Where’s My Money? Season 6, Episode 2
Season 6 of the multi-award-winning podcast Where’s My Money? has arrived to keep bringing you the financial content that helps you be better with your money.
enable.me partners with rova to bring this podcast to life and stimulate the conversation about finances with everyday Kiwis. Where’s My Money? follows the story of Reagan – a man chasing the Kiwi Dream but feeling stuck living month-to-month – and his discussions with the experts about what he may be doing wrong and how to fix it.
One man. One million dollars of debt. One podcast to find a way out.
Communication is commonly touted as one of the core components behind any successful relationship – whether it be friendship, business partnership, or a long-term romantic relationship. Yet discussing the simple topic of ‘money’ is just as commonly described as the most difficult part of meeting someone.
It’s understandable when we consider how deeply unique, personal, and interlinked our money beliefs are with our behaviour. Our actions today can help or hinder progress. Our beliefs today can inspire or limit long-term potential. And layered over all of that is identity – how we see ourselves, what we think we deserve, and what we fear losing.
When the conversation also involves romance – particularly if you’ve just met someone new and are still figuring out how they like their coffee – navigating what we feel is right and what we know is important can feel risky. It can deflate desire and end a connection before it begins.
On the flip side, it’s a crucial discussion. More than a few will know the impact of having the conversation two years too late. So how do you vibe-check financial compatibility when you start dating without sending someone running for the hills?
In this episode of Where’s My Money?, host Reagan White talks to the experts to find out.
Sara Chatwin, a registered psychologist, MindCoach and social commentator from MindWorks, joins Elise Dalrymple-Keast, CEO and Owner of Compatico, a premium curated matchmaking service for ages 30–70+, and enable.me Financial Coach Shelley Palman on the podcast to share their experiences and knowledge about money and relationships.
Opposites attract – how do you navigate that with shared finances?
Psychologist and MindCoach Sara Chatwin begins by unpacking the psychology of dating when it comes to shared finances. One of the biggest influences, she explains, is how you were raised around money – and how that may differ from your partner’s experiences.
We all arrive in relationships carrying financial scripts written long before we met each other.
“These two people come together from very different backgrounds… there may be things that are very in sync, because often we’re attracted to opposites, but often we’re attracted to people who have a similar set of values,” Sara says.
That tension between similarity and difference is where things get interesting. Under the umbrella of finances – money matters, spending habits, saving goals, debt tolerance, lifestyle expectations – there is almost always some rub.
“You could imagine there’s going to be some dissonance, some areas of disagreement, and a lot of areas of confluence.”
The key, she highlights, is communication. Not surface-level agreement, but honest conversations about what each partner wants to achieve and why – especially when money is tied up with something far deeper than dollars and cents.
Money is rarely just money; it’s often also a reflection of ourselves and what we want in a partner. As Sara puts it, “self-esteem, self-loathing, self-loving – it’s all tied up.”
Bringing up the money topic on a date
Knowing that money conversations involve strong emotions – and potentially conflict – how soon is too soon to bring it up when you’re dating?
Elise Dalrymple-Keast brings her experience from the matchmaking world into the discussion. As CEO of Compatico, a human-to-human matchmaking service, she sees first-hand what people are actually looking for when it comes to financial compatibility.
She says people are looking for authenticity. They want someone who is upfront about where they are in life – including financially.
“What are you looking for in terms of someone’s financial status?” she asks her clients. “And most people say, I’d prefer someone who’s on par with me and can keep up.”
What “on par” means varies. Some clients may have a home or a solid nest egg and want someone in a similar position. Others may be incredibly successful business owners with net worth in the millions – and they want someone who can, as she’s heard more than once, “sit up the front of the plane with them.”
Because that’s who they are, and what they want. But this is also evident of core financial behaviours; a clear plan, goals, ambition, and self-awareness.
Financial conversations with a partner are fundamental, especially if you’re considering long-term goals and planning. You don’t want to invest time you can’t get back, only to discover that the end goal looks completely different for each of you.
“Especially coming to it later in life,” Elise explains. “If you’ve gone through a separation, if you’re divorced, you’ve built up quite a nest egg for yourself, and also you’re really busy – you might have kids, you might have work…”
While our passion for the pursuit of happiness and lasting love is rarely muted by time, few of us have the time or interest to swipe endlessly through apps or meet up with people who have zero in common with you and zero shared interests. Understanding who you are, and what you want, are essential to minimising wasted time.
“Make sure you are really happy within yourself first,” she says.
Start by knowing yourself
Before you bring money into a romantic conversation, you need clarity on your own position.
The best preparation for a money discussion – whether with someone you’re dating or already in a long-term relationship – is self-awareness. It’s vital to understand your own money values because they will shape what matters to you in a partnership.
As enable.me financial coach Shelley Palman says, “It comes back to being really clear about your own money values.”
“So really understanding yourself and going, okay, what are my goals? What do I financially want to achieve? Do I want to retire early, get mortgage free, help my kids?”
These questions might feel rigidly practical, but they’re often deeply personal and tied to our emotions. Getting on the same page about long-term aspirations can be the difference between achieving your goals together – or watching them remain goals forever.
Differences in opinion can bring valuable perspective. Provided the mentality is “me and you versus the problem” – not “me versus you” – those differences can strengthen rather than fracture a relationship.
And as Reagan adds, “You don’t just inherit assets when you become one, you actually inherit someone else’s liabilities.”
Which is why these conversations matter. Because money is not just about numbers, it’s also about your lifestyle, security, identity, and vision for the future. It’s about whether your goals and dreams align – or quietly compete and potentially sabotage.
When it comes to dating and money, as with most things in life, creating the life you want and building long-term happiness starts with knowing yourself. Then having the courage to talk about it.
Watch the full episode for all the advice about money and dating:
Disclaimer: The Where’s My Money? podcast and the information shared by host Reagan White and his guests does not constitute individual financial advice. If you’re interested in receiving financial advice, you can book a consultation with an enable.me coach. Costs apply.
