Taxpayer asks:

Reading about you connected me to this site. I had a small question.

That is can I double my deductions on my 2019 taxes being that last year I took the standard deduction. Such as House taxes, mortgage, charitable donations. 

Thank You

Taxgirl says:

I’m glad that you found the site!

Under the Taxpayer Cuts and Jobs Act (TCJA), more taxpayers are claiming the standard deduction. The changes typically benefit taxpayers who might have some itemized deductions (like home mortgage interest) but not so much that they exceed the new standard deduction amounts. The amounts are pretty generous with the standard deduction amount for married couples starting at $24,400 in 2019 (higher standard deductions may be available for those over age 65 and/or blind). You can find the numbers for 2019 here and for 2020 here.

If the numbers work out for you to claim the standard deduction in 2019, that doesn’t necessarily mean that it will work out the same for 2020. Circumstances change. And it’s absolutely the case that you can opt to claim the standard deduction in one year and itemized deductions in another. 

It sounds as though you are asking whether if you claim the standard deduction in one year – and therefore have unused itemized deductions in that year – you can simply roll those deductions into the next year. The answer is no. The rules regarding deductibility remain the same as always: you’re entitled to the deduction in the year the expense is paid. So, if you pay home mortgage interest in 2019, you can only claim that expense in 2019. If you claim the standard deduction for that year, then your deduction for home mortgage interest is “lost” (I used quotes here because you’re still benefiting from the higher standard deduction that year).

But this does lend itself to some planning ideas. If you expect that you might have higher expenses in one year – say, you have a significant medical procedure coming up in 2020 – you can adjust the timing of your other costs. So instead of writing that check to charity in 2019, consider doubling up in 2020. That’s called “bundling” – the idea that you can bundle expenses in one year to produce a higher itemized deduction total. It’s totally legitimate planning, but again, it only works if you pay the expenses in the year that you intend to claim the deduction.

Before you go: be sure to read my disclaimer. Remember, I’m a lawyer and we love disclaimers.
If you have a question, here’s how to Ask The Taxgirl.

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  1. my understanding is that you cannot deduct pre-paid medical expenses. So your plan to pay in advance for a procedure you plan to have the following year is not deductible.

    • Kelly Reply

      I would argue that you can, within limits, deduct pre-paid medical expenses. Pub 502 states (regarding Payments for future medical care), “Generally, you can’t include in medical expenses current payments for medical care (including medical insurance) to be provided substantially beyond the end of the year.” The word “substantially” has weight. But, it also says earlier, (at What Expenses Can You Include This Year?), “You can include only the medical and dental expenses you paid this year, but generally not payments for medical or dental care you will receive in a future year.” I find that contradictory.

      There is no such restriction in the statute which says:

      There shall be allowed as a deduction the expenses paid during the taxable year, not compensated for by insurance or otherwise, for medical care of the taxpayer, his spouse, or a dependent (as defined in section 152, determined without regard to subsections (b)(1), (b)(2), and (d)(1)(B) thereof), to the extent that such expenses exceed 10 percent of adjusted gross income.

      That notwithstanding, I wasn’t suggesting that you pre-pay medical expenses… I was suggesting that, if you knew you had a medical expense coming up, you bundle your other expenses to take advantage (in case you exceeded the standard deduction).

      EDITED TO NOTE that the two statements both appear in Pub 502 currently, just in different spots.

      • Kelly Reply

        UPDATE: After discussing this matter (Pub 502) with a few of my tax pro colleagues, we’ve asked the IRS to chime in. I’ll let you know what they say.

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