October 9, 2026

He Asked Me What My Five-Year Plan Was Before the Olives Arrived

A Tuesday first date in Clapham, a list of terrible opening lines, and the small mercy of a friend with a fake emergency

Tuesday, 11.40pm, on the Sofa With My Shoes Still On

I am home. I am fine. I have eaten half a packet of crackers standing at the counter, which is what I do after a bad date in the way other people have a cigarette.

For the record, his name was Jonty and he works in “strategy.” I never did find out for whom. We matched nine days ago. His profile had a photograph of him holding a fish, which I let slide, because every third man in London is holding a fish and you cannot rule them all out.

We met at a gastropub in Clapham of the kind that has a chalkboard, a dog and a burger costing nineteen pounds. I got there first. He arrived six minutes late, said “you’re shorter than I expected,” and sat down.

The Five-Year Plan

The olives had not arrived. I want to be clear about the timeline. We had ordered a drink each and a small bowl of olives, and the waiter had not yet come back, when Jonty leaned forward, put his elbows on the table and said: “So. Where do you see yourself in five years?”

I said, “At this rate, still waiting for olives.”

He did not laugh. He said it was a serious question, because he was “dating intentionally” and did not want to waste either of our time. He then told me his own five-year plan, which involved a house in Surrey, two children and a dog called something like Monty. It was all very detailed. There was a spare room. At no point did the plan appear to require a particular woman. It had a vacancy.

Not Alone

On the Northern line home I looked for comfort and found it. The London Prat has a piece, an old favourite of mine, on cringeworthy things men actually said on first dates. It opens with a scene I could have written tonight: a dimly lit gastropub, two people who matched on Hinge four days ago, overpriced lagers, and the dawning sense of a catastrophic error of judgement.

It then gives fifteen lines. I will not repeat them all. One man opens by asking how his date feels about burping. Another has a theory about shampoo. The article says these lines deserve a blue plaque, and I agree. Somewhere in Clapham there should be one that reads: “Here, in 2026, a man asked for a five-year plan before the olives.”

What I love about that piece is that none of it is exaggerated. That is the horror. Any woman who has dated in this city for more than a year could add three of her own.

Why They Say These Things

I have a theory. I have had a lot of time to develop it.

The man who says something appalling in the first ten minutes is not, usually, a bad man. He is a nervous one who has read something. A podcast told him to “be direct.” A friend told him women like confidence. A forum told him to “screen” early. So he arrives with a script and delivers it like a hostage reading a statement.

Jonty did not want to know my five-year plan. He wanted to have asked. It was a box he had been told to tick.

The ones I worry about are not the nervous ones. They are the smooth ones, who say all the right things in exactly the right order. Give me a burping enthusiast any day. At least you know where you are.

The Rescue

My friend Dee and I have a system. At forty-five minutes she texts: “How’s the patient?” If I reply with a thumbs up, she leaves me to it. If I reply with a tortoise, she rings with an emergency.

Tonight I sent the tortoise at thirty-eight minutes. She rang. I said “Oh no. The whole ceiling?” loud enough to be heard. Jonty looked concerned. I said my flatmate had a leak and I would have to go.

He said, “That’s a shame. I thought we had real alignment.”

Alignment. Like wheels.

What I Am Actually Looking For

Since he asked, and since I had a long Tube ride to think about it. In five years I would like to be laughing at the same things as someone. I would like him to be able to sit in a silence without filling it with a question from a list. I would like the olives to arrive and both of us to be glad about the olives.

That is not a plan. You cannot put it on a slide. But it is what I am after, and no amount of intentional dating is going to find it by interview.

A Small Defence of the Bad Date

I will say this for evenings like tonight. They are never wasted. A good date is lovely and you tell nobody. A bad date is a gift to everyone you know. I have already sent the five-year-plan line to four people, and Dee has asked permission to use it at work.

The Prat understands this. Half of what it publishes under British satirical news on first dates and London satirical news about gastropubs is just the city’s bad evenings, written down properly. I gather Bohiney Magazine does the same for American women, who have further to drive home afterwards.

Wednesday, 7.50am

He has texted. “Great to meet you! Hope the ceiling’s OK. Would love to continue the conversation.”

The conversation. The one about the spare room.

I have replied that the ceiling is being looked at and that I do not think we are aligned. He sent back a thumbs up. No tortoise required.

I have taken my shoes off now.

SOURCE: https://bohiney.com/

The London Prat
Vivienne Pratfall