Why it’s so hard to talk to your loved ones about finances

Update as of 31 August 2023: This content was sponsored by MoneyOwl at the time of publication (23 November 2021). MoneyOwl has just announced on 31 August 2023 that it is winding down its financial advisory business and all commercial activities will cease by December 31, 2023. To find out more, visit their microsite here.

Talking to the ones closest to you about finances is hard.

Trust me, I speak from personal experience.

Since I’ve embarked on my own financial journey back in 2014, I’ve tried to bring some people along with me, often with little success.

You might have faced similar situations. This could be elderly parents refusing to buy insurance, or a prospective spouse being defensive about how much money they owe.

While this is incredibly and undeniably frustrating, over the years I’ve come to understand this behaviour a little better.

Let’s talk about some of the barriers to communicating with those closest to you:

The biggest one: closeness-communication bias

Even if you communicate for a living, it might not necessarily mean you’re great at communicating with your partner (just ask my girlfriend).

Research has shown that we unconsciously tune out people we feel close to because we think we already know what they’ll say.

This is known as the closeness-communication bias. We overestimate our ability to communicate with people close to us.

We assume they’ll automatically get what we say, and there isn’t the need to do all the things that make us good communicators.

It’s also frustrating if someone close to you can’t see your perspective about money, because you’d expect them to ‘get’ you.

In this sense, we ‘let down our guard’ and make many communication mistakes that we otherwise wouldn’t have made.

Think about the times your partner expected you to ‘read their mind.’

Now, consider that you probably have done so too!

People can have fixed mindsets about money 


It’s common for people to hold a fixed mindset about how one should handle money. They can be single-minded about it.

Perhaps it’s a belief inherited from their parents, such as ‘money is the root of all evil’, ‘always pay off debt first’, ‘never spend your principal’ or ‘money can’t buy happiness.’

The validity of all these ideas is another thing altogether, but it becomes a problem when someone refuses to accept other perspectives on money.

If you’re dealing with someone older than you, things get even more complex. Especially in cultures where younger folks are expected to listen to their elders.

I’ve been shut down before in conversations about money simply due to my age with the classic ‘eaten more salt than rice’ argument.

It’s also common for people to think less of you because of your age, gender or even profession. This hurts even more when it comes from people who you think will value your opinions.

It’s often not just about the money

Depending on upbringing and culture, your partner/parent/friend could find your questions about money incredibly intrusive, inappropriate and rude.

For many people, talking about money brings about deep feelings of inadequacy, insecurity and shame.

That’s why seemingly innocent questions can trigger explosive reactions.

Here’s an instance I particularly remember.

Once, my parents watched a TV drama where the son kicked his parents out of their own home after taking their money.

Over the years, the newspapers also had a slew of articles (here, and here) about elderly Singaporeans being abandoned by their middle-aged children.

For years after, my parents would frequently make passive-aggressive comments, suggesting that I might one day do the same. My dad even went as far as to say I would inherit nothing whenever I tried to talk about their retirement.

On the surface, this seemed like an issue about money.  In reality, this was their fears about abandonment and potential loneliness causing them to lash out. In this case, trying to solve the problem just from a money point-of-view would be addressing the symptom, not the cause.

Whether it’s about opening a joint savings account, or asking if your parents have done up their will – there are often deeper issues that make talking about money difficult.

These are high stakes, high-risk conversations


If you talk to acquaintances about money, the stakes are low. They can go into bankruptcy and debt, and you’d be relatively unaffected.

You don’t care for them, either. There’s no skin in the game.

However, when you are close to someone, their lives are intertwined with yours.

Why? First of all, their financial situation will undoubtedly impact yours – if your parents get scammed of their life savings, you’ll be saddled with the costs of looking after them.

Secondly, you care for them. You can turn the page on the story of strangers struggling with money. It’s harder seeing your sibling go through financial hardship.

Thirdly, you have to live with the impact of your conversation long term. You can piss off a stranger by being brutally honest. You’ll never see them again.

But if you speak your mind to your partner and offend them, there are lasting consequences.

You’ll have to see them every day. They might bring up what you said 5 years into the future.

Is it any wonder we put off important conversations about money?

Overcoming the difficulty of talking about money

Small steps first. If you read this blog, you’re probably part of a minority who nerds about their finances. Not everyone is ready to discuss whether they’ve topped up their CPF right off the bat.

Try telling your partner what you’re doing with your money, then wait and see if they reciprocate.


Instead of:

“How much money do you have!?!!?”


“I’m trying to save this $100,000 by 30. What are your own financial plans like?”

“What do you think about this savings goal? Do you think it’s realistic?”

Tell them why you want to talk about money. Few intelligent people enjoy the process of doing something for no reason at all. The same goes for money.

