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The first message: how to start a conversation that goes somewhere

5 min read

The best profile in the world can't survive an opener of 'hey'. Not because 'hey' is offensive — because it hands the whole job of the conversation to the other person. First messages have one purpose: make replying easy and worth it.

Reply to the person, not the photos

Everything you need is in their prompts. They told you their ideal Sunday, their green flags, the thing they're learning. Pick the one that genuinely made you react and react to it: 'Crying at airport arrivals is elite behaviour, for the record' beats 'you're gorgeous' every single time — because only one of those could have been sent to anyone.

Ask the second question

The first question anyone asks about a prompt is obvious. The second one shows you actually thought about it. If their prompt says they make great negronis, everyone asks 'oh what's your secret?' — you could ask what they'd make for someone who hates gin. Specific beats smooth.

Give a hook back

A great opener is answerable. End somewhere they can pick up: an opinion to agree or fight with, a question with a real answer, a tiny confession that invites one back. 'I also organise my bookshelf by feeling — mine goes from spite to hope, left to right' gives them three things to reply to.

Length: two sentences, maybe three

One word says you didn't try. A paragraph says you tried too hard. Two or three sentences — one reaction, one question or hook — is the reply-rate sweet spot.

If they don't reply, it wasn't the message

Send one good opener. If it goes nowhere, send nothing else. A great message to the wrong person was always going to fail, and a follow-up never fixes it. The opener's job is to find the people who were going to be easy to talk to — with the right match, honestly, even 'hey' would have worked.

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