Join our mailing list to find out more ways to make and save money with little time and effort.

15 Embarrassing Money Situations (And What to Do About Them)

Disclosure: Some of these links may be affiliate links and we may receive compensation when you sign-up for offers.


Apparently filling up at two gas stations 900 miles apart in the same day is considered “suspicious activity” by credit card companies. That’s what I discovered when my card was declined during a long road trip. Fortunately a phone call resolved the matter.

Who hasn’t had a credit card declined at least once? For that matter who hasn’t faced a variety of other awkward moments involving money? Years ago, on a first date, I forgot to tip the waitress (seriously, I just totally forgot), which was pointed out by my date after we left the restaurant. I ran back to leave a tip.

You too have probably faced some of the following awkward and embarrassing money situations. But if any of them happen again, or for the first time, with the suggestions here you’ll be prepared.

1. You Credit Card Is Declined

It usually happens with a line of customers behind you, but why? Bankrate says these are the most common reasons for a credit card being declined:

  • You make an unexpected international purchase
  • Your activity triggers fraud protection (gas stations 900 miles apart)
  • Your credit  limit has been reached
  • The information you enter doesn’t match your records
  • You’re late on a payment
  • Your credit score dropped too far
  • Your card has expired
  • A hold on the card puts you over the limit

If you have another credit card, you can quickly pull it out and complete the transaction. You can also pay cash. But both of those solutions assume some prior preparation, and that is exactly what you need to do to prevent a declined card or keep it from becoming a big issue. Try these steps:

  • Notify the credit card company when you leave the country
  • Carry a second card at all times
  • Carry some cash at all times
  • Put card renewal dates on your planner
  • Pay the bills on time
  • Monitor your credit
  • Double check the information you enter for a purchase
  • Remember that gas station and car rental holds count toward your limit

Unless you have a friend there to bail you out, it’s what you do before the incident that keeps it from being a big deal.

2. Asking for Your First Raise

The first time I asked a for a raise I threatened to quit if I didn’t get it. Awkward — and usually not the best strategy. So what can you do to make your first request for a raise less uncomfortable? Try these steps:

  • Be worth it
  • Show your worth
  • Be prepared
  • Ask at the right time

You’re doing a good job or you wouldn’t be asking for a raise, right? But your boss may not know your value, so be sure she learns. If you drop hints be casual rather than boastful. Example: “I just finished that project and it went better than planned, but I was wondering…” (insert any reasonable question here).

Prepare a “sales pitch” for why you deserve a raise, and learn beforehand what other employees are making. Catch the boss in a good mood, and preferably alone. Read a few articles on how to get a raise to make the whole process easier.

3. You Forgot Your Wallet

True story: On a first date in a fancy restaurant (oh those first dates), I looked down at my car 13 stories below and realized my wallet was in it. The elevator was in plain view, so I went to the bathroom and snuck down the stairs as fast as I could, returning out of breath with the wallet a few minutes later.

What if your wallet is at home? You might try going to the bathroom to call a friend who can then “coincidentally” run into you at the restaurant and suddenly remember that money he owes you (okay, that might be from a movie).

But you’ll probably have to confess and ask your date to pay. Approach it as a funny incident, and repay him or her as soon as possible. To make an embarrassing moment into an example of your problem solving abilities, see if you can transfer money from your PayPal account to your date’s account right then and there.

If you’re with a group pull aside a friend and quietly ask for a loan.

4. No Cash for a Tip

Now that we use cash less than ever it’s easy to forget to keep some bills in your wallet, and easy to forget that valet drivers and others can’t take a tip in the form of a credit card. What can you do when that embarrassing moment arrives and you have nothing to offer?

Apologize, of course, but don’t embarrass yourself more by saying “I’ll get you next time.” You both know there may never be a next time. Excuse yourself and go get some cash, and then tip generously.

5. A Friend Owes You Money

A loan is not a gift and to the extent you make that clear before you lend money, your friends are less likely to stiff you. I charge my friends interest, and tell them I never lend again if I’m not repaid on time.

What if you’re not a cold-hearted loan shark like me? Well, a sudden and public demand for repayment is bound to be awkward, and might not work anyhow.

Instead, send an email to the friend reminding him that he said he would repay you by (insert date here), and you really need the money, so you’ll be coming over to collect at (insert time and/or day here). This strategy makes it clear you plan to collect and gives your friend time to get the money.

6. Dealing With Panhandlers

The pope advocates giving to panhandlers while officials in many cities claim that doing so makes matters worse; they suggest giving to organizations that help the homeless instead. In any case, it is uncomfortable when you’re directly asked for help but you aren’t sure you want to give anything. So what can you do?

This one is a personal matter. If I feel money will help I’ll give something. But if, like me, you live where there are many homeless people and your financial resources are limited, you also have to get used to politely saying “sorry, not today,” or something similar.

7. Group Pressure to Contribute Money

Everyone at work is chipping in $20 to buy a present for a departing employee, but you really don’t want to contribute. Or you’re facing a fundraising request for a cause you don’t believe in. What do you do when a group you’re part of pressures you to part with your money?

A long term strategy is to consistently tell people that you just don’t do the group thing. You’ll be criticized less if you have a known policy than if you pick and choose when to give.

As a short-term strategy you can say you already planned to buy a gift on your own or donate individually. The advantage here is that you can spend less on your gift or donation.

8. Asking Parents for Money

Turning to your parents for financial help can be uncomfortable to say the least. Fortunately there’s a lot of advice online to help you out, even if you’re asking mom and dad for money to buy a house.

