My previous dating history leans heavily towards older women, too. It was never a premeditated decision – I didn’t wake up one day and think, ‘I’m going to exclusively date women who have seen more general elections than I have’. It was just an organic process. The more I engaged with different women, the more I realised I connected best with those who had already been there and done that.
There is something about a woman who is past the age of uncertainty. She’s no longer figuring out what she wants, she already knows. She doesn’t play games, doesn’t do the exhausting push and pull away, and doesn’t live for validation. That is intoxicating to me.
‘I don’t have to worry about a ticking biological clock’
Most of the women I’ve been with have been professionals, lawyers, corporate executives or business owners. The age gap has varied; some were five years older, others 13. I don’t have a magic number, but I seem to gravitate towards women in their late 30s to early 40s.
Society has a funny way of resisting what it doesn’t understand. I’ve had friends jokingly ask if I have “mummy issues”. I have heard whispers about me being a “boy toy” or just another young man enjoying the ride until the woman realises I can’t give her what an older man would. Luckily, I don’t live for public opinion.
Still, the financial dynamic has been interesting. Some earned significantly more than I did at the time, which, as a man, forces you to check your ego at the door. You either embrace it or let it eat you alive. There were moments I found difficult, like gifts I wasn’t sure how to receive graciously, and dinners where a partner insisted on paying, where I had to remind myself that my worth isn’t tied to who picks up the bill. That was a learning curve for me.
There have even been subtle power struggles over finances, at times. Some older women have a nurturer’s instinct, and while that’s great, it has sometimes manifested in a way that made me feel I was being kept. I once had a girlfriend, nine years older than me, who would book trips, make dinner reservations, and send money “just in case”. It was well-intentioned, but after a while, it made me question my role: Was I her partner or just a well-dressed accessory?
But there are so many upsides to dating older women. Generally, they bring emotional intelligence, depth and an unparalleled sense of clarity. They don’t need you, and that makes the relationship so much more genuine. They’re not with you because of pressure, ticking biological clocks or societal expectations. They’re with you because they want to be.
As for what I give them – I’ve been told it’s a mix of stability and excitement. Many men their own age either take them for granted, or operate on outdated assumptions about gender roles. I have had women tell me they feel “seen” with me in a way they haven’t experienced before. Maybe it is because I don’t expect them to be caregivers or passive supporters. I want a partner, not a shadow.
‘Women my age often look for approval on social media’
A few times, I have dated younger women. It’s not that it didn’t work out because they were younger, but I found many were still in the phase of figuring themselves out. The conversations felt different. There was often a need for external validation, social media approval, the desire to be seen at the right places with the right people. I felt more like a participant in their journey rather than an equal partner.
The idea men must be older is rooted in a time when women’s survival depended on men. Older men had resources, stability and influence, qualities women needed for security. But today, women build their own wealth, own property, and shape industries. They don’t need an older man to take care of them.
What they do need is connection, companionship and intellectual stimulation. And if they find that in a younger man, why should that be a problem?
Of course, the big issue is the biological clock. Annabel has voiced concerns about time catching up with her. We are not using contraceptives, and while we have not put pressure on the idea of children, it is a conversation that lingers. I have made peace with whatever direction life takes us in.
Whether we have children or not, our bond isn’t contingent on that. I think men need to redefine their idea of legacy. Having children is great, but the depth and impact of your relationship should extend beyond reproduction.
I think younger men are realising fulfilment in a relationship does not come from outdated power dynamics but from mutual respect, emotional security and genuine compatibility. I don’t date older women because it is trendy, I do it because, for me, it works. And I hope more people learn to prioritise connection over convention.
