10 Money Moments That Are Awkward for Everyone


Most of us don't like to talk about money, because when we talk about money, things get awkward. But it's not just the talking part that ruffles our feathers. Sometimes just being in a situation that relies on money can make us uncomfortable. From the first time you ask your boss for a raise to not having enough cash when tipping is suggested, these are the most awkward money moments in life.

1. The First Time You Ask Your Boss For a Raise

It's not easy asking your boss for anything, let alone a higher salary. In fact, I suspect that many people never speak up where money is concerned because they're afraid the boss will take it the wrong way or it might somehow affect their current employment status. I can assure you, however, that you cannot be penalized or fired for asking for a raise — because that would be illegal. There's a chance your boss could say no, of course, but that shouldn't stop you from standing up for yourself. If you think you deserve a raise or haven't received one in a while, don't be intimidated. Schedule a meeting to discuss your performance and take it from there. If nothing comes of it, at least you'll know where you need to improve. If it works out in your favor, on the other hand, well... you're welcome.

2. Deciding Who Pays the Check on a First Date

I have a real problem when someone on a date automatically assumes that the other person is paying. I don't want to be sexist, but this happens more among females than it does males when they're out together. I also see this imbalance when one person is younger than the other (at least in my personal experience); the oldest among the two is often expected to pick up the tab. But I don't mess with either of those scenarios. Instead, I have a solid solution to keep things fair. If I ask you on a date, I'll happily pay. If you ask me on a date, you should pay. And if we've decided mutually to go on a date, we should split the tab. No free rides from this show pony.

3. Forgetting Your Wallet When on a Date or Out With Friends

I think we've all forgotten our wallets at home on a date or while we're out with friends at least once, and it's a bit embarrassing. Especially if you have friends like mine who like to rag on you when you do something silly. It's a little worse on a date, though — even if your date is easy-going about the situation — because you want to make a great first impression. But these days the problem is easily solvable by being able to pay your portion immediately to the person who covered for you via PayPal, Venmo, or another mobile banking tool.

4. When Your Credit and Debit Cards Are Declined at Checkout

This has happened to me more than a few times, not because I didn't have the funds, but because my bank flagged unusual spending habits on my card when I'm on vacation or in an area that's not within my typical range. To avoid this particular problem when traveling, give your credit card company a call to let them know in advance where you will be. If however, you've been declined because you have gone over your limit, it's simply a strong reminder to keep track of your finances and not to take your credit for granted in the future. Do not act indignant and insist there must be something wrong with their machine.

5. Discussing Finances With a Soon-to-Be Spouse

Having the money discussion with the person you're about to marry isn't the most fun you'll have with each other, but it's a completely necessary conversation. Before your lives become intertwined with a binding legal contract, you both need to be honest about assets, debts, loans, savings goals, and anything else money-related. If you love each other, your past financial history shouldn't matter too much — unless someone's been hiding a huge secret — but it's a smart start to lay everything out on the table. (See also: 3 Simple Ways to Split Bills With Your Spouse)

6. Dealing With a Roommate Who Owes Rent

I have two ways of going about this. First, if you're not the landlord, your roommate's lack of payment shouldn't be your problem. This is why I recommend that everyone have separate leases. Without an individual lease for yourself only, you run the risk of having to cover for your roommate financially or deal with the consequences of their failure to pay — and that could mean eviction.

Secondly, if you own the property, you shouldn't feel awkward at all about asking your tenant to pay on time each month. Paying the bills on time is a fundamental adult skill, and, frankly, if they can't afford to live in your property, they should find another suitable option that's more in line with their budget.

7. Reminding Someone You've Loaned Money to That They're Late

I generally don't advise anybody to loan money to family or friends in order to avoid this awkward conversation altogether. But, if you somehow get suckered into loaning people cash, at least draw up a written contract to help avoid potential default. Establishing terms, like due dates and interest, will improve your chances of receiving your money on time.

8. Asking Your Parents to Help With Bills as an Adult

Quite honestly, the last people I want to ask for money are my parents. Somehow it feels as if I've failed if I'm running to Mom and Dad for cash, so I'd rather reach out to friends first. But if they're a last resort, don't just show up asking for a handout. Promise to pay them back — even offer to draw up the loan contract for them so they can respect your seriousness about the situation — and stick to your plan. While you're at it, take this time to figure out what's wrong with your financial situation that you needed to ask your parents for money, and try to address that simultaneously.

9. Explaining Overdraft Fees to Your Significant Other

Yep, even I've overdrafted before, and I hate when my bank sends me a note in the mail reminding me of the fact. Like I didn't notice it in my online banking statement. Oh, I noticed. And we all know what the little mailer looks like, so it's not like my husband has to open it to recognize that I've overdrafted. Then I have to tell him that I forgot about an automatic bill payment while I was Christmas shopping. Which will totally make me roll my eyes because it's my bank account and my error, but it's still awkward nonetheless.

10. Not Having Cash on Hand When Tipping Is Suggested

If you know you're going someplace where tipping is suggested, you should have cash on you. There are times, however, that you go someplace where you didn't expect to tip and you don't have any cash on you — and I'm not sure if there's anything more awkward than staring that service provider in the face, like, "my bad," before they sulk away cursing your name under their breath. In this case, go get the tip money you owe that person and give it to them after the fact. It'll totally make their day that you recognized your mistake, and it'll help you feel like less of a jerk for stiffing the poor guy or girl in the first place.

Are there other awkward money moments in life that you'd like to share? Let me know in the comments below.

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