Canada’s most embarrassing tax questions, answered.

November 26, 2018

Taxes can get personal. Really personal. Especially if you don’t often share the personal details of your life with others. When it comes to taxes, the more your tax professional knows about your life the better, as it can lead to claiming tax credits you didn’t even know about.

Worried your complicated relationship status will cause your tax professional to snicker– even after you explained that you and Rachel were, in fact, on a break? Or too shy to ask whether your bikini wax warrants any tax breaks? Anyone who works in the tax industry knows that embarrassing questions surface all the time, and they go immediately into the vault with absolutely no judgement.

To help address any burning questions you might be harboring, we’ve shared some anonymous questions that H&R Block Tax Experts have been asked, and their surprising answers.

Q: I suffer from Inflammatory Bowel Disease and was told by my doctor to take IMODIUM®. Can I claim this expense on my taxes?

A: Sorry to hear about the IBS. We’re even more sorry to tell you that no, you can’t claim over-the-counter medication, even if it was recommended by a doctor. However, prescription medications can be claimed, so consider speaking to your doctor about options and hang on to those receipts.

Q: I'm a model and am encouraged by my agents to get monthly spray tans and bikini waxes. Can I claim this?

A: We get it, beauty can come with some upkeep. The good news is, if your employer requires you to pay for the cost of a spray tan or bikini wax as a condition of your job, then you can claim those expenses. As well, any items required specifically for a photo shoot are tax deductible, such as eyelash extensions. But before you start spending, you need to complete a signed Declaration of Conditions of Employment (T2200) indicating you are required to pay these expenses.

Q: My boyfriend's six-year-old son and the child’s half-sister moved into our apartment. Can I claim the Canada Child Benefit (CCB) for them, even though I’m not related to either child or married?

A: Diverse and blended family situations are the new norm. Related or not, if you and your boyfriend are common-law and have primary care and responsibility or shared custody of the children, you can apply to receive the CCB by completing the Canada Child Benefits Application form (RC66). But keep in mind that only one of you can claim it on your return.

Q: I own an adult film production company. Can I claim condoms as a business expense?

A: The CRA indicates items are tax-deductible (including the GST/HST paid on that purchase) as a business expense if it’s a reasonable cost for you to earn income. So, even condoms could be tax deductible (yes, you heard us right!) as it’s a necessary expense for your production company. In fact, if you are self-employed, there is a range of business expenses the CRA allows you to deduct, including:

  • Meals and entertainment – money spent on things like business lunches and coffee meetings are 50% deductible.
  • Business operating expenses – costs that are required for you to run your business, like office supplies, phone, and utilities.
  • Home office expenses – if your home is your principal place of business, you can claim a reasonable portion of your home expenses (such as rent or mortgage interest, home insurance, maintenance and utilities) based on the square footage of your office space and the amount of time you use it for business purposes.
  • Travel expenses – don’t forget to include any travel you may do for work, including attending conventions and business meetings.

You can find more on our Small Business Tax Checklist.

Q: I’m a stripper and need to fill my closet with stage clothing. Can I claim this as an expense given I’m wearing it solely for work?

A: Generally speaking, clothing isn’t normally considered a business expense, so designer pants picked up for an office job can’t be claimed. However, performers may be able to claim costumes used exclusively for work, so in this case, you may be able to claim your clothing. However, you will need to complete a signed Declaration of Conditions of Employment (T2200) indicating you were required to buy those clothes for your job. Overall, anytime your employer is asking you to pay certain expenses in order to keep your job, make sure they fill out that T2200 so you can get some money back in your pocket.

As the largest tax preparation firm in Canada, H&R Block has Tax Experts that can help guide Canadians through all types of situations at home and at work to ensure they’re getting what’s theirs when it comes time to file.

Canadians are encouraged to take time to understand how they can take full advantage of the credits and deductions available to them. For more information, visit one of H&R Block’s offices or online at

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