The Art Gallery of Calgary this spring filed a lawsuit against former president Valerie Cooper, seeking nearly $500,000 and alleging she’d improperly expensed massages, home repairs and clothing. Around the same time, Bev Oda, the federal minister for international co-operation, apologized for expensing a $16 orange juice, among other indulgences. Some expense claims are clearly misguided, many more fall into a worrisome grey zone. “Expenses aren’t something you want to ask forgiveness for later,” says Andrea Fraser, vice-president of human resources for DAC group. We asked Fraser and Fiorella Callocchia, the specialist lead of human capital consulting at Deloitte, to weigh in on some tricky situations. (Illustrations by Remi Geoffroi)

1. You only want a salad for dinner, but feel like having a couple of drinks. If it costs less than a regular meal, is it OK to expense extra alcohol?
The Experts: Fraser says she gets that request all the time, and has said yes, but it depends on your firm’s culture. “Lots of companies will not approve alcohol at any time,” says Callocchia. “It’s the risks of it. You decide you’re going to have a salad and five glasses of wine. You’re impaired; you slip on the way back to the hotel. Or you’re drunk at a meeting.”
The Bottom Line: Learn your company’s feelings about booze before you order that Pinot Grigio.
2. You stayed with relatives while on a business trip and saved the company on hotel costs. Can you expense a thank-you gift for your family?
The Experts: “If you saved the company money by staying with a relative, something like that should be forgivable,” says Fraser. Callocchia disagrees, however. “You’re dealing with a potential conflict of interest. You’re going to buy your family a gift. Who’s the greater beneficiary, the company or you? In this case, it’s you.”
The Bottom Line: Expense it, but tread lightly. Make the gift a modest one.
3. You got a parking ticket. Can you expense it?
The Experts: “I have not seen in my 30 years a company that would pay for a ticket,” says Callocchia. At most, a fine might be covered by whatever your company already allotted for mileage, says Fraser.
The Bottom Line: Unless a long meeting made the ticket unavoidable, this is a cost most employees will have to swallow.
4. An airline left your luggage sitting on the tarmac in the rain, and now your clothes are soaked. Can you expense a new suit for a business dinner?
The Experts: “Expense it but be reasonable,” advises Callocchia. “If it was a $100 outfit that got ruined, you can’t go out and buy Chanel.” And if the airline compensates you later, remember to reimburse your company for the expense payment. “You can’t double dip,” she says.
The Bottom Line: If clothing is damaged in the line of duty, the company should replace it. But it’s not an excuse to upgrade your wardrobe.

5. You’re vegetarian. Or keep kosher. Or are gluten intolerant. If the only appropriate restaurant is extra-expensive, is that OK?
The Experts: “I don’t know any company that would want you to eat things you can’t eat,” says Callocchia. “That’s not an unreasonable request, but you have to plan this out, talk to your manager.”
The Bottom Line: Expense your pricey food, but keep your boss in the loop about your diet.
6. You’re going on a business trip and don’t have anyone to watch your kids—or feed the cat. Can you expense babysitting or pet care?
The Experts: Probably not. “It’s just the cost of doing business,” shrugs Fraser. “If travelling is part of your job, you should find something to do with kitty.”
The Bottom Line: Unless the trip was a last-minute surprise, expect to shell out for any personal costs that come from being away from the nest.
7. You’re entertaining a client and they want to go to a casino. Can you expense some chips? What if they want to go to a strip club?
The Experts: “That’s where most companies would say no, offer alternatives,” says Callocchia—such as dinner or a show. She tells a horror story of a female employee at a Toronto pharmaceutical company who felt compelled to tag along when her male colleagues visited a strip club. “She said, ‘I was so uncomfortable, I actually felt demeaned and diminished as a woman, but I didn’t feel I could speak up.’”
The Bottom Line: Just say no.
8. You’re relaxing in your hotel room and really want a chocolate bar. Can you expense snacks? Is it OK to take them from the mini-bar?
The Experts: “If you’re travelling, you want to maintain your normal standard of living,” says Fraser. “If you have a glass of wine every night, you should be able to have a glass of wine.” Most companies wouldn’t approve of mini-bar prices, however.
The Bottom Line: Sure, snacks are fine. Just use common sense.