What Stories to Tell on a Date: The Inventory Exercise, the Three That Work, and the Three That Don’t
You do not have no stories. You have a hundred and have never written them down, so they are not there when the pause comes. The exercise that finds them, the three kinds that work early and the three that don’t.
The stories to tell on a date are the ones you already have and have never filed: the worst job, the time you were confidently wrong, the thing you did alone, the small disaster that ended well. The inventory exercise below surfaces them with ten prompts. Then the filter: the three kinds that work on a first date are the small disaster, the honest failure with a line, and the thing you care about more than you should; the three that don’t are the ex, the triumph, and the trauma. Each story gets the thirty-second shape from how to tell a story: setup, turn, line, hand-back.
On this page
The inventory, then the filter
Write one line for each. Not the story; the line that reminds you of it. Ten lines, ten minutes, and you have an inventory most men never make.
- The worst job you ever had, and the day it was worst.
- The time you were completely, confidently wrong about something and found out in public.
- The thing you did alone that you have never explained to anyone.
- A small disaster (a train, a kayak, a wedding, a kitchen) that ended fine.
- The hobby or subject you care about more than is reasonable, and the moment you realised.
- A person who changed your mind about something, and what they said.
- The strangest thing a stranger has ever said to you.
- The plan that went wrong in a way that was better than the plan.
- The thing your family does that you thought was normal until you were twenty.
- The best meal, the worst haircut, the longest walk, the time you got lost: any one of them.
- The filter: three that work early, three that don’t
- Works: the small disaster. The kayak, the wrong train, the wedding speech. It makes you the person things happen to, it has a built-in turn, and it hands back easily (“tell me you have one”).
- Works: the honest failure with a line. The time you were confidently wrong. It shows you can laugh at yourself, which is most of what people mean by charm, and it is the opposite of a brag.
- Works: the thing you care about too much. The lighthouse documentary, the supermarket league table. Passion in a small subject is more attractive than competence in a large one, and it gives her something to tease.
- Doesn’t: the ex. Any story in which an ex is a character. It makes her the audience for your last relationship.
- Doesn’t: the triumph. The promotion, the marathon, the deal. It is a brag with a plot, and talking about yourself has why.
- Doesn’t: the trauma. The real thing, the hard year. It may be the most important story you have, and the first date is the wrong room for it. How much to share has when.
- Pick three from the inventory that pass the filter and give each the four-part shape: setup in a sentence, turn, line, hand-back. Say them out loud once, to yourself, so they have a shape and not a script.
- Tell one on the next date, when something she says brings it up. Not as a set piece; as a reaction. A story told because the conversation went near it lands twice as well as one told because you had it ready.
- Add to the inventory weekly. One line for anything that happens that would make a friend laugh. In a month you will stop running out of things to say, which is the real reason this page exists.
“Any good stories?”, two ways
A first date. She has asked what he has been up to lately.
A triumph, then a second triumph, delivered as news. Both true, both fine, and neither is a story: no turn, no line, nothing for her to do but congratulate him. She asked a polite follow-up because there was nothing else to ask.
He has told her he is doing well. She has learned nothing about what he is like.
Same date, same question.
The same half marathon, told as the failure it also was: setup in a sentence, the turn (the rhino), the line (he has the rhino’s time written down), and a hand-back she took immediately. He has told her nothing about his fitness and everything about what he is like.
The Spice Girls story is better than the rhino. That is the inventory working.
What makes stories fail on a date
- Having none ready because you never wrote them down. The inventory is ten minutes and it is the whole fix.
- Telling the triumph. It is a brag with a plot. If the half marathon is the story, the rhino is the line, not the PB.
- Telling the ex. She becomes the audience for a relationship she was not in.
- Telling the trauma early. The first date is for finding out whether there will be a third. Save the real things for the room that can hold them.
- Telling it as a set piece. A story that arrives regardless of what she said is a recital. Wait for the conversation to go near it.
- Three in a row. One story earns one of hers. The Conversation Balance.
You are not short of stories; you are short of an inventory
Men who say they have no stories have had the same number of things happen to them as everyone else. What they lack is the file: a list of ten lines, each one a reminder, so that when the conversation goes near the kayak the kayak is there. The filter keeps the file useful (small disasters and honest failures early, the real things later) and the shape keeps each one thirty seconds. Do the exercise once and the pause on a date stops being a blank, because there is somewhere to reach. Running out of things to say is the diagnostic; this page is cause two’s fix.
Go deeper: The Conversation Balance: How to Not Sound Like an Interviewer When Talking to a Girl
Questions
What are good stories to tell on a first date?
Small disasters that ended fine, honest failures with a line in them, and the thing you care about more than is reasonable. They make you the person things happen to, they show you can laugh at yourself, and they hand back easily. The inventory exercise above finds the ones you already have.
What stories should I avoid on a date?
Any with an ex in it, which makes her the audience for your last relationship; the triumph, which is a brag with a plot; and the hard real thing, which deserves a room that can hold it rather than a first drink. All three are fine stories; they are the wrong room.
What if I genuinely have no interesting stories?
You have the same number as everyone else and no file. Do the ten prompts, one line each, ten minutes. The worst job, the time you were confidently wrong, the small disaster. Then give three of them the four-part shape. The problem was never the stories; it was that they were not there when the pause came.
How do I bring a story into a conversation naturally?
Wait for the conversation to go near it, and tell it as a reaction to what she said rather than as a set piece. “That reminds me of…” is fine; so is just starting at the turn. A story told because she mentioned running lands twice as well as the same story told because it was ready. How to tell a story has the shape.
