13 Ways to Deal With Awkward Money Situations Without Breaking A Sweat

Have you ever had difficulty discussing money with your friends, family, colleagues, or significant other? 

Money, along with politics and religion, can be taboo topics. The awkwardness of money arises in many situations, adding discomfort, causing envy, and providing stress in relationships. In extreme cases, distrust may lead to financial infidelity, marital discord, and divorce.

Learn to be comfortable dealing with these issues in everyday situations without breaking too much of a sweat.

1.  Gaps in Income To Your Friends

Your best friends may take different career paths after school and be in different economic circumstances than you. You may need to make other choices when getting together with them as a group or individually. Don’t shy away from being together, whether eating out, shopping, or vacationing, but suggest outdoor experiences that may be less costly.

Gaps in income can cause wedges in your friendships, but prioritize what is most essential, such as dinners, shopping, or vacations. Be honest with your friends if you recognize that you cannot afford to spend as they do. You can be direct, saying, “I cannot spend X for dinner, but I’ll order a salad,” or decline, saying, “I am saving money to do X, and I am somewhat limited now.” It takes some finesse to navigate, but it is worth it to be with good friends. Find out beforehand and learn how to reciprocate, such as having friends for dinner.

2. Shopping With Others With Different Spending Habits

Ever go shopping with friends for clothes, and bring garments home you didn’t want? When I was younger, I would return items I knew I wouldn’t wear. Later, I realized my friends wouldn’t care if I did not buy their suggestions.  Stick with your spending habits instead of trying to “Keep up with the Joneses,” or shop with like-minded friends if it makes you uncomfortable. The point of shopping is to have a fun afternoon with friends, and overspending for an outing will be a regret later on. 

3. Lending Money To A Friend

Being asked to lend money to a friend or family can be awkward. Just because you earn more does not necessarily mean you have to take a loan. You may have many uses for your money, notably savings, and investments. Sometimes it is a small amount, such as when a friend forgot a credit card, the card didn’t work, or it’s a negligible amount. It happens to everyone, and most people will pay you back. 

However, if it is for a friend having significant money problems, you may get caught up in their difficulties. They may ask you after their family or other friends have declined. Continually borrowing from others may be a red flag. You can politely and promptly say no, or it may be your rule with your significant other not to make loans.

4. Dealing With a Roommate Who Can’t Pay Rent 

While sharing an apartment or house is a great way to save money and have independence, there will inevitably be challenges if you have a roommate(s). Living with roommates can bring out inelegance when dealing with money, so learn more about the people you may room with. Everyone’s name should be on the lease to split the responsibility or have separate leases divided by the room and communal spaces. A roommate agreement (RA) may be an excellent way to divvy responsibilities, accept rules, and conflicts, and set up a protocol for known issues. An RA may not be legally binding as your lease.

5. Splitting A Bill With A Large Group

Going to dinner with a large group of friends or colleagues can be challenging. splitting the bills can be difficult. Typically, you’ll divide the bill equally in cash or credit cards. Make sure you can cover your account unless the event was spontaneous.    It takes some finesse to navigate, but it is worth it to be with good friends. Find out beforehand and learn how to reciprocate, such as having friends for dinner.

6. Declined Credit Card

Ever had a credit card declined at a restaurant with friends or colleagues? It can be pretty awkward, primarily if you treat everyone. Don’t get flustered. If you have another card or a debit card, use it, or call a family member to use their card. If you can’t don’t those alternatives, ask your server for the decline code, and contact the customer service number on the back of the card. Depending on your card company, and your payment history with them, they may extend money in the short term.

7. Dinner Companion Not Leaving A Proper Tip

Tipping etiquette has become tricky, but leaving your server, assuming they did their job the proper amount, is anticipated and appreciated. Sometimes, your dinner companion feels differently and provides an inferior tip in one of your favorite restaurants. Rather than cringe, you can fix it and feel better about it. Even if it’s not your favorite dining place, you could say, “I don’t think we’re leaving enough,” or “The meal was quite good, and I’ll leave some more.”

