Think a tax question is too embarassing to ask? Think again

Awkward tax questions people have actually asked

Here are nine crazy tax questions to learn from



When it comes to taxes, everyone’s situation is personal. And some more personal than others. “People come into my office at tax time and often have a lot of questions about what they can claim,” says Valorie Elgar, senior tax professional with H&R Block. “Everyone wants to get the most out of their money.”

Elgar is the first to admit that a lot of these burning questions are often slightly embarrassing. Still, “better to bring it in and ask then not to ask and forego a possible tax credit or deduction,” says Elgar. “You never know—we may say ‘yes, you can claim that’ and that’s free money in your pocket.”

And Elgar knows exactly who’s most likely to ask these sensitive questions. “Millennials,” says Elgar. “People who are relatively new to doing their taxes are the ones who ask the most questions. Millennials, as well as the self-employed.”

Here are some discomfiting questions Elgar and other H&R Block tax preparers have been asked along with guidance on whether these items are deductible, or will earn you a tax credit:

Q: “I’m a stripper and I purchase clothing to take off on stage. Can I claim the full expense in the year purchased?”

A: “Normally, clothing cannot be claimed as a business expense. However, in the case of a costume you use exclusively for business purposes, you are able to claim an amortized portion of the purchase price each year.”

Q: “My wife is due with our first child. Can the baby’s diapers be considered a tax deduction since the child will need to wear them at all times?”

A: Unfortunately, baby diapers are a personal expense and cannot be claimed. Sorry!

Q: “After getting divorced, I moved in with another man. Later, the relationship ended—all within the same year. Help! What should my marital status be?”

A: Your most recent relationship had not lasted long enough at the end of the year for you to be considered common-law. That means your marital status is still “divorced.”

Q: “Can I deduct legal fees defending myself from charges of operating a grow operation?”

A: Legal expenses to defend yourself from criminal charges like the one you mentioned are usually not deductible. However, they could probably be deducted against business income from the grow-op.

Q: “I use a pet tiger in my act—his name is Bob. How do I claim Bob on my tax return?”

A: A living creature like Bob cannot be claimed. However, the expenses of feeding, accommodations for the tiger, security required for and by the tiger and medical care for the tiger are considered expenses and can be claimed.

Q: “As a woman, can I claim all of my feminine hygiene products on my tax returns as a medical deduction? This isn’t something I necessarily  want to spend my money on each month, but need to.”

A: Sorry, feminine hygiene products are considered a personal expense and cannot be claimed on your tax return.

Q: “I recently got married and my husband is in jail. Yikes—how does that affect my taxes?” 

A: As long as you are not separated by reason of a breakdown in your relationship, your marital status will not change. However, since you are not supporting him while he is in jail, you would not be able to claim him as a dependant. Your husband will also cease to be eligible for federal and provincial benefits (such as the GST/HST Credit and Ontario Trillium Benefit.)

Q: “I’m an Uber driver and have kept all receipts from purchasing snacks from 7-Eleven on my driving days. Can I deduct these as a cost of doing business?”

A: If you bought snacks to feed yourself, no. But if you bought some bottles of water and perhaps granola snacks and kept them in your car for passengers, then you can deduct this.

Q: “I just had a tummy tuck. Can I claim my cosmetic surgery bills as a medical expense?”

A: No, even if you really feel you need that tummy tuck, you’re not eligible to deduct it. And of course, even allowable medical expenses (such as braces or dental crowns) can only take your tax liability to zero.

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