Turning Dating Disasters into a Marketable Podcast Brand with Andrew Small

If you’ve dipped a toe into online dating over 40, you’ll know it’s… a lot.
Time-wasting. Soul-sapping. Sometimes hilarious. Often exhausting.

In this episode of The Meaningful Marketing Podcast, I sat down with Andrew Small, host of the Over Forties Dating Podcast – Real and Unfiltered, to talk about dating apps, ghosting, coffee dates that go nowhere – and how he’s turning those lived experiences into a powerful, marketable podcast brand.

This blog unpacks what we discussed, the reality of online dating over 40, and the surprisingly useful life and marketing lessons inside Andrew’s story.

Why Online Dating Over 40 Feels Like an “Absolute Effing Nightmare”

When I asked Andrew what his experience of online dating over 40 has been like, he didn’t sugar-coat it:

“A freaking nightmare”
“Time wasting”
“Soul sapping”
“Exhausting”

After a 15-year marriage, separation and divorce, Andrew found himself back “on the market” in his early 50s, with three kids, 50/50 custody and a good life on the Gold Coast. Like so many midlife singles, the dating apps felt like the obvious next step… but no one hands you a rule book.

He had to:

Learn how to create a profile from scratch
Navigate filters, catfishing and fake photos
Adjust to the constant ping, ping, ping of matches and messages
Deal with the emotional rollercoaster of hope, rejection and confusion

Most people in their 40s and 50s didn’t grow up with apps. You’re dealing with divorce, kids, businesses, mortgages – and suddenly trying to decode emojis, ghosting and AI-powered filters.

It’s no wonder online dating over 40 can feel like an absolute effing nightmare.

Profiles, Photos and First Impressions: What Actually Matters

One of the first things we spoke about was profiles – because whether we like it or not, that’s where it all starts.

Andrew deliberately avoided the cliché “holding a fish” photo. Instead, he chose pictures that reflected his active, real lifestyle:

One at the gym
One cycling
One playing golf

Nothing overly staged. No extreme filters. Just: “This is me. This is my life.”

On the flipside, I shared how, whenever I meet a man who’s on the apps, I say:

“Quick, show me your feed, I want to see what my competition is like.”

It’s a little joke… but it’s also a competitor analysis.

Looking at the other profiles made me realise how different mine looked – the photos, the energy, the honesty. And that’s a big lesson for both dating and marketing:

You can’t stand out if you don’t know what everyone else is doing.

Takeaway for online dating over 40 (and business):

Choose photos that actually look like you
Show your real lifestyle, not a fantasy version
Be aware of the “market” you’re in and how you’re positioned

Communication, Values and Emotional Intelligence in Midlife Dating

We also talked about communication – not just texting, but knowing who you are and what you stand for.

On the apps, you’re communicating through:

Visuals – your photos, your body language, your background
Written words – your bio, prompts, messages
Energy – the way you reply, how fast, how thoughtful

I shared this in the conversation:

If you’re a poor communicator, and you don’t know how to express yourself or understand who you are and what your fundamental values are, you’re going to find it very hard to connect with someone.

Andrew admitted he’s not a big texter. He’ll literally tell women upfront:

“You’re not going to get the real me by text.”
“Let’s jump on a phone call and see if we vibe.”

And honestly? That makes sense. You can text someone for days, build an emotional attachment, and then meet in person and realise the energy just isn’t there.

Healthy communication flow for online dating over 40:

Short text chat – basic vibe / safety check
Phone call – hear tone, humour, presence
Quick coffee – see if there’s real-life chemistry

In marketing, this is exactly what we do:

Scroll-stopping content (profile)
DM or enquiry (text)
Discovery call (phone/Zoom)
Working together (in-person experience)

The better we communicate, the better we connect – in love and in business.

Red Flags: Ghosting, Catfishing and Love Bombing

No conversation about online dating over 40 is complete without the big three:

Catfishing – heavily filtered / old photos, or people who look nothing like their profile
Ghosting – disappearing without explanation
Love bombing – intense affection, big promises, very fast… often followed by a crash

Andrew shared stories of:

Turning up to dates where the person looked completely different
People being stood up after making an effort to get ready and show up
How “ghosting” has weirdly become socially acceptable because it’s easier than being honest

I pointed out that we live in a world where:

It’s incredibly easy to block, mute or disappear
Social media normalises “unfriending” and “unfollowing”
Avoiding hard conversations is often the default

The problem? That behaviour is emotionally exhausting on both sides.

