Embrace The Gentle Art Of Dating Yourself

There comes a point in midlife when life begins to shift. Children grow up and fly the nest. Careers plateau or pivot. Relationships change, sometimes ending, sometimes settling into companionship. And in these in-between spaces, many women find themselves with time they never used to have, and with it, a subtle but pressing question: what now?

For many, the instinct is to look outward; toward new relationships, new commitments or new ways to fill the gaps. But there’s another option, one that is less about seeking and more about savouring: the practice of “dating yourself.” At first glance, it might sound indulgent, even a little lonely. Who goes to dinner on their own? Who buys a single theatre ticket? Who books a holiday without a companion by the other side? But perhaps the better question is: why not? After all, learning to enjoy your own company isn’t just empowering; it is essential.

Here's what I've learnt: sitting at a restaurant table alone, you become deeply aware of your surroundings. You notice the flicker of candlelight, the laughter around you, the texture of the food you’ve ordered without compromise or negotiation. In the theatre, you find yourself absorbed in the story, not glancing sideways to check someone else’s reaction. Travelling solo, you set the pace and places that reflect your own interests and not as someone’s mum, partner, colleague or friend.

There is also a freedom in choosing yourself. Midlife is often marked by decades of putting others first. Family schedules, work demands and the needs of others leaves little room for your own desires. Dating yourself flips that script. It gives you permission to prioritise what you want and honour your own curiosity.

The benefits go far beyond the immediate pleasure of a good meal or an inspiring show. Taking yourself on dates builds confidence. Each time you walk into a café or stroll through a gallery alone, you strengthen the muscle of independence. You prove to yourself that you are capable of enjoying life without needing someone else to validate the experience. That confidence seeps into other areas - work, friendships, relationships -because you know you can stand on your own two feet.

Of course, dating yourself doesn’t mean shutting others out. It simply means you don’t wait for a partner or friend to be available before trying that new restaurant or visiting that exhibition. You become the person who creates experiences for yourself. And yes, it can feel uncomfortable at first but think of it as an act of rebellion against the idea that a woman’s life is only complete when shared. A reminder that companionship is lovely but not required and that joy can be self-generated.

So the next time you feel the itch for something new, resist the urge to wait for company. Buy the ticket. Order the glass of wine. Wander the gallery. Take the trip. And when you do, you may just find that the most enduring relationship of your midlife years is the one you cultivate with yourself.