After Four Months of Messaging, Agreed to Meet a 52-Year-Old Suitor – He Opened the Conversation with Five Complaints

After four months of witty messages, I finally agreed to meet my 52-year-old admirer who kicked things off with five complaints.

They say the anticipation makes the party sweeter than the party itself. In Carolines case, the suspense dragged on for nearly four months, morphing into what could only be described as a serial drama with daily instalments.

During this time, she learned Olivers tea preferences down to the exact teaspoon, memorized the names of his childhood mates, and even stopped raising an eyebrow at his habit of signing off every good morning with three ellipses.

Caroline was forty-five that delightful age when you turn up for a date not with butterflies in your stomach, but with the amused curiosity of an anthropologist. Lets see what specimen shows up this time, she mused while getting ready.

She belonged to that rare breed of women who could wear a plain cashmere jumper as if it were a royal gown, and possessed such sharp self-deprecation that awkward moments melted away.

The Bottle

Oliver, whod just turned fifty-two, seemed sensible, a tad witty, and, most alluring of all, genuinely reliable in his messages.

At our age, Caroline, he wrote in the twilight hours, people arent chasing fireworks. They want warmth someone who understands without words.

Without words is fine, Caroline chuckled, applying mascara. Just so the words that do get spoken dont make me bolt for the exit.

They arranged to meet at a snug little café with ambient lighting and the scent of cinnamon in the air. Caroline arrived on time poised, confident, and hopeful for a pleasant evening. She looked smashing.

Oliver ambled in five minutes later. In real life, he was a bit shorter than his photos suggested and had a gaze like hed just spotted a catastrophic spreadsheet error.

He plonked himself down, offered a brief smile, and a hello.

No compliment, no good to meet you.

Oliver scrutinised Caroline as if conducting an audit. Then he suggested ordering coffee and dessert consensus at last.

Caroline, he began, with the measured tone of a deputy headmaster addressing staff, Ive been analysing our correspondence. Nearly four months. Now that I see you in person, I think its best I lay out five important points straight away. I have five grievances.

Something inside her quietly clinked the sound of good mood shattering. Caroline rested her chin on her hand and nodded.

Five grievances? Intriguing. Hit me.

Oliver missed the irony and raised his index finger.

First: The Blue Dress Photo

In one of your photos the one in the blue dress your figure looked different. Today, youre more, er, sculpted. It could mislead a man. At our age, women ought to be a bit more forthright.

Caroline mentally snorted. Sculpted thats progress. Thank heavens he didnt say monumental.

Second: Response Time

You sometimes reply far too slowly. For example, three weeks ago I messaged you at 2:15pm and you didnt reply until 4:40pm. Men despise waiting. Its disrespectful.

I think I was in a meeting then Caroline began, but Oliver was already on to the next one.

Third: The Venue

Why are we here? This place is way too posh. I suggested somewhere more down-to-earth. Such a choice screams conspicuous consumption.

Caroline looked at her latte and fought the urge to pour it over Olivers head, but curiosity won.

Fourth: The Dress

Why wear such a dress? Were just here for coffee. Its too much for daytime, and the jewellery is unnecessary. A woman should draw men with her depth, not her sparkle. Im looking for substance, not a shop window.

Fifth: Independence

You picked the café yourself, you go on about doing things yourself. You dont let a bloke feel like a man. I need a woman who seeks advice rather than flaunting independence. If were together, youll need to reconsider your behaviour.

He finished and folded his arms, seemingly expecting confession or grateful applause for his frankness.

Caroline looked at him and suddenly realised: Four months of banter had masked a meticulous manipulator. Seeking warmth? Hardly. He was after a compliant ego-booster.

You know, Oliver, she said gently, almost affectionately, Ive done some analysing myself. Took me five minutes to reach a conclusion.

And? Oliver squinted suspiciously.

Youre a marvel. You travelled across town just to present an invoice to a woman youve only just met for her taste, looks, and right to exist. Thats impressive bravado.

Oliver scowled.

Im just being honest.

No, Caroline shook her head, Youre not honest just hopeless, and trying to measure the world with a wonky ruler. Dont like my photos? Go to a museum the exhibits dont change. My reply speed bothers you? Get a Tamagotchi. Dont like the dress? I wore it for myself, not for you.

She stood, straightened her handbag, and looked him in the eye.

And one more thing. If your ego collapses at the word myself, you need more than romance you need rehab. At forty-five, I value my time too much to spend it on someone kicking off acquaintance with a performance review of my flaws.

Where are you going? And the coffee? Oliver muttered.

You can finish the coffee yourself. Itll help you save resources. One parting tip: if you want someone always staring into your mouth, book a dentist appointment.

Back home, Caroline promptly blocked Oliver on every platform. At her age, comfort isnt just a throw and silence, but also a phone free from people trying to wedge you into their misshapen template.

What do you think bungled flirting, or a well-rehearsed monologue? And really, is it worth pursuing, if from the first minute youre presented with a bill for simply being yourself?

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After Four Months of Messaging, Agreed to Meet a 52-Year-Old Suitor – He Opened the Conversation with Five Complaints