in more often than it should. Alimony from agreements finalized before 2019 was deductible to the payer and taxable to the recipient. Agreements from 2019 on lost that treatment entirely — it’s now considered nondeductible and nontaxable, same as child support.

What can still move the needle: the Child Tax Credit and other dependency benefits go to whichever parent claims the child, which is usually — not always — the custodial parent. That’s a separate question from who’s writing the support checks, and it’s worth nailing down clearly in the custody agreement, since it’s the one spot where the tax code actually cares who’s supporting whom on paper.

Paying child support was never going to get you a deduction. It’s also not costing you a cent beyond the check itself.

👉 Read the IRS rules on divorced or separated parents

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