'Someone actually booed me in street.' What it's like dating a 35-year-old at 55.

One busy GrandPrix weekend at closing time I was stuck at a tram stop for ages unable to fit in any of the trams as everyone began to leave the big event.

After the fourth tram frustratingly zipped by like a giant sardine can the next one rolled in. The doors opened, and I realised I still couldn’t fit with everyone banked up against the doors.

One guy helped get the others to kindly make way for me, although I was thinking there was no way I’d really fit comfortably, but they’d been so kind to make way for me I couldn’t say no.

Watch: Dating according to your horoscope. Post continues below.

Video by Mamamia

This meant I was travelling along in the tram without a proper hold of the stabilising bars in my high heels, pressed against a bunch of people (all men), and pretty embarrassed about falling into them constantly as the tram wobbled and jolted along.

One of the guys was smoking hot, with an incredible body in his tight-fitting Grand Prix branded sports shirt. Talk about awkward, right? I kept apologising profusely for falling into his very buffed self – I am blushing just thinking about this.

The chemistry was in the air between us. Eventually, the crowd dispersed and I stepped back into my more appropriate personal space. From there, we struck up a conversation.

As I reached my stop and started to say my goodbyes, I realised he was getting out at the same stop. I was thinking, ‘Wow, what a coincidence’, although later I learned he only got out to ask me out.

So, that was the way we met and our first date was booked in. It was only later that I realised our age difference was bigger than I thought, much bigger.

I was 51 and he was 31 – a 20 year age gap.

Despite that, we’re still in each other’s lives four years on.

This wasn’t my first younger man actually and I thought I was going to be giving them up for good but here he was.

I was certain he was 10 years older and I often get mistaken for being 10 years younger.

I’ve been challenged by my own ideas of what’s an appropriate age to date. I had this idea that 10 years younger was acceptable but anything more wasn’t and put a ban on seeing anyone under that. Why is it that an arbitrary number matters at the end of the day anyway?


Society seems to have a set of invisible rules about what is okay and what is not.

I’ve been to places with a guy I was seeing and I’d encounter extreme reactions all in the one night, from people winking at me across the way in a ‘you go girl!’ kind of way, but also been booed (out loud!) with disapproval too.

Sometimes I’ve struggled with my own sense of ageing and felt especially old next to that six-pack body when I’m starting to get a little more ‘Renaissance’ style as the years have rolled by.

I do have a lot of younger friends, but older ones too. From 30s to 65 in fact. I don’t seem to see age like others do, I see the person.

I see their energy, what they care about, the spirit and values they hold.

I tend to connect with ambitious entrepreneurs who are keen to change the world somehow and they come in all ages and stages.

At first I had girlfriends prodding me and telling me how much some younger guys were hitting on me and I admit I was oblivious. Because they were so much younger it didn’t even cross my mind.

Eventually, I had a day where I said to myself “I wonder…” and decided to stop resisting and see what came of it. Yep… they were hitting on me! I embraced it even and attended speed dating events.

One was called ‘Toy Boy’ (hmm, the political activist in me wouldn’t really approve of that name now) but the concept was good.

No Mr-Right-Now was there that night, but it was a fun process to go through.

Same with apps like Tinder or RSVP – if you just open up the age range it is surprising what comes your way.

Is it problematic that Leonardo DiCaprio won’t date women his own age? Post continues below. 

Some common themes I hear are that men at least 10 years younger hate the pressure of women their age trying to lock them down into marriage and families.

I hear they find that generation obsessed with cosmetics and fashion and unimportant things but also wrapped up in a lack of self-confidence.

Confident younger men seem to find confident older women attractive in my world.

Real-life is where the magic happens though, like with Mr. Tram Guy. The chemistry between people is undeniable, and yet we do deny ourselves because of certain constraints that society puts up as barriers.

I meet people in the funniest of locations like the queue at the art gallery, at a charity lunch, the dancefloor, work events, at a supplier’s work kitchen… I think the key is in seeing the real person behind whatever the mask is that society paints of each other and accepting people for who they are.

I get that word ‘Cougar’ a lot, eww. Sometimes it comes with a ‘wink and a nod’ type thing and other times it is disdainfully meant.


I hate the idea of being a predator. I’d never approach a man of any age let alone hunt anyone down like a wild cat. Like Mr Tram guy, men in my life need to have the self-confidence to step out and ask me out or they won’t get to first base with me.

I’m pretty independent, driven, entrepreneurial and ambitious even. I don’t see myself ever living a traditional married existence ever again. For over 15 years I’ve lived independently now. I can do what I want when I want and with whoever I want. That’s intoxicating and quite empowering, and I don’t fancy giving that up in a hurry.

Sometimes I’ll watch an older man and younger woman walk down the street as if it is totally normal and completely invisible to everyone around them, yet for me it seems the stares are quite uncomfortable.

I do actually tend to spend a lot more time dating behind closed doors. Note to self – stuff what people think.

I do have friends who also have younger men in their life. Although I see some other friends who look at us as if it is a phase we’re going through and assume the relationship must be all sex and no substance.

They can’t imagine having a deep connection between generations, which really is just ageist.

The one thing I think about now is whether the person I am with is adding anything to my life or not. If they are, then why would I stop seeing them regardless of the age, stage, what job they do, how much money they have, where they live, what their interests are…any of that.

I think as a society we are all taught to think about the lifetime ahead of us and the pressure is intense; too much for many of us.

The result of this is a lot of people are in relationships that they’re not so happy about anymore but feel obligated, like a possession, and stuck.

A lot of us judge each other as unworthy of keeping for a lifetime and discard some good people too.

I do think about a time when I’m 70 and a partner is 50, and that doesn’t seem like it would work, but most marriages don’t make it that far either, so what am I worrying about?!

If I think about my life with anyone I choose to have in it for just one more week, one more year, or even one more decade if there is still good chemistry between us then that’s a gift I’m grateful for.

When the time comes to close things off and move onto a new chapter we can be grateful, thank each other and change the way we have each other in our lives. We can even remain friends and potentially even support each other with our next partners too.

I’d rather look at any relationship as a meaningful success story than a fairy tale that failed. Maybe the world needs to have more fun and lighten up? I’m having fun, anyway!

Feature Image: Supplied.

00:00 / ???