Only when you can name what you want that does not depend on their reply. If the message is meant to change how they feel about you, it usually deepens the loop. If it closes a practical loop, states a boundary, or asks one honest question you can live with either answer to, it is reasonable to send.

How long should I wait before texting an ex?

Long enough that you can read their last messages without your heart rate changing — for most people that is several weeks, not days. Waiting is not a tactic to make them miss you; it is how you get access to your own judgment again.

What should I not text an ex?

Avoid long explanatory messages, repeated apologies, tests disguised as small talk, and anything sent after midnight or after drinking. These read as pressure and almost always produce a shorter, colder reply than you hoped for.

Should I text my ex?

Short answer: text them only if you can name what you want from the message without needing a particular reply. Almost every message people later regret was written to change how the other person feels — and that is the one thing a text cannot do.

1. Name the real intent

Write the honest version of your goal in one sentence before writing the message. Most goals fall into four groups:

Closing a loop — returning belongings, settling logistics, ending ambiguity. Usually fine to send.
Stating something true — a boundary, an apology you owe regardless of response, a decision. Fine to send if you can send it once and stop.
Asking one real question — "do you want to try again?" — reasonable only if you can accept a no on the first reply.
Testing whether they still care — the "hey, how have you been?" that is really a probe. This is the category that hurts, because a lukewarm reply becomes new evidence to over-analyze for another week.

2. Use the evidence you already have

You are not guessing in the dark: the last two weeks of messages already show the pattern. Look for three things instead of re-reading the final text.

Effort symmetry — who started conversations, who lengthened them, who let them die.
Response to vulnerability — when you said something honest, did they move toward you, change the subject, or joke it away? This predicts what happens to your next honest message.
Repair attempts — did conflicts end in repair, or in silence that one of you eventually stepped over?

If vulnerability was consistently met with deflection, a new message will most likely be met with deflection too — with the added cost of the wait.

3. Three cases where reaching out usually backfires

You are in the acute spike. Days one to fourteen after a breakup, urgency feels like insight. It isn't. Nothing you send in that window says what you mean.
They ended it clearly and asked for space. Contact then reads as pressure, and pressure hardens a decision that ambiguity might have softened.
You have already sent an unanswered message. A second one moves the conversation from "should we talk?" to "how do I get them to stop?"

4. If you do send it

One message. Short. No history, no case-building, no list of what they did. Something you could read out loud without flinching, sent in daylight, sober, with your phone then put down. Length is the tell: long messages signal that you need something back.

Rule of thumb: if you would be ashamed to see the message quoted back to you in six months, it is not the message — it is the feeling wanting an exit.

5. What to do with the urge instead

The urge is real information: it usually points at an unfinished sentence in your own head, not at them. Write the message you would send if there were no consequences, do not send it, and read what you actually asked for. People often find they wanted acknowledgment, not reconciliation — and acknowledgