8 Super Awkward Money Situations… and How to Handle Them Like a Pro

Just talking about money is often uncomfortable, and then there are the really awkward situations involving money…

Many years ago, I was on a blind date in a restaurant at the top of a fancy hotel. When the bill arrived, I looked out the window at my car far below in the parking lot — and realized my wallet was in it.

Like a scene from a sitcom, I awkwardly ordered another dessert and excused myself to go to the bathroom, then ran down 13 flights of stairs (if I’d used the elevator, my date would have seen me).

Wallet in hand, I ran back across the parking lot, took the elevator to the 12th floor and walked up the last flight of steps, arriving at the table slightly sweaty and out of breath. Of course, I had to eat the extra dessert on a full stomach to complete my deception.

Hey, who hasn’t forgotten their wallet at least once, right?

Here are some other common — but awkward — money situations you may have faced, along with a few tips on what to do.

1. Your First Request for a Raise

It’s never easy to ask your boss for a raise, but the first time is the worst time.

I think I presented my first request something like this: “Do I get a raise or do you want to hire someone else?”

Although I was lucky enough to get the raise, that’s not the way to do it.

Preparation and catching the boss at the right time will make your request less awkward and more likely to succeed.

Mondays are often stressful for everyone, so wait until a calmer moment later in the week — ideally, just after you’ve completed some project.

For more strategies, see my post on how to get a raise.

2. Your Credit Card Is Declined

My credit card was declined in a gas station while there was a line of people behind me.

Filling up at gas stations 1,000 miles apart on the same day is apparently suspicious activity to a credit card company (it was a long trip). Fortunately, I resolved the problem with a phone call.

Even if you’ve done nothing wrong, you’ll probably have a credit card declined at some point, and it can be uncomfortable.

If you’re traveling long distances — and especially if you’re going to another country — call your credit card company to put a note on your account.

Another easy solution is to always carry more than one credit card.

If you’re smooth enough, you might run the second card like it’s the first, so everyone can think the card just didn’t read right the first time. Having some cash in your wallet is also a good idea, just in case.

3. You Forgot Your Wallet

If you’re lucky, it’s nearby — as in only 13 flights of steps below and across the parking lot.

But maybe you left your wallet at home, and you don’t realize this until… well, until you need it, of course. What do you do?

You can have your date pay, and promise to settle up as soon as you get your wallet.

Or you can recreate a scene from some romantic comedy, and call a friend from the bathroom to have him run over with your wallet or some cash.

If you’re out with a group of friends, you’ll have to hit up one of them for a loan.

One way to make it less awkward: Pay back the money you owe immediately with a PayPal or Venmo transfer using your phone. Your date’s impression of you might quickly change from “moocher” to “problem solver.”

4. You Don’t Know Who’s Paying

You’re on a date and the check comes.

You almost break each other’s fingers when you both reach for it. Or worse, you both just leave the check sitting there… and then your eyes meet.

Now that’s awkward.

Who should pay on a first date? Men pay 68% of the time, according to eHarmony.com — but that doesn’t really answer the question. It just shows gender-based expectations in our culture haven’t completely changed.

To avoid the awkwardness, assume you’ll pay if you proposed the date, but reach for the check even if you were the one asked out.

When your date says, “I’ve got it,” you can simply say thank you. In the worst case, you’ll pay for a lesson about the other person’s expectations.

5. Your First Money Talk With a Significant Other

When you move in with your girlfriend or boyfriend — or get engaged — the time will come for the money talk.

How will you handle bills? Will you split them? Will one person stay home and the other work? Do you need permission from your significant other before making large purchases? What about retirement planning?

Although there’s a lot of advice out there on how to talk to your spouse about money, it may still be awkward the first time. It’s probably best to just dive in and do it.

Couples who talk about money are less likely to divorce, reports MSN Money — and more likely to accumulate significant assets.

6. Splitting Expenses With Roommates

Maybe your roommates are honest and expect to pay their fair share, but they might not have the same ideas as you about how and when to pay.

You might prefer to send a check as soon as the electric bill arrives, while your roommate might be in the habit of paying bills in cash — and only when a late notice arrives.

So how do you handle money matters with roommates?

It’s best to clarify everything before you share an apartment or house. Put it in writing. You don’t need a formal contract, but if you can point to a piece of paper listing what was agreed to, it’ll be easier to resolve any money issues.

To avoid many problems with splitting bills, like arguments about who’s using more water or electricity, or who has the bigger room, consider avoiding the split altogether.

Rent or buy in your name and then charge roommates a set amount. See my guide on how to rent out rooms for more suggestions.

7. Asking Parents for Help

Life happens, and there may come a point where you need to ask your family to bail you out of a financial mess.

It becomes particularly awkward by the time you’re in your 30s.

To make it easier for everyone involved, have a solid plan in place before you ask mom and dad for money — or to live in their basement. You want them to know you made a mistake, but you already know what’s necessary to correct it.

In other words, tell them in writing exactly how you’ll repay them and when, and/or exactly how long you’ll need to stay with them — and how you’ll save the money to move out.

8. Collecting Debts

It’s never really comfortable to remind someone they owe you money, but it’s especially awkward with friends and family.

Fortunately, there are a few ways to make it easier to approach the subject.

First, if you have an irresponsible friend who’ll probably never pay you back, make a small loan before he needs it.

When your friend needs to borrow big money in the future, he’ll ask someone else because he still owes you money. I can tell you from experience that this cheap “shame” insurance policy works.

Another approach is to make it clear that loans are an investment, and you expect interest and collateral.

I’ve had a friend come to me a year late to repay a loan and reclaim his TV. I simply said, “Keep the money; I sold the TV a long time ago.” I make it clear loans are business to me, not a personal matter, so I’ve never lost a friend over a bad loan.

Also, I find an email about a late payment less uncomfortable than an in-person reminder.

You can find more suggestions in our previous post on what to do when family and friends want to borrow money.

Your Turn: Have you faced any of these awkward money situations? Tell us about your experiences.

Steve Gillman is the author of “101 Weird Ways to Make Money” and creator of EveryWayToMakeMoney.com. He’s been a repo-man, walking stick carver, search engine evaluator, house flipper, tram driver, process server, mock juror, and roulette croupier, but of more than 100 ways he has made money, writing is his favorite (so far).