By letting them know your motivations behind it, you provide context to why you’re starting the conversation. Good reasons include:

  • You are serious about this relationship, and money is a central part of it
  • [For parents] You are worried about their own retirement

Lead by example. Competence is credibility. Now that I’ve got my finances sorted out, I find it easier to talk to my parents or my partner about money matters. It’s easier for people to dismiss your views when you are perceived as incompetent with money.

Withhold judgement, blame and jumping to conclusions. When I first started this blog, I was guilty of judging people about their money decisions. What I’ve found is that if I truly want to help others, I should withhold judgement instead. I think this applies to anyone who wants to have an open conversation about money.

You don’t want to go in guns blazing: ‘OMG? You only have $10,000 at 30?!?!’

Read widely and get many different opinions. There are great, free financial resources available today to get a second opinion.

Get a neutral third-party mediator. Finally, to overcome the closeness-communication bias, it’s worth considering a third-party mediator.

Inevitable common choices include a close friend or even parents – but we think this is generally a bad idea as it’s hard for them to be neutral. (You can also DM us but sometimes we don’t reply because we’re really busy)

In circumstances like this, speaking to a fee-based financial adviser makes sense.

You only pay for their time, and they don’t earn any commission, so that removes any potential conflict of interest (and unsolicited upselling). Kinda like a financial therapist.

The way we see it, you pay for three things:

  • Financial advice
  • Privacy from people close to you
  • A neutral environment to discuss financials openly with your partner (Which would otherwise be difficult)

After you receive said advice, it would then be up to you to follow up.

Discussing money is necessary for every serious relationship


Make no mistake, money is not everything.

But if you want to live a comfortable life in a major urban centre in the 21st century, then it is undeniably a lot of things.

Trust me, I know there are many things you’d rather talk about with the ones you love.

After all, it’s far easier to talk about the latest Netflix series or which social media saga there is. Or where you might want to travel to when COVID is over.

I’m guilty of avoiding these difficult conversations myself.

We say things others might not like hearing because we care for them; we care enough that we are willing to potentially hurt their feelings.

When we open up and allow others to get close, we reveal our vulnerabilities, insecurities and imperfections.

It’s easy to let emotions cloud the way we communicate with our loved ones, so we must be tactical when it comes to these things.

We are taking the risk of upsetting someone, so we should at least maximise our chances of success by being sensitive, preparing, and trying to solve the problem.

You and your loved one’s futures are at stake.

Speak truthfully, speak tactically, and speak frequently.


Stay woke, salaryman.

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2 replies to “Why it’s so hard to talk to your loved ones about finances

  1. I think it just depends on your family. My dad was very proud of his investments. When his portfolio first passed a million dollars he proudly told my brother and me he was a millionaire. For an average income earning man who grew up during the great depression in the US that was quite an accomplishment. He showed us his spreadsheet where every investment he had was tracked. He taught us how to buy treasury bonds from the government, how to buy mutual funds and to pay ourselves first. He and our mom never argued about money and never bought a thing on credit except their house that they paid off early. Consequently my brother and I grew up being good with money, becoming multimillionaires on our own. My wife and I were open about money with our kids too and they have become financially responsible adults. I think because money was never a problem, we always had plenty and never had any debt or car payments or credit card interest, then talking about money had zero shame or fear attached. Its like a fitness person talking about working out, they love to talk about it. But a sedentary person avoids talking about exercise because they feel guilty about it.

  2. “For years after, my parents would frequently make passive-aggressive comments, suggesting that I might one day do the same. My dad even went as far as to say I would inherit nothing whenever I tried to talk about their retirement.”

    Extracted the above paragraph to add my views. While you recognized the insecurity in your parents about what you might do to the them one day, it seems to me you have not done anything or much to allay their fears. Thats why “for years after” your parents kept bringing up the topic. They are giving you very strong hints about what you are not doing or not doing enough for them.

    If you feel that they dont have enough insurance coverage, buy and pay for their insurance. If you feel they dont have enough CPF, top up their medisave and retirement accounts. These actions will go a long way to allay their fears and make them more confident that you will not abandon them, or lessen the impact on them financially if you do indeed leave them to build your own family. And by doing these things for them, surprise, surprise, they may open up to approach you to talk about your finances. They would want to know if you could afford to do the things you do for them. And like all parents, they do want to leave something behind for their children (you).

    We are parents of two millennials and we do worry about their finances and in turn they are also concerned to not add to our burden. Sometimes, financial matters are best addressed by actions rather than by talking. Actions such as children giving allowances to their parents, topping up their retirement accounts, helping to pay for their medical insurance and treatment. With these actions, children will cement their parents’ trust and confidence in them. Parents will then not have second thoughts about bequething their wealth to the children.

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