8. Asking Your Boss For A Raise

There should be no issue asking for a raise from your boss, especially if you have been doing an excellent job for a reasonable time. Before doing so, ensure you are prepared to advocate for yourself with legitimate examples of your work. 

You may have found out your peer is making more money than you do for the same job. However, comparisons should not be part of your conversation with your boss. Instead, be informative, flexible, and respectful. Focus on your skills and achievements, and point to specific examples where you exceeded expectations.  

9. Avoid Recommending Someone For A Job You Don’t Know 

When working at a desirable company, a friend may ask if you can put in a good word for them or their friend to get an interview. Think before you do so. If they are qualified for the job, recommend them for an interview. However,  it’s better to pass on someone you believe has shortcomings, a lack of experience required for the job, or sense some red flags. You may be responsible for bringing in an unqualified person.

10. Talking With A Soon-to-be Spouse or Partner About Money 

When you are first dating, you don’t usually talk about what you earn or deal with money. However, as you become more serious, you should learn about each other’s values, including financial priorities. How financially compatible you both are matters in the short and long run. It is alright if you both earn different incomes, but you should share your financial and life goals.

Avoid awkwardness about money later on by being open and transparent and any bad money habits you have. Hiding financial problems could lead to different circumstances, distrust, and divorce. Deal with it gracefully and early so you can resolve the issues together.

11. When People Question You On Your Money

One sensitive area about money is when others ask you about your money, sometimes after you’ve had some success in your career. Instead of asking you how much you earn, they may believe it less taboo if they ask how much your house is worth, your investment portfolio, or what you paid for your apartment.  Those questions are cringe-worthy, especially if asked in front of others.  

 I recall getting a few questions that made me wince:

What are you making these days?” 

I thought you’d be living at least on Fifth Avenue. Why aren’t you?

Most people understand boundaries and don’t need to know the answers to those unanswerable questions. It’s best to smile and say, “I’d rather not share that.”  

12. Who Pays the Bill on the First Date?

The first date is always awkward, so when it comes to picking up the bill, it compounds uneasiness. Typically, the one who initiated the date may be the most responsible person to pick up the tab. However, if two people agree to meet and go out, you can either share the bill or someone does the driving. Enjoy your time, and work out the responsibility if you have more dates together.

13. Giving To Charities At Work

Friends or coworkers may ask you to contribute to their charities at work or on social media. It may be small amounts or to a worthwhile charity. However, sometimes there are too many people asking for support simultaneously. You may have several charities on your list. Let others know you appreciate their including you, but you give money to your charities.

Final Thoughts

We experience awkwardness when dealing with everyday money situations. Talking about money is a sensitive topic but frequently arises with friends, families, coworkers, and bosses. Be open, direct, and honest when you are with others. Learn to say no when people ask for money if you cannot make loans or give to charities.

Your financial situation should harmonize with your beliefs, values, and abilities. You don’t have to compromise when you are with others. Don’t hesitate to ask for a raise but learn how to negotiate. The awkwardness of money can be stressful, provoke distrust, and ruin relationships. Always deal with money problems head-on with significant others. Like Robert Frost said, “The best way out is always through.”

This article was produced and syndicated by The Cents of Money.


10 thoughts on “13 Ways to Deal With Awkward Money Situations Without Breaking A Sweat”

  1. There is an awkwardness with money that comes from being perceived as rich. It labels you as being out of touch with working people’s lives. Because I ran the largest employer in our part of the state it was assumed I was paid astronomically, which wasn’t true. I lived in a modest house, drove modest cars and had zero debt. While I was pretty good at managing money it was easy to tell that nobody wanted my opinion on finances, because as a rich guy I couldn’t relate. My rich friends didn’t think I knew anything about money because I lived too frugally, they thought I was some kind of eccentric. So I just kept quite. Nice post!


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