The word people use is desperate. What they usually mean is: I cannot tell how this is going to land, and I will not find out until it is too late to change it.
That is a solvable problem. The word is not.
Free to try. We never store your chats.
People rewrite a message 6 times to make it shorter and send something that still reads exactly the way they were afraid of. Length is not the thing being measured on the other end.
Warmth does not read as desperate. Wanting something does not read as desperate. What reads that way is a message asking for reassurance while pretending to ask something else.
1. The follow-up that takes back the first one. You send something honest, he does not answer in 20 minutes, and you send a second message that softens it. The second one is what he reads first, and it tells him the first one was not steady.
2. A question with no answer in it. "Are we okay" and "did I do something" cannot be answered well over text. They hand him your evening, and you both feel the handover.
3. Explaining. 1 line of context is context. 4 lines of context is an argument with someone who has not said anything yet.
Most of the time the first draft is the honest one and the 5th is the managed one. The managed one lands worse — not because it is polished, but because he can hear the managing in it.
If you are going to change something, change 1 thing: cut the part that is asking him to tell you it is fine. Keep the part that says what you actually mean.
This is the part that helps and almost nobody does, because there is nowhere to do it. Your friends have heard it 4 times and have started answering as your friend rather than as him. Your own head is not neutral either — at 1am your anxiety plays his part, and it plays it badly.
What you want is to hear it back in his register. Not what a reasonable person would say. What he, specifically, tends to say when someone comes at him this way.
There is a real risk here worth naming. Run the same sentence 40 times and you will deliver it like a line you learned, and people can hear that. Prepared and memorised read differently, and in a relationship the second one is worse.
So the thing to walk away with is not the sentence. It is knowing where he gets defensive, what he does when you raise it directly, and which of your 2 openings he actually answers. Then you say it in your own words, once.
Waiting 3 days does not make you less desperate. It makes you 3 days more invested and no clearer, and the message you send on day 3 usually carries all 3 days in it.
How long to wait depends on what is open between you. It has never depended on a number.
Paste the thread, then say the thing you are afraid to send. It answers as him — built from how he actually texts in that thread, not from a general idea of men.
You find out where it goes wrong before it goes wrong. Then it writes the version you would actually send, and tells you whether tonight is the night to send it.
Try it on your conversation