Having borrowed money from my parents and lent money to them, I can tell you what worked for us: We kept it all businesslike. If it’s a small loan for a short time specify exactly how and when you’ll repay it. If it’s a larger loan put it in writing with very specific terms, and pay interest.

9. Deciding Who Pays On a First Date

According to eHarmony, men pay the bill 68% of the time on a first date. Of course statistics don’t mean much when the check arrives and you both stare at it for an a moment too long… and then nearly break your fingers reaching for it simultaneously.

Generally the person who proposes the date pays the bill. But even if you’re the one asked out you can reach for the check. If your date stops you and says “I got that,” just say thank you. If you end up paying it you at least learned something about the person in front of you.

10. Group Meals

Every time I’ve eaten a meal where one bill was handed to the group at the end, there has been a problem. The money collected doesn’t add up, or results in an embarrassingly small tip, or the bill is split evenly despite the fact that some of us ate cheap entrees while others ate expensive ones.

Getting into a big argument isn’t worth the trouble or embarrassment, so what can you do when faced with a group bill?

Try this: Tally your meal cost with tax and tip, write it out on a scrap of paper, and set that on the table with the money. Say nothing more and go to the bathroom while the rest of them figure out their shares.

Try to avoid group meals. Or arrive early and start your own tab at the bar, so you can later sit with the group but pay individually.

Some restaurants refuse to provide individual bills for a large table. If they can’t handle a simple bill for each person go somewhere else if possible (and I would let let the manager know why, but that’s just me).

11. You Can’t Afford to Be a Bridesmaid

The cost of being a bridesmaid can easily top $1,000. A bachelorette party costs a bridesmaid an average of $400, and then there’s the dress, hair styling, accessories, and more. But what can you say to a friend when you’re asked to help her get married? suggests several ways to just say no. First, don’t put off the decision; that wouldn’t be fair. If you have a scheduling problem explain it (and I’m not going to suggest that you quickly make a dentist appointment, but it would be much cheaper).

Otherwise explain that for your own personal reasons you just can’t do it. In other words make it about you, not her. You might also soften the blow by offering to help with the wedding in some other way.

12. First Money-Talk With Your Significant Other

The first time I lived with a woman I set up a system where we each put money into a jar weekly and then paid bills out of it. Was it awkward to explain that? Yep. But only briefly.

It’s less uncomfortable to have that money talk as soon as possible, rather than wait for problems. According to the experts, couples who discuss money are less likely to get divorced and more likely to be wealthy. So…

  • Schedule a time to talk
  • Make it a fun event (a “money date”)
  • Focus on goals rather than bills
  • Include an advisor if necessary
  • Work to understand your significant other’s perspective

13. Splitting Bills With a Roommate

You split the water bill evenly but one of you takes hour-long showers. Or you have to cover the rent and then wait weeks for your roommate to reimburse you. There are all sorts of potential money problems with roommates, and it can be awkward to deal with them, especially if you are good friends. What can you do?

If possible, don’t split bills. Rent a place with most or all utilities included. Or rent a place yourself and then sublet to your roommates with all utilities included (and then just raise the rent a bit if the showers are too long).

Prevention is best, but if you’re already in the mess you’ll have to talk. Make it non-confrontational. Instead of criticising your roommate explain that you have different expectations. Ask if she can do things differently or if you should find a new roommate.

14. Discussing Wages During an Interview

The interviewer asks, “How much do you expect to make?” and you know if you go too high you may not get the job. On the other hand, I once said “$9 per hour” when they were actually paying $11 per hour. That probably hurt my chances for future raises. So how do you more-confidently talk about wages with a new employer?

The Interview Guys suggest developing an “executive mindset,” so instead of being a “job seeker,” happy to get anything, you’re a professional that the employer will be thrilled to have on the team. Approach the money issue as a negotiation, and be very prepared so you know beforehand what an acceptable wage is.

15. Hanging Out With Wealthier Friends

You’re with a wealthy friend and stop for a bite to eat. That’s when you discover that the cheapest meal at his favorite restaurant costs five times as much as you normally spend. Ouch!

One or two expensive mistakes like this probably won’t hurt you too much. Just pay the bill. But prevention is the long-term solution to the financial problems of hanging out with rich friends. Avoid situations you can’t afford and be honest about why. If asked to join a friend on a trip to the Super Bowl, tell him you really can’t afford to spend thousands of dollars.

If friends offer to pay, accept and say thank you, unless you’re not sure exactly what they’re paying for. A free plane ticket to Aspen doesn’t help much if you can’t afford the hotel room or lift tickets.

Another solution is to initiate get-togethers, so you can choose activities that fit your budget. Rich or not, your friends might enjoy a beer during happy hour, a hike to a waterfall, or a football game with chips at home.

Unfortunately, sometimes people with money really don’t understand the financial limitations of others. If that’s the case — if a wealthy friend keeps pushing you to join him in activities you can’t afford — you may have to limit the friendship.

Tell us about your most embarrassing money situations, and what would you do differently if faced with them again. And keep on fugaling!

Get Paid To Take Pictures Of Your Receipt: The Ibotta app is a mobile app that pays you to scan your receipts. Earn cash back at restaurants, grocery stores and even online purchases. Not only that, but you even get a $10 bonus when you scan your first receipt within your first week and use promo code qFTVA. The best part? It's 100% FREE.

Leave a Reply