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6 of the Most Uncomfortable Conversations About Money, Ever (And How To Have Them)

Lindsay Tigar  |  January 20, 2020

Talking about money can make anyone squeamish. But it’s necessary, and here’s how to do it.   

Financial matters are a reality of day-to-day life. But do we talk about it? Not if we can help it!

Yet, no matter how uncomfortable we may feel or how difficult it is to open the discussion, the more we talk openly, freely and vulnerably, the better equipped we are to handle anything and everything that comes our way. 

From parents and children to relationships and expenses, here’s how to navigate these chats confidently and effectively:

The one about money and love 

There’s nothing quite like the thrill of falling in love. Filled with visions of a promising tomorrow and marinating in the good-vibes of happy endorphins, your partner is always rose-colored through your lens. That’s what makes it hard to bring up the not-so-sexy question about their financial and debt situation.

You may want to avoid the topic, but talking it out can actually strengthen your bond. “Knowing this information will help you move forward as a couple,” explains Jeremy Straub, the CEO of Coastal Wealth. “Although these types of conversations can be awkward, they will promote healthy discussion and eventually help you both feel more secure in your relationship.”

Things you want to know before moving in together include each of your income streams, debts, and other requirements. No financial concern or consideration is too small if it feels significant to you. The idea is to find where you align and where there are differences. 

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One way to make the Big Conversation less scary is to suggest a night-in, with a bottle of bubbly to keep the mood light and relaxed. From there you can start discussing specifics. “Set budgets and expectations that make sense for you. If your partner recommends a budget that you’re not comfortable with, be honest. If you’re struggling financially, maybe suggest an at-home movie night or making food at home. If you feel that you’re buying all the cleaning products for a home you share with your partner, tell them you want to discuss shared expenses,” Straub says.

As talking with your partner about money becomes less taboo, the conversations will become easier. With open communication, so will finding ways to manage money that works for you and your relationship. 

The one before marriage and children

As your relationship evolves, your conversations must too — especially before you tie the knot and expand your family. With 50% of marriages failing due to financial stress, disagreements and mismanagements, coming up with a financial plan is just as important as pre-marital counseling, says financial expert and co-founder of, Tiara Zolnierz.

Before growing your family into a party of three, four or more, Zolnierz recommends coming up with a financial timeline to match family planning. To discuss: How will we pay for them? How long of a maternity and/or paternity leave will we take? Will we aim to pay for college? How will we handle kid-related expenses? 

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Talking openly and in-depth about big-money issues (like having children) will save you years of suffering and misery, Zolnierz says. And if you or your partner resists and can’t find the courage to settle in for these talks and dig deep? “It’s a major red flag and a sign that the love of your life might end up being the regret of your life.”

The one about friends and money 

We’ve heard the saying before: Friends and money don’t mix. But that’s an outdated statement in a time when women are fighting tirelessly for equality. Because the more we discuss our financial situations — income, expenses and so on — the more empowered we will feel to fight for change. And since there’s another saying about strength being found in numbers, let’s go with that and take the opportunity to have those uncomfortable but important money-matter chats with our closest friends.

In addition to being brave enough to ask about what our pals make when we are negotiating our own salaries, we should also discuss how we approach day-to-day expenses, according to psychologist Dr. Yvonne Thomas, Ph.D

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A natural place to start the conversation is when you’re out for a meal. Do you always split the check 50/50? Do you have a friend who often picks up the check without question? It’s okay to say if it makes you feel uneasy. “It is important to remember that whenever the topic of money is brought up with people close to you, it should be handled in a respectful, clear way so as to not offend the other person but to make your relationship with him or her even stronger,” Thomas says.

Another tricky convo to have, according to Carly Frieling, a financial advisor for Civic Financial/Northwestern Mutual, is asking earnestly about savings. Say for instance, a close friend just went on an expensive, dreamy vacation — and you’re curious on how they afforded it. Though at first it may feel taboo to ask, Frieling says a friendship is one of the safest places to share ideas, sans-judgement. 

“If you take the emotion out of the money conversation, and go straight to the point, the conversation won’t be awkward,” Frieling says. She suggests an ice breaker like this: “To make the conversation normal, simply ask, ‘I’m looking to go on a trip to XYZ place and I saw you just went on an incredible trip. Can you share one or two tips [of how you saved up for it or cut costs] that I could use?’” 

The one about inheritance

As we become adults, some of the burden of helping our parents manage their own finances may fall on us. We don’t have to agree with how mom and dad spend their money during their golden years, or even how money is divided in inheritance. But we do have to talk about it to ensure wishes are respected and protected. 

This frank discussion about what happens to their estate can seem morbid or make you feel greedy. That’s why it is important to be direct and calm when having this type of conversation — to make it clear you’re coming from a place of concern.

In a quiet, private environment, Dr. Thomas recommends saying something along the lines of: “I know this is an uncomfortable subject and it’s hard for me to even bring up, but we have to talk about if you have a will and if it is current. I just want to make sure that you have a will and that it includes everything in it you want it to. Or if you don’t have a will, you need to set up an appointment to talk to a lawyer to get a will made.”

The bottom line of course, is communicating how important it is to be there for our parents as they age, and that their hard-earned cash is spent how they want it to be, once they’ve passed.

The one about borrowing — and owing — money

Whether due to an unexpected expense, job loss or a tragedy, asking to borrow money from a friend, family member or partner may be your very last shot at staying above water. 

When this happens, Straub recommends taking the time to think through all the details. “When you ask the person to lend you the money, give them exact dates for when you’ll be repaying them. Will you make payments or pay everything back in one lump sum?,” he says. It can feel embarrassing to be vulnerable, but the more facts you provide — rather than emotions — the better someone will feel about helping you out. 

If it’s you on the other end of the conversation, be honest. “If lending them money will get in the way of your finances, let the person know that now isn’t a good time. Or, if you simply don’t feel comfortable with lending money, just be upfront,” Straub says. 

If, however, you are in a position to lend money, be sure to outline expectations for the person borrowing the money — and stick to them. “You don’t want to be in an awkward situation with a friend or family member who never repaid you. If you do have to have an awkward conversation, be polite, but direct,” he says. Offer to set up a repayment schedule if the person is unable to give you the money back in one lump sum. “Remind them frequently and don’t let too much time pass,” Straub says. Otherwise things will get really awkward.

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The one we have with ourselves 

We all do it: We compare ourselves to our friends, who seemingly make more cash than we do. Or a colleague who negotiate a higher salary, even though we do the same amount of work. How about a partner, who we love and admire, but definitely has a higher income? 

When thoughts like these creep into our heads, it’s time for an uncomfortable money conversation with ourselves. 

Comparison is the thief of joy, and, as Frieling points out, nothing is ever exactly how it seems: You may never know someone else’s full financial picture — the dollars and cents behind their house, fabulous travel or amazing wardrobe. 

Instead of making outward comparisons, focus your energy inward: Follow your own timeline, strive to meet your own goals. As long as you are living a life within your means that makes you happy, there’s no purpose in keeping up with the Joneses, who hey, may being using a hefty Instagram filter to paint a prettier picture than reality. 

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