Eight awkward money moments and how to handle them

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People will overshare about pretty much anything these days — from bodily functions to intimate discussions they’re having with their therapist. Broaching topics like that can definitely push some social boundaries, but I still think the most awkward moments stem from money.

Whether it’s an invasive question or a request for a loan, it can be really hard to know what to do or how to react. Which is why I’ve listed eight major awkward money moments along with a few suggestions about how to handle them as graciously and honestly as possible.

How much do you make?
You’re out for drinks with your good friend from work. She’s complaining about her performance review and thinks she deserves a raise. She turns to you and asks, point blank, “How much do you earn?” She’s a good friend and has helped you out in the past — what do you do?

The best approach is not to answer the question. Talking about how much you make with a co-worker is a dangerous game, no matter how close you are. In fact, some companies have a policy that prohibits any discussion of salaries among staff. Just tell her you’re not comfortable sharing that information — and ask her if she knows what other people in her position make at competing firms. It’s information she should have — you should always know how much your job is worth in the marketplace.

An invitation to the dreaded birthday dinner
Last year your friend held her birthday dinner at the most expensive restaurant in town — you ended up shelling out $150 and all you ate was a salad and a glass of soda water, while everyone else had steak and champagne. This year she wants to go to another expensive place and you just can’t afford to do it again. What do you do?

You are fully within your rights to beg off and to make a date to celebrate her birthday at another time. Offer to make her dinner at your place at a later date — cook a special meal and book some time to catch up on your own.

That being said, the person organizing the meal should make sure that everyone knows who’s paying for what ahead of time — and s/he should handle the cheque when it comes, making sure it’s divvied up fairly.

What did your house cost?
Some people talk about money all the time, from how much their fancy car costs to the price of their designer handbag. Sometimes it can be fun to swap stories about how much things cost ("I can’t believe I got these shoes for $29!") — but there are situations where it’s just plain awkward. "How much did you pay for your house?" is one of them.

I think it’s best to avoid answering this question unless you are really comfortable with the person you’re chatting to. There are plenty of ways to sidestep the question without being rude — “Too much in this market,” is probably what most of us would be willing to admit. And if they persist and keep asking, just politely decline by saying that you don’t feel comfortable sharing that information. There are plenty of other things to talk about anyway.

Who picks up the cheque?
You’re out for lunch with work colleagues — the bill comes and no one’s jumping for it. Who pays?

In my view, it depends on a couple of things. If you’re with a superior and they’ve invited you to talk work stuff, chances are s/he will reach for the bill. But if it’s work related and you made the invitation, assume you’ll be footing the bill.

Lunch with a bad tipper
You’re out with a friend and you’ve enjoyed great service at the restaurant. You decide to split the bill and you notice your friend is leaving a really bad tip. Should you leave extra to make up for it or just say something?

This can be a tricky situation. You can feel her out by complementing the service and letting her know you’ll be leaving a really good tip. She might rethink her tip or tell you should thought the service was terrible. Either way, if you can, just add a buck or two to your bill to compensate and rethink splitting the bill with her again!

Your friend borrowed money and hasn’t paid you back
You lent your friend $500 to help her out when she was between jobs. She’s working again and earning a great salary. You’re happy for her, but she hasn’t mentioned the loan since and she hasn’t paid you any money back. What do you do?

Be honest. After all, you did something really nice in lending the money. Paying it back promptly (albeit when she can) is a sign your friend respects you and appreciates what you did to help. Explain that you would like to talk about the money and when you might expect to get it back — tell her when you need it and make arrangements to figure out the best way to repay it.

If a friend or family does ask you for a loan, you need to think carefully about whether or not you can afford it — I firmly believe that if you can’t afford to lose the money, then don’t loan it.

I’m walking/riding/running/canoeing 10 K — please give me money!
These days it’s easy to feel overwhelmed by requests from friends and coworkers involved in charity events and fundraisers — and while their aim is a noble one, it’s really hard to cough up money for every single cause. Besides, a lot of us have our own charities that rely on our donations. Do you just ignore the sponsorship requests or do you just give in and give 20 bucks?

There are a few approaches you could use — one of them is to ignore the request, especially if it comes from someone you don’t know all that well and it’s obviously being sent to a mass email list. But if it’s a close friend and you just don’t have the money to support the cause, then just politely say you don’t have the cash. You could even offer to pitch in and support your friend some other way (handing her water along the marathon route?).

Hanging out with rich friends
You’re saving your pennies and your good friend is earning the big bucks — she always wants to check out the most expensive restaurants in the city, complete with lots of wine. Do you have to keep up to stay friends?

The answer is no — there are plenty of things you can do with friends that don’t cost a fortune. In fact, the best nights can be those spent at home, with a nice home-cooked meal to share and a tasty (and cheap) bottle of wine on the go. Be honest with your friend and tell her you can’t afford to eat out — if she’s a true friend her priority will be you, not the fancy restaurant.

Caroline Cakebread is a Toronto-based financial writer and editor. She’s also a recovering academic and the mother of two kids. Check out her personal finance blog for Chatelaine Your Money.