For two months, I wined and dined a 56-year-old lady at restaurants. But the moment I suggested she come over to mine, she immediately dropped the act.
Five years ago, I had a smooth divorce, and since then, Ive grown quite comfortable as a bachelor. Lately though, I find coming home to an empty flat is starting to feel a bit lonely.
Im 56 and, touch wood, my health is still decent and Im full of energy. So, I signed up for a dating website, hoping to meet a woman for a proper partnership. And, as luck would have it, just a few days into chatting, I actually came across someone really interesting.
Her profile was straightforward:
“Margaret, 56, widowed, looking for a decent gentleman for a serious relationship.”
Her photo showed a lovely, down-to-earth woman with a kind face. Our messages quickly got going. I was upfront and told her I wasnt looking to faff about online for months I wanted a real relationship, someone to share day-to-day life and holidays with. She agreed, and we arranged to meet up that coming weekend in central London.
Our first date went brilliantly. We walked for ages the weather was gorgeous. She chatted away about her work and grandkids, while I listened, nodding along. I liked that she was calm and not one to talk over people. Afterwards, I invited her for a coffee. I insisted on paying its just how I was brought up; if a man invites, he pays.
And there began the classic wine and roses phase. I dutifully brought the flowers and boxes of chocolates, but both of us enjoyed the outings. Every Friday and Saturday, wed have cultural evenings: the theatre, a nice dinner sometimes an art exhibition, sometimes a concert, even the odd trip out of London for a pub lunch in the countryside.
I tried my best to be a gentleman; it felt like we were drawing closer. Shed smile sweetly, link my arm as we walked, and say things like:
“Michael, its such a pleasure spending time with you. Youre a proper gentleman.”
Of course, I lapped it up.
But looking back, a few red flags popped up early on.
First, she never once invited me round to hers. Not even for a cup of tea. She always had an excuse: the house was a mess, her granddaughter was staying, or she was too knackered after work and suggested we meet in a café instead. At first, I thought she was just shy a single woman might not be used to having a man in her space. So I didnt press it.
Second, her attitude to age was a bit odd. When it came to going out, taking trips, or dining at restaurants, she was young and eager, always suggesting new places to visit or weekends away. But the moment I tried to get a bit closer, anything remotely physical, shed suddenly turn into a grumpy old nan.
There was one time in the cinema, on the back row, where I gently put my hand on her knee. Nothing dodgy, mind you just my palm. She moved it away quite sharply, but politely:
“Michael, people are watching!”
“But, Marg, its dark in here, theres no one near us.”
“Doesnt matter, its improper. Were not teenagers.”
I put it down to strict upbringing. Maybe she was genuinely old-fashioned and her boundaries needed respecting. But still, I started to feel awkward. Were not sixteen, and at nearly sixty, you do start to wonder how much time you have to waste playing coy.
She had this habit of elaborating on her ailments. At our age, most people have a creaky back or a bit of blood pressure its normal. But Margaret would go into every detail, comparing blood pressure tablets and complaining about her joints through the whole meal.
I always listened, showed concern, and even offered to take her to a good doctor. But as soon as Id mention that I swim twice a week to stay fit, shed sniff and say,
“Whats the point of all that exertion? Youll just ruin your heart. At our age we should be curled up on the sofa with a good book, not swimming in chlorine.”
But thats the thing I have absolutely no interest in being a couch potato. I want to live life to the fullest.
The crunch moment came last night, when I thought, thats enough no more pretense. Two months is plenty of time to work out if were right for each other.
We were at a lovely place in Kensington, tucking into a brilliant meal lamb shank, a decent bottle of Rioja, the works. She was laughing, telling stories about her old colleagues, and everything felt perfectly normal. I genuinely thought, this is a proper woman, time for an honest chat.
Afterwards, we sat in my car. It was drizzling, warm and cosy inside, with some chilled music on the stereo. I held her hand, and this time she didnt pull away.
“So, Marg, shall we go back to mine? Put the kettle on, listen to some music?”
Suddenly, she tensed up, plastered on a fake smile and stiffened right up.
“Michael, what exactly are you suggesting here?”
“Im not suggesting, Im saying it directly. I like you, were both single, and weve been seeing each other for two months. Its only natural to want to be closer.”
And then she launched into this whole speech about age, propriety, and spiritual connection that left my jaw on the floor:
“Can you hear yourself? Thats for the young, for starting families. Why do we need it? Just imagine how awful wed look undressed! Ive got lumps and bumps, youve got a belly. Ugh! Its all about deeper connections and supporting each other. Youre just thinking about the animal side of it.”
I sat there, gobsmacked. So, apparently, Im nothing but a lech because after eight weeks of nice dinners and theatre visits I fancied her?
“Marg, come on. What belly? I go to the gym, Im in good shape. And you look fantastic for your age. Why are you writing yourself off? Who says life stops at fifty-six and were supposed to just sit and talk about the past?”
She snapped back,
“Its just whats done! Decent women my age mind their grandchildren and do the gardening, not go off with men for that sort of thing. Id be mortified if my kids found out Id taken up with a man like that.”
At this point, Id had enough and said everything Id been holding in:
“So you never wanted a real partner! Two months, you ate out at my expense, got lifts in my car, and all those shows and outings. No shame taking things from this animal then, eh? But as soon as I want normal intimacy, its yuck.”
She went red, but out of anger, not embarrassment.
“You think I owe you something because of dinner and concerts?”
“Dont twist it,” I replied as calmly as I could. “I treated you with respect, and with that comes the hope the relationship progresses. Youre just looking for a handy friend with a wallet and a car.”
She was out of the car like a shot, slamming the door as she went. I just watched her stomp off up the path, feeling disappointed with myself, really.
I love a good conversation, books and history. But Im still very much alive, with ordinary desires, and Im not about to give that up because someones locked into their hang-ups about wrinkles and age.
I deleted her number, and took my dating profile offline. Im going to need a bit of time to get over this farce.
Ive made up my mind now: from the very first date, Ill ask straightforwardly about intimacy. And if I get another lecture about being old and living for the grandkids, thats my cue to split the bill and say goodbye.
So, what do you think was I out of line suggesting intimacy at fifty-six? Or is it really such an outrageous insult to a decent woman at our age? And why do women like that even bother with online dating if theyve already decided their time for all that has passed?







