5 Things I Learned From Dating Older Women

If you’re someone in their twenties and you have the chance to date someone in their thirties, forties, even older, I urge you to seize it. Whether it stands the test of time or not is beside the point – and this isn’t about bragging rights either. Dating someone significantly older than yourself can be a hugely rewarding experience. It can serve as a gateway to thoughts and emotions you may dodge in other romantic relationships, thus making you a better romantic partner in the future. Here are some of the things I have learnt from my experiences.

1. Older People Are Cooler Than You

I was dragged into my first relationship with an older woman. We worked together and so she knew me pretty well.

We went to a bar after work and I was drunk. I was chatting up girls my own age. Regurgitating the same old spiel, telling rote jokes to little avail. After striking out again I found myself left alone in our booth. That’s when she kissed me.

Confidence is cool. So is living a life full of experiences. At her house were relics from her travels, photographs with people I hadn’t heard of – but sounded fascinating after being described. In a group photo she pointed out her ex-husband.

When we went out she was totally unaffected by the opinions of other people. She was so confident in herself – free of the anxiety of youth. Regardless of your particular definition, being yourself is cool. Once someone becomes truly mature they begin to mellow out, and in the past I frequently used to find myself envying older women’s insouciance.

Later, when we were lying in bed and I asked her why she had kissed me, she told me she hated who I was when I flirted with young girls.

‘But it works most of the time,’ I told her.

‘That’s not the point,’ she said, placing a hand on my cheek. ‘You’re better than that. Well, you can be.’

2. They Do Casual Better Than Anyone Else

Once you start becoming used to approaching older people, there is another, albeit minor benefit. In my experience, even if the person is not interested they’ve almost always been nice about it. Not necessarily flattered, but I’ve certainly rarely been laughed at or treated with condescension (whereas when approaching young girls… well).

If you can take things to the next level then you’ll find that a casual relationship with an older person is far superior to that with a young person. You may not even call it; more than once I’ve been told that the person didn’t want to date someone my age but of course we could have fun together.

As long as you’re mindful that this is likely to happen even if you like someone more than that, then you’ll find yourself in an effortless casual relationship.

With maturity comes a greater respect for emotion and other people’s time. I’ve never been cancelled on short notice by an older woman and the sex, even in casual relationships, usually reaches depths of passion which are not always reached with younger people until much further down the line.

Speaking of which…

3. The Sex Is Amazing

This isn’t to say you’ll never sex enjoy sex with a young person again, obviously. But that said, sleeping with older people can illuminate your sex life. Quite simply, with extensive practice comes superior results. More often than not an older partner will be much more attuned to your body’s needs and can adapt quickly to deliver what you want the most.

They’re also clear in what they want. Don’t be offended if you’re told what to do. Just trust your partner and go with the flow. Chances are they will show you something new that you’ll want to re-enact with your future sexual partners, regardless of their age.

4. You Can Be Completely Open (If You Want To Be)

Where sex lies in one hand, in the other lies the heart. Dating older people can be a hugely rewarding experience for those who want to express themselves but feel inhibited by social norms.

In my relationships with older women there’s always been a tolerance of self-expression that I’ve found quite rare in women my own age. Often when going out on a limb to say how I really feel about something, I can tell quite quickly that I’ve made the girl I’m with uncomfortable.

Yet with older women, when I’ve told them about a book or a movie that I was incredibly moved by, always I see their expression soften. Delighted that someone my age could express themselves freely without self-consciously inhibiting their behaviour, hoping to be seen certain kind of way. That confidence was something I learnt from these very experiences. An ability to speak without fear of rebuke or awkward, averted eyes.

5. They’ll Grant You Perspective Beyond Your Years

Almost every conversation I have with someone older reminds me of how little I know about the world.

When you’re in a relationship with an older person you get an insight into a life quite different from yours. That intimacy means you may have to shoulder the complaints of a man or woman who has far more outgoings payments than you; who has friends getting married or raising kids, whilst they are not. Becoming privy to the obstacles you’ll end up facing in your own life can be very sobering and grants perspective to those still in their youth.

They’ll also teach you to appreciate things you may overlook. Even the simplest of things.
For instance, I’ve always talked too much. I’m usually the kind of guy who opens his mouth before he thinks, predisposed to offer my own opinion before being asked for it. You may embellish these bad habits in relationships, the other person not wanting to say anything until it builds up to such a point that you end up arguing.

But the aforementioned clarity of mind, combined with life experience means that often older people can shine a light on your flaws without it being insulting.

Case in point: I was sitting with my girlfriend (twelve years my senior) in a pub garden. We were sitting on a bench at the waterside. Boats bobbing gently on the water. Inoffensive waves lapping at the sand. It reminded me of a film I liked where the main character sails off and waves to his friend, who is crying on the shoreline.

I wanted to tell her about the film. How I loved it as well as the director’s other work. In fact he’d made three films in my top ten. What are the chances of that? Or maybe I’m just biased. Should I be more tolerant of new filmmakers, or is it ok to just enjoy the things you like? It’s your life after all, right?

I drew in a deep breath, ready to unload this all.

‘You know this reminds-‘

‘Shhh,’ she breathed in a soft, tutelary tone. Her hand resting on mine.

She had not even turned to face me, yet it didn’t feel patronising. There was no ill-intent. Simply the calm reminder that that this was a moment to enjoy. A peaceful vignette that I should savour.

So I closed my mouth. I think I may have blushed with embarrassment. But soon my cheeks were cooled by the wind. The call of gulls passed overhead, retuning between one ear and the other. I feel the sting of salt water in my nostrils.

Then I smiled as we sat there in silence, looking out onto the water. TC mark


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