Protecting yourself in online dating over 40:

Don’t ignore your gut when someone is moving too fast, too intense
Be honest and kind when you’re not feeling it – even a short message is better than silence
Recognise when someone’s words and actions don’t line up

From Apps to Real Life: Where to Meet Like-Minded People Over 40

Online dating isn’t the only option. In fact, for many people over 40, it’s not the best one.

I shared my own approach to getting off the apps:

Joining Meetup groups
Finding cycling groups
Going on hikes
Joining a solo camping group with my camper van

Instead of endlessly swiping, I started putting myself in spaces where my kind of people already are.

This is powerful for a few reasons:

You see how people behave in real life, not just curated photos
There’s already a shared interest to talk about
You can build friendships and potential relationships without so much pressure

Dating and marketing share the same principle:

Put yourself where your people already are.

In marketing, that means:

The right Facebook groups
Industry events
Podcasts your audience listens to
Communities and memberships they already love

When you’re in the right room (or hiking trail, or coffee shop), connection becomes a lot easier.

“On the Market, In the Market, Enjoy the Moment”

One of my favourite parts of the conversation was Andrew sharing a mindset reframe he got from his psychologist:

On the market – emotionally and physically available
In the market – actively going on dates, joining events, meeting people
Enjoy the moment – dropping the heavy expectations

For a while, Andrew was going on 20–30 coffee dates a month. That’s a lot of time, money and emotional energy – especially when none of them led to a second date.

The mindset shift was:

Stop going into each date thinking, “Is this The One?”
Start treating it as: “I’m getting out, I’m meeting people, I’m having experiences.”
Focus on the experience being worthwhile, even if they’re not your person

This takes the pressure off online dating over 40 and helps you:

Stay open
Stay curious
Stay less attached to each individual outcome

Turning Dating Disasters into a Marketable Podcast Brand

So why turn all of this into a podcast?

Andrew’s Over Forties Dating Podcast – Real and Unfiltered is built on:

Real stories – the funny, tragic and ridiculous moments in midlife dating
Relatability – letting people know they’re not alone in their experiences
Education – bringing on psychologists, dating coaches, life coaches and everyday people
Hope – offering guidelines, warnings and encouragement for those still in the trenches

From a marketing perspective, what Andrew’s done is genius:

He’s taken a painful, messy life area
Turned it into valuable content
Then built a brand and platform around it

Your mess really can become your message – if you’re willing to be honest and intentional about it.

What Online Dating Over 40 Can Teach Us About Marketing

Throughout our chat, there were so many parallels between dating and marketing:

Competitor analysis
- Dating: looking at other profiles to see how you compare
- Marketing: understanding what else your audience is seeing in their feed
Authentic positioning
- Dating: no filters that completely change your face
- Marketing: don’t sell something you can’t deliver; no “catfish offers”
Qualifying early
- Dating: text → call → quick coffee to see if it’s worth more time
- Marketing: DM → call → proposal, so you only go deep with the right people
Being where your people are
- Dating: Meetup groups, interest-based events, activities
- Marketing: niche communities, platforms and spaces where your ideal clients hang out

When you understand online dating over 40, you start to see that what most of us really want is the same in love and business:

Clarity
Honesty
Consistency
Real connection

Practical Tips for Online Dating Over 40

To wrap the content of the episode into some simple actions, here are a few tips inspired by our chat:

Choose realistic, current photos that show your actual life
Do a quick “competitor analysis” of other profiles to see how you stand out
Move from text to phone as soon as possible
Keep first meets to coffee or an activity, low pressure, easy exit
Learn to spot red flags like catfishing, ghosting and love bombing early
Join interest-based groups so you’re not relying solely on apps
Adopt the mindset: on the market, in the market, enjoy the moment

And if you’re sitting on your own “dating disaster” or “life mess” wondering if it could become content, a blog, a podcast or even a brand – Andrew is living proof that it absolutely can.

If this conversation resonated with you, go and check out Andrew Small’s Over Forties Dating Podcast – Real and Unfiltered, and listen to our full episode of The Meaningful Marketing Podcast where we dive even deeper into the wild world of online dating over 40 and the marketing lessons hidden inside it.

Marketing feeling a bit scattered?