The five love lessons I've learnt dating again in my fifties

Independent

13-02-2025

Every now and then, while I was married, a single friend would come over and describe the hell of the dating apps. It didn't look like hell. It looked like enormous fun: a smorgasbord of single men, all of whom were looking for their partners. How much easier than when I was last single, when you had to go to a party and pray that there might be someone there who you fancied and – if the gods were smiling – hope they might fancy you too. Or, you'd hope a friend might offer to set you up on a blind date.
My smug married self would sit next to those single friends on the sofa as they speedily swiped left. 'Stop, stop. Wait! He looked so nice,' I'd shout while they mercilessly swiped left. 'Ugh,' they'd reply, continuing to swipe, only ever occasionally swiping right.
Mostly though, as fun as it looked, I was enormously relieved I didn't have to be out there. The thought of having to tell my stories again, get to know someone, play those dreadful games and go through all that insecurity and fear was horrifying.
I was single at the same time Helen Fielding was in the Nineties. As she was dreaming up her Bridget Jones Diary, which first appeared as a column in The Independent, I was writing about all my crazy dating mishaps in newspapers, which were followed by a book about being single in your thirties, living in London.
I wrote about what it was really like dealing with all the terrible men, falling madly in love only to get your heart broken over and over. I wrote about the boozy parties, and waking up next to the man whose face had blown up during the night because he didn't tell you he was allergic to cats.
At the time we were said to have created a new genre in literature, one that was dubbed 'chick lit'. Before then, women's fiction had been glitz and glamour, Jackie Collins and Judith Krantz. No one was writing about single women in a realistic, emotionally honest and funny way. I honestly thought I was going to be single for years, but wonder of wonders, I found someone, and ended up, as Bridget would say, as a smug married.
I was also relieved. And this relief only grew as I grew older. Who else would embrace this middle-aged body other than my husband? He knew this body before midlife, when it was still relatively firm. He knew this body when it was regularly waxed, and shaved, when varicose veins were something that happened to someone else. I shuddered in horror at the prospect of revealing this body to anyone other than him. Thank god, I thought, surveying the winter hair on my legs that I swore kept me warm during those cold months, I would never have to go through that again.
Except here I am, at 56 years old, with four grown children who have flown the nest, and suddenly single after the long three-year rough patch. After a year of being alone, I'm starting to dip a toe back into dating waters, and it is a terrifyingly different world from the last time I found myself out there, 25 years ago.
My first instinct was to run away. Which, dear reader, I did, to Marrakech. One of the benefits of my job is that I can work from anywhere and I wasn't looking for a relationship. I just wanted to meet new people. I felt completely liberated, freed from the old-fashioned notion that you have to be married in order to be happy.
After all, I'd been married. It hadn't made me happy. I decided I was not destined to be a wife. Perhaps I was instead destined to be a great friend, to have great friends. Single Jane in her 'Bridget years' was always up for an adventure, she lived her life in pursuit of fun. I was not so much fun during my marriage, and now single again maybe this was second-time-around fun Jane. I was going to be this bohemian free spirit, floating around the globe having more adventures, even if they weren't the romantic kind.
Except after a while, I started to crave.... romance; touch; someone to look forward to, not just something. And so, I entered my midlife dating era.
I crafted a profile. I wrote a list of things I love: crisp white sheets. Anita Pallenberg. Gratitude. Early Rolling Stones. Fiction. Cats. Kitchen suppers. Gardening. Dim Sum. Good manners. I hoped I sounded a little quirky, slightly unusual. FUN. The next day I woke up to an inbox filled with likes. One stood out. Handsome, 10 years younger, a twinkle in his eye. A landscape gardener, he lived in London, but after a couple of video calls, suggested we meet in Lisbon, to 'spend a little time together.'
It sounded fun. Until it wasn't.
We met. We had a fantastic evening, fuelled by much alcohol, flirting and laughter. I had forgotten what it was like to feel this kind of attraction. The problem started the next morning when we actually spent time together, without the balm of alcohol. We had nothing in common, and worse, by the end of day two, clearly didn't even like each other very much.
I didn't yet understand how many men use the apps as an unofficial escort agency. Soon after that, I matched with Joseph, a handsome tech guy who wanted to meet up, telling me he particularly liked parading his women around in their very, very short, tight dresses. My writerly curiosity was piqued. I quizzed him mercilessly about how this situation worked. At the end of the night, he said he would buy the women whatever they wanted.
'Is this like Pretty Woman?' I asked. 'Do you take them shopping?'
'God, no.' He said. 'I hate shopping. I give them cash.'
I paused. 'Tell me something, Joseph. Do you ever pay for sex workers?'
He was horrified. 'I would never do that.'
I put down the phone.
Then there was a two-month text conversation that was interesting and lively, and ended with the man concerned arriving in Marrakech, with his children. He refused to have a video or phone call saying it was more fun to keep the mystery until he arrived. We met for drinks. Nothing about him said successful entrepreneur, well-travelled, erudite and clever, all the things he had claimed to be.
Things took a different turn when he confessed he was into dominating and asked if I was ready to 'embark on this journey together'. The bill came, he disappeared to the bathroom. I paid and never saw him again, aware that I was breaking the golden Bridget Jones rule: 'I will not fall for any of the following: alcoholics, workaholics, commitment phobics, people with girlfriends or wives, misogynists, megalomanics, chauvinists, emotional f***wits or freeloaders, perverts.
Then there was Archie, a former officer, who was handsome and charming (v v good). But did I want to wake up to pictures of him in his underpants? No. I did not (Why do middle-aged men think any of us want to see their ageing bodies in greying not-quite-tighty whities? Ugh!).
I was starting to feel like a dating drudge, and worse, entirely disposable. A nice conversation starts, and abruptly ends. Or, mid-conversation, they disappear without warning. You sometimes do the same. The other night I was having what seemed to be a great chat with a neurosurgeon on his way back from the ballet. We had moved to WhatsApp, but when I let slip my thoughts about Trump (v v bad). I was immediately blocked.
Hinge has the type of men I might run into at a dinner party, but none of them ever like me. Eharmony is the Primark of the dating apps. Raya – the fancy celebrity one – waitlisted me. Bumble has the most hits, but mostly from twentysomethings. Babygirl may be a fantasy for some, but, in reality, I'm not into a romance with someone who reminds me of my children.
And yet, there is always the triumph of hope over experience. So I have decided to look at being single as a learning experience. Lesson one: understanding I am a classic people-pleaser, who quashed my needs for my husband's, causing resentments to build.
Lesson two: learn how to say no. Lesson three: gym pics, boat pics, T-shirt vest things, anything mentioning a Sunday roast, is a hard no. Lesson four: Do not put up with bad behaviour. Lesson Five: call it out when it happens without fear of pushback
I am ashamed to say that it has taken me over 50 years to learn these lessons.
I now have a new life here in Marrakech, and regularly fly back and forth to the UK to see my family. I have a circle of friends, both very old in London, and very new in Morocco, who fill my life with joy.
And so I am adjusting to being alone, which is not always v good, but is often v marvellous. Adjusting to being single, at my age and stage, truly feels like the hardest thing I have ever done in my life. But I am learning that my friendships will keep me buoyed. I am learning that perhaps I am more resilient than I ever knew. I am learning not to be mad about the boy, and to value myself instead. Which is perhaps the most important lesson of all. So hello new single life, time to start a new chapter…