Because "hey what's up" costs you nothing, says nothing and could have gone to forty women, and a woman with options gets that exact text every week. The cocky version is worse. A line built to sound like you don't care tells her you spent time deciding how to sound like you don't care. She reads low effort at best and a nervous man in a costume at worst, and she lost interest before the second line.

What the cocky text is trying to say

Most of these texts are borrowed from a rulebook. The rulebook says a high-status man is slow, short and a little smug, so the man copies the surface. He sends two words and waits a few hours on purpose. He adds a teasing line like "wow, are you friendzoning me?" to show he is relaxed.

The surface is easy to copy. The thing underneath is not. A man who really is busy and wanted is short with his phone because his day is full. A man who is acting short is staring at the screen waiting for a reply. She cannot see the screen, but she can feel the difference in what arrives.

What a woman with options reads instead

Picture a woman who has men writing to her all day. She is not scoring your text against a perfect one. She is scanning for one thing: does this man know me, or is he running a play?

"Hey what's up" fails that scan at once. It has nothing of her in it. A line like "you're alright, I'll let you see me soon" fails it harder. Telling a woman you are in no rush is a strange thing to announce, and a man who feels the need to announce it is usually in a rush. Another line accuses her of friendzoning you before anything has happened. That looks like effort pretending to be play.

None of these make her angry. They make her lose interest, and she moves to the next text without replying.

Why acting uninterested backfires

My point about texting is that the same behavior can be strong or weak depending on where it comes from. Fast replies, long replies and formal replies are weak when they come from eagerness. Slow, short, casual replies are strong when they come from a man with a full life.

The trouble is that the cocky text is the second behavior produced by the first feeling. Eagerness dressed as indifference. She can usually tell, because the content gives it away. A man who truly does not care does not write a line whose only job is to prove he does not care.

The better move is to stop performing the attitude and build the life that produces it. Then your texts come out short and relaxed without any effort, because you have things to do.

What to do instead

Three things separate a text she answers from one she skips.

  • It has something of hers in it. Her pitch on Thursday, the trip she mentioned, the dog she said hates the rain.
  • It is short and casual. One idea, written the way you would say it, with no stack of questions and no essay.
  • It points toward a plan. The text exists to move you from the phone to a table.

Compare "hey what's up" with "Good luck with the pitch today. Tell me how it goes." The second one took ten seconds longer and says she is a person to you. Then, a few texts later, "Thursday works if you want that wine bar you mentioned" gives her something easy to say yes to.

Do not wait a set number of hours before answering. A rule like that breaks your own plans and kills the flow when she is excited. Answer when you have seen it and have something good to say.

The text is downstream of the meeting

Here is the part most men skip. How a text lands depends on how she felt when she met you.

If you spoke to her in person and she enjoyed it, a short casual text reads as warm and assured. The same words from a stranger she matched with online read as lazy. In the first case she already has a picture of you from your voice, your eye contact and how you handled the moment. In the second the text is the whole picture, so every word carries too much weight.

That is why men who meet women face to face tend to text better without trying. The attraction was built in the conversation, and the text only has to confirm a plan. Texting should be the small formality that follows a good interaction. If you ask your texts to create the attraction from nothing, they will fail.

So the long fix is practice at approaching and holding a conversation until you do not need a clever text to carry you.

When "hey what's up" is fine

Context decides. If she gave you her number an hour ago, laughed through the whole conversation and told you to text her, a quick "hey, good meeting you, are you free Thursday?" works. So does plain "hey" to a woman you have already dated twice. She already likes you, and the greeting is just a greeting.

The cocky versions are not wrong because of the words. They are wrong when they are the only thing you have, sent to a woman who does not know you yet, in place of a reason for her to answer.

A quick test before you send

Read the text and ask three things.

  1. Could this have been sent to anyone? If so, add something only she would recognize.
  2. Would I say this to her face? If you would feel silly, so will she.
  3. Does it move toward meeting? If it does not, cut it or add the plan.

If a text passes all three, send it and put the phone away. The best thing you can do after sending is go be busy.