Messaging on OkCupid is free. You have to Like a woman before you can message her, and once you Like each other, you can send each other messages from your messaging page. If she has not Liked you yet, you can send one introductory message, called an Intro, so she sees your full profile and your message at the same time.
You Like first, then you write
OkCupid wants conversations to be between people who are interested in each other. So it makes you Like someone before you can message her.
Once you and another member Like each other, you can message back and forth from your messaging page. That is the ordinary route and it costs nothing.
The Intro: one message before she has Liked you
An Intro is a single first message you can send to someone you have Liked, before she has Liked you. She sees your full profile and your Intro at the same time.
The Intro goes to her Intros tab. If she Likes you back, it moves to the Conversations page for both of you, and the conversation continues from there.
That has a practical meaning. Your Intro is your one shot to start the chat before she has said anything. You do not get to send three in a row.
What happens to your messages
Two rules around storage are worth knowing.
Free members can hold a large number of messages on the Conversations page, and paid members have unlimited space. For most men the cap is never a problem. If you reach it, clear old conversations that went nowhere.
Messages are also automatically deleted after some months. A conversation that is old enough will disappear from your page, so do not rely on OkCupid as an archive. If a conversation matters, move it somewhere better: swap numbers and take it to a call.
If an Intro seems to have vanished, OkCupid has a help page on why an Intro message can disappear. It is worth a look before you assume a woman deleted you.
What a good Intro does
An Intro lands in a list. A woman who has an Intros tab full of messages is skimming. So what you write has to be easy to answer and clearly written for her.
A line that works looks like this: it mentions one specific thing from her page and asks a question she can answer in a sentence. "You wrote that you are learning to surf badly. How bad, and is there a story?" gives her something to say, and it shows you read her page.
A line that does not work is "hey" or "how is your day". It could have been sent to anyone, and she can tell.
Keep it short. Two or three sentences is enough. Leave out your life story, your job title and any compliment about her body.
After she answers
Once she replies, the work is not to keep the conversation going forever. It is to turn it into a plan.
Keep matching her energy. If she writes two lines, write two lines. If she asks you something, answer it and ask one back. After a handful of exchanges, suggest a specific drink: "I know a good place on the east side. Thursday evening work for you?"
If she is not ready, she will tell you, and the way you handle that matters. Answer in one friendly line and move on.
When she does not reply
Many Intros are not answered. That is not a message about you. It is a numbers fact on every app, and women ignore far more men than they answer.
Do not send a second message to the same woman straight away, and do not ask why she has not replied. If you want to follow up, wait a few days, and only once.
What you can control is the quality of what you send. If your Intros are not getting answered, read three of them out loud as if you were the woman. Do they sound like they were written for her? If not, rewrite them to be about one real thing on her page.
A two-week check
Count your Intros sent, replies received, conversations that lasted beyond a few messages and plans made. If replies are low, the first line needs work. If replies are fine and plans are missing, ask for a specific drink sooner. If almost nothing comes back, look at your photos and your written section, since a woman reads those before she reads your message.
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.