Awkward Money Moments and How to Handle Them

When I lived in New York City, the land of sky high real estate prices, the majority of small talk was about how much we paid for rent. You’d be amazed at the conversational acrobatics that could make a chat about the weather leap and twirl into the details of one’s rental agreement.

But outside of New York, when I asked, “How much do you pay?” while ogling someone’s built-in bookshelves, conversations ground to an awkward halt. Why? Because, nosey New Yorkers aside, talking about money is often taboo. And because we don’t talk about it, we can often find ourselves in awkward money situations with no obvious way out. If we adopt some openness around discussing money and temper it with some foresight and tact, we’ll be able to get out of many awkward money situations with grace. Here are four scenarios and how to handle them.

Your friend forgot his wallet at dinner. You spot him $30, but he forgets to pay you back. The great thing about technology these days: even if your friend forgot his wallet, he can immediately pay you back using an app like ChimpChange. As you pay for the meal, simply say, “I’ll spot you and you can pay me back from your phone now.”

Your friend should do it right then, but if he somehow also forgot his phone, you can remind him later. Send him two friendly reminders, but let it go after that. As a general rule, when you lend money to friends, be prepared to never see it come back to you. If that’s something you can’t afford, then don’t give the loan in the first place.

You go out with a group of friends. They order significantly more and want to split the check evenly. We’ve all been on both sides of this equation. It’s a delicate balancing act, wanting to pay your fair share while also wanting to make the bill paying process as seamless as possible.

Before you go with any group, assess the culture of the group. Some groups itemize their payments, others split the check evenly and don’t think twice about it. When I go out with my writer friends, we typically pay for the items we consumed. When I go out with my doctor and business friends, we typically split the bill evenly. So before you go out, ask yourself, does this group tend to split the bill evenly? And can I afford that?

It’s safe to expect most groups to split the check evenly. If you can’t afford that, arrange ahead of time to get a separate check from the waiter. You can also mention it casually to the host or the group that you’ll be paying separately, so it’s not a surprise at the end of the meal.

Your credit card gets declined. Have you ever been out of town or making a big, out of the ordinary purchase with a credit card and it was declined, but you know you hadn’t reached your limit? Next time, call your credit card company in advance so they don’t flag the purchase as fraudulent. This simple heads up will allow your purchases to go through without any hiccups.

However, if your card has been declined because you’ve gone over your limit, then let this be a wake up call to keep better track of your monthly spending. When this happens, don’t make a big deal of it in the moment. You will only make matters more awkward if you get angry or insist that the cashier has done something wrong. Simply apologize, retrieve your card and pay another way. When you get home, spend some time looking at your purchase history and see what you can change next month to prevent this from happening again.

Not having cash on hand when you need to tip. As our society becomes more cashless, it’s typical for people who work for tips to get short changed. The best way to prevent yourself from making this mistake is to always have a little cash on hand or, if you know you’ll be attending something where a service person should be tipped, come prepared. Of course, not all of us are boy scouts, and there will be times when we come up short. That’s no excuse to not tip. If you find yourself in this situation, find an ATM and return to give the tip to the person who served you. They’ll be very grateful to know that you remembered them and made the special trip to give them the tip they deserve.

No matter what sticky money scenario you find yourself in, a little thinking ahead can help you anticipate and avoid awkwardness. And if you still find yourself short changed, these tips can help you navigate each situation with grace.


The materials on this blog are provided for informational purposes only and do not reflect the opinions of ChimpChange LLC or Central Bank of Kansas City, Member FDIC. Several of these blog posts may contain links to content on third party websites which are provided for your convenience, please note that linked sites may have a privacy and security policy different from our own, and we cannot attest to the accuracy of information. ChimpChange LLC and Central Bank of Kansas City do not guarantee nor expressly endorse any particular product, service or third party content.