DatingBy Bhupendra Singh Chauhan · Updated August 13, 2026
This is a storytelling question, and the story is really about you. What you choose to find funny, who you make the villain, and whether the whole thing lands somewhere. The answers that work put the writer at the centre of the comedy. The ones that fail make a stranger the punchline, and the reader immediately wonders how they would be described afterwards.
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I talked about my dissertation for forty minutes before noticing. She was extremely polite about it. I now have a rule that I am allowed one paragraph about work and then somebody else speaks.
Why it works: The writer is the problem and knows it, which is the safest and funniest way to answer this. The rule at the end shows something was learned without turning it into a lesson.
We ran out of things to say by the starter and then both ordered dessert out of sheer politeness. Ninety silent minutes. We still said we would do it again.
Why it works: No villain at all, just a recognisable social failure both people participated in. The dessert detail is the sort of specific that makes a story worth telling.
A very nice man took me to see a film he had already seen twice, then explained it. I have never been more certain about anything in my life.
Why it works: Keeps the other person likeable while still being clear about the mismatch. Deciding it was simply wrong rather than that he was awful is what keeps the answer generous.
She looked nothing like her photos, could not hold a conversation, and spent the whole time on her phone. Absolute disaster.
Why it falls flat: Three complaints about someone who cannot answer back. The reader learns how this person talks about dates that go badly, and quietly places themselves in that future story.
Honestly there have been so many bad ones I would not know where to start. Online dating is rough.
Why it falls flat: A complaint rather than a story. It answers the question by declining to pick one, and it opens with weariness, which is a difficult mood to make attractive.
He turned up twenty minutes late. Not the end of the world but not a great start.
Why it falls flat: Too mild to be a story. The question is offering a chance to be entertaining and this declines it, leaving the reader with nothing to laugh at or ask about.
Make yourself the comedy. A story where you were the awkward one is safe, funny and quietly flattering, because it shows you can laugh at yourself. A story where a stranger is the villain does the opposite — the reader is not thinking about your bad date, they are wondering how they would be described in six months. Keep one concrete detail so it feels like a real evening rather than a general complaint, and land it somewhere: a rule you made, a thing you now avoid, or simply that you both survived it politely.
Being the awkward one yourself. Self-directed comedy is safe and likeable, while a story where the other person is the villain makes readers wonder how they would be described after a bad date with you.
No. Every complaint about someone who cannot answer back tells the reader something about you rather than them, and the thing it tells them is not flattering, however deserved it might be.
Pick a different one. A profile cannot hold a distressing story well, and a stranger has no good way to respond to it. Save that for someone who has earned the context to hear it.
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