Put one true, mildly surprising fact about yourself in it and then stop. The slot works when she finishes reading and immediately wants to ask a follow-up, which a plain odd fact does and a punchline does not. Say the strange thing, do not explain it, and let her curiosity do the rest.
What the prompt is actually asking for
The wording invites a reveal. That is the whole design of it: you are meant to tell her something she would not have guessed.
Most men hear it as an invitation to be clever, which is a different task and a much harder one. Cleverness has to land in eight words with a stranger who is half paying attention, and when it misses there is no recovery. A true odd fact cannot miss in the same way. The worst case is that she finds it mildly interesting and moves on.
So aim for interesting rather than funny. Funny is a bonus if it arrives on its own.
The three answers she has already seen
Before writing yours, know what you are competing with, because the same handful come up constantly.
The negging joke, in all its forms. Anything shaped like "I'm actually taller in person". The self-deprecating throwaway that admits you have nothing: "I have no idea how to answer this". And the fake reveal that reveals nothing, the "I'm secretly a great cook" variety, which is a claim rather than a fact.
Each of those reads as a man who wanted to be finished with the box. She is not offended by any of them. She simply has nothing to say back, which costs you the slot.
Find your one true surprising fact
The answer is almost always somewhere in your history rather than in your personality.
Look at the odd jobs. Look at the year you lived somewhere unexpected. Look at the skill nobody guesses you have, the competition you once entered, the relative with an unusual life. Look at the thing you did once and never mention, because it never comes up.
"I used to gut fish for a living." "I can read music but not sight-read speech in my own second language." "I once spent a winter as the only person living in a ski resort." Every one of those makes a stranger want to ask a question, and none of them is a joke.
If nothing comes to mind, ask a friend what he tells people about you when you are not there. That answer is usually the one you should have used.
Say it plainly and stop
The most common way a good fact gets wasted is the sentence it arrives in.
Write it flat. No build-up, no "you would never believe this", no explanation of why it is interesting. The interest is in the fact, and framing it as interesting is the written version of laughing at your own line.
Then stop before the explanation. "I used to gut fish for a living" is finished. "I used to gut fish for a living, which taught me a lot about patience" is not a reveal any more, it is a lesson, and lessons close the door the reveal opened.
Why a joke usually costs you here
A joke has to be funnier than the twenty jokes she read before yours, and comedy in a single line is the hardest kind.
It also gives her nothing to do. Reading a good joke is a complete experience. She smiles, she finishes, and there is no unanswered question left to send you. A fact is incomplete on purpose, and incomplete is what gets replies.
There is a middle route if you want warmth in there. Tell the true odd fact and let the oddness itself carry the humor. "I have been bitten by the same neighbor's dog three separate times" is funny and is also a fact she can ask about. That combination beats either one alone.
Answers that work, and why
"What if I told you I have never seen a single Star Wars film and I do not intend to start." Works because it takes a position, which invites either agreement or a fight, and both are replies.
"What if I told you I built the shed in the third photo and it has not fallen down yet." Works because it points at something else on the page, which makes the whole thing read as one man rather than separate boxes.
"What if I told you my first job was reading the news on local radio." Works because it plants a picture of you doing something she cannot picture you doing, and she will want to hear the voice.
Each of those is short, true, unexplained, and ends on something she can pull.
Where this one sits in the rest of your page
One slot cannot carry a weak profile, and it is worth being clear about that before you spend an hour on a sentence.
This answer is the one that makes her smile and reach for the keyboard. It only ever gets read if the photos above it got her that far, and it only converts if the rest of what she reads agrees with it. A man whose images say nothing and whose other answers are blank does not get saved by one great line.
So write this one well, then go back and check the rest. The photos in order, each answer doing a different job, the whole page reading as one recognizable person. That is the work this slot is sitting on top of.
Written by Matthew Stevens, Co-Founder & Head Coach. More than half a decade coaching men across the US and worldwide.
Everything here comes out of real coaching work: the approaches, dates, texts and profiles we go through with the men we coach.