For Two Months, I Wined and Dined a 56-Year-Old Lady at England’s Finest Restaurants—But the Moment I Invited Her to My Place, She Instantly Dropped Her Act

For the past two months, Id been wining and dining a 56-year-old lady. But the moment I invited her round to mine, the mask dropped instantly.

Five years ago, I finalised a peaceful divorce and soon settled into the familiar routine of a bachelors life. Lately, though, coming back to an empty flat on my own started to feel a bit lonely.

Im 56, still in good health and not lacking in energy. I signed up to a dating website, hoping to find a woman to share life with. As luck would have it, in the very first days of chatting, I actually stumbled upon someone interesting.

Her profile was simple:

“Jane, 56, widow, seeking a decent man for a serious relationship.

Her photo showed a pleasant woman, nothing pretentious, with kind eyes. We got to chatting very quickly. Straightaway, I made it clear that I wasnt after a drawn-out virtual relationshipI wanted something real, someone to build a life with, travel together, share the everyday. She agreed, and we arranged to meet in central London that weekend.

Our first date went brilliantly. We wandered around for agesthe weather was glorious. She spoke enthusiastically about her job and grandchildren, and I listened attentively, nodding along. I liked that she was calm and didnt talk my ear off. Later, I took her to a cafémy treat, of course. Im a bit traditional: when a man invites a lady out, he pays.

And so began the usual wine and roses phase. I bought all the flowers and chocolates, but the enjoyment was mutual. Every Friday and Saturday we had our little cultural evenings. Im not tight-fisted, but looking back, if I tot up the costs of the last two months, it makes me wince a bit.

Wed go to the theatre and then on to a restaurant without fail. That was our weekly thingsome weeks itd be an exhibition, other times a concert, or a day out in the countryside followed by a hearty pub lunch.

I tried to be a proper gent, thinking we were growing closer week by week. Shed beam at me, slip her arm through mine in the street and say things like,

“David, its such a pleasure spending time with you, youre the perfect gentleman.”

Naturally, I was flattered.

Little warning signs at the cinema

Looking back now, her behaviour said it all.

For starters, not once did she invite me round to hers. Not for a cup of tea, not just to pop round. There was always a reason: “Oh, the flats a mess, or “Granddaughters staying over, or “Im absolutely exhausted from worklet’s just meet at the café instead. At first I put it down to nerves or feeling awkwardwomen on their own for a while might feel odd inviting a man into their home. I chose not to press her and simply waited for the moment.

Then there were the odd things shed say about age. When it came to fun, getaways, restaurants, she was young and livelykeen to plan trips and weekends away, or visit a water park. But as soon as Id try to move the relationship into a more personal or physical space, shed instantly turn into a strict, grumbling grandmother.

Once at the cinema, sitting on the back row, I gently put my hand on her kneejust resting there, nothing else. She immediately moved it away, firm but not unkind:

David, people will see.

But Jane, its dark, theres no one near us.

I dont care, it looks unseemly. Were not teenagers.

I put it down to a strict upbringing. Maybe she was genuinely chaste and I should respect those boundaries. Still, it started niggling at me. We werent sixteen, we were nearly sixty. Time isnt on our side; we havent got years to be offended or coy.

Another thingshe loved giving me full run-downs of her ailments. At our age, everyone gets a few aches or a dodgy back, nothing unusual. But she seemed to dwell on it, almost relishing her list of complaints. She could talk all evening about her back pain or which cholesterol tablets worked best.

I listened sympathetically, even offered to drive her to a good doctor. But the minute I mentioned my twice-a-week swimming to stay fit, she wrinkled her nose:

“Why do you bother with all that? Youll only wreck your heart. At our age, its better to relax on the sofa and read something worthwhile than splash about in chlorine.”

But slumping on a sofa had no appeal for meI wanted a full life.

The moment of truth and unexpected lectures about shame

Yesterday, I finally decided enough was enough. Two months of seeing each other is plenty of time to work out if you fit together.

We were having dinner in a lovely gastropub, enjoying steak and kidney pie and a very nice bottle of wine. We were in high spirits; she was laughing loudly and telling funny stories about her colleagues. I decided it was time for an honest chat.

After dinner, we got in my car. It was drizzling outside, the car was cosy and warm, the radio played softly. I gently took her hand and, for once, she didnt pull away.

Jane, do you fancy coming back to mine? Just for some tea, maybe some music?

She stiffened straight away, smile gone, face like stone.

David, what are you really getting at?

Im not hintingIm saying it clearly. I like you. Im free, youre free. Weve been seeing each other over two months. Naturally, Id like for us to get closer.

She launched into a speech about age, shame, and higher spiritual connection that floored me:

Are you listening to yourself? she said sternly. Thats for young peoplefor continuing the line. Why would we, at our age? The very thoughts absurd. Can you imagine how dreadful wed look without our clothes? My wrinkles, your bellygood grief! What matters now is a meeting of minds, supporting each other, real friendship. All youre thinking about is the animal part.

I sat there, genuinely taken aback. Was I some kind of beast just because, after eight weeks, I wanted a woman as a man would?

Jane, come on. What belly? I keep fit, everythings fine. You look amazing for your age. Why write yourself off so early? Who says life ends at fifty-six and all thats left is camaraderie?

Thats whats right and proper! she shot back. Respectable women my age look after the grandkids and do a bit of gardening. Id be ashamed if my family found out Id taken up with a man for that sort of thing.

At that point, I lost my patience and let out everything Id been holding in:

So you never wanted a man to actually share your life with! You enjoyed being wined and dined on my expense, theatre trips, drivesin my car, eating my gifts. No problem with that beast. But the minute I looked for proper closenesssuddenly, its disgusting.

She flushed, but more from anger than embarrassment.

What, so you expect me to fling myself into your arms in exchange for dinner?

Dont twist it, I said, managing to keep calm. I treated you well, and that expects some natural deepening of a relationship. All you wanted was a convenient friend with a fat wallet and a car.

She stormed out of the car, slamming the door behind her. I didnt go after herit was all pretty clear. I watched her march proudly to her building and felt strangely let down.

I love good conversation, books, and history. But Im a manwith normal feelingsand I refuse to pretend otherwise simply because some woman has built ironclad hang-ups around wrinkles and numbers.

I deleted her number and my dating profile. I need time to get my head straight after this circus.

Ive made up my mind: from now on, at the very first date, Ill be upfrontwhats your view on intimacy? If I get another lecture about old age and grandchildren as the meaning of life, we split the bill and I say goodbye.

What do you thinkam I out of order, or is it really so awful for a decent man to suggest intimacy at fifty-six? And why on earth do women like that even go on dating sites if they believe their times up?

Personal lesson: Ive learnt that its better to be honest about what I want from the very beginning, even if it makes things a bit awkward. It saves a lot of wasted time and emotional energy down the line.

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For Two Months, I Wined and Dined a 56-Year-Old Lady at England’s Finest Restaurants—But the Moment I Invited Her to My Place, She Instantly Dropped Her Act