What I wish I’d known about dating in my thirties

“Maybe it’s never too early to know what someone wants in life when you start dating at (almost) 30.”

I wouldn’t be writing this unless I wanted to help others out there facing the same conundrum. In the middle of this year, I found myself at the end of a three-year relationship with a guy I considered my ‘forever person’. I was faced with the stark reality of moving back into my nostalgic childhood bedroom. And after my consequential (but necessary) ratbag era that followed, I eventually opened up my heart again.

One beautiful day, I was at a coffee caravan surrounded by gardens, a local gathering place for kids, dogs and those looking to devour the best toasties in town. I was finishing up nannying with a family I’d been with for two years that day. Trying to wrangle a busy toddler while waiting for our croissant and babyccino, I ran into a very handsome guy I hadn’t seen for years.

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We knew each other previously in our hospo days but didn’t have much to do with each other back then. We briefly caught up on our lives before getting pulled away by a tiny human. He had to run to a work meeting, but I didn’t want to break his gaze. That evening, just after he discovered I was single, he bit the bullet and asked me out. I’m so glad he did.

The man I started seeing was like a breath of fresh air. He calmed my nervous system from the moment I was in his presence. He was older than me and had children from his first marriage, but it didn’t deter me from getting to know him more. The way he spoke, showed up and made an effort… it was everything I had been craving in my previous relationships, but was beginning to think didn’t exist.

After months of eye-opening experiences with typical fuckboys (thanks, Hinge), stage-five clingers and even a nice date with a woman, I finally felt like the universe had put me where I needed to be. I was ready to heal and feel loved again. But what’s a romantic comedy without a sad ending, right?

After eight weeks into our euphoric dating bubble, we had an unexpected realisation and a simple conversation left us feeling uneasy. He wasn’t isn’t sure if he wanted any more kids. I’d always wanted to be a mum one day. So, fuck.

When should I ask if they want children?

I confided in a good friend of mine one Sunday. We sipped our coffees and ate fruit toast as she let me voice my unfolding fears. As we spoke, I realised the emotional toll having relationships with men or women who are unsure if they want children can take. I began to question what my future might look like. The possibility of not being able to fulfil my innate desire to become a mother one day felt bloody terrifying.

While I’m not currently at a stage in my life where I’m ready for that chapter, the possibility of it not being an option taught me a valuable lesson: maybe it’s never too early to know what someone wants in life when you start dating in your thirties.

My friend’s advice? “Spare the heartache. If he is uncertain, it’s a big box to leave unticked if that’s something you’ve always wanted one day.” No advice has ever rung so true.

How do you express your wants and needs to new potential partners?

Initiating hard conversations is never easy, especially when we’re talking about wants, needs and expectations. But the truth is, you’re both going to benefit by knowing where the other person stands. I wholeheartedly believe that being ‘on the same page’ as someone else is a huge part of the reason why relationships flourish or flounder.

Finding myself in a situation like this, I always try and bring it back to the advice my mum gave me in the past: “Sometimes there’s so much connection between two people, it’s just about wrong timing.” I’m always so shocked at how intuitive my mother is, even if she isn’t meaning to be.

When should I take a break?

Now I’m at a crossroads, trying to understand what my heart wants compared to what it needs. We’re still seeing each other several times a week, and I still don’t know what I’m doing. But there are definitely feelings there, and it feels so easy to be in each other’s company.

I’ve taken the ‘let’s put this conversation on ice’ approach for now, but I’m hoping I might have a breakthrough this year. If 2023 taught me anything, it’s that with discomfort comes substantial growth.

I’m an avid listener of The Imperfects podcast and I recently caught up on an episode my friend told me was a “must-listen” (thanks, Treen). It was an episode with Gina Chick called ‘Don’t Fight Life’. I’m not sure if it was coincidental that I listened to it the day my love life was unravelling, but her message was timely. She said, “Be ok with the uncomfortable and honour the emotions in whatever mess it takes.” If it’s meant to be, it’ll find a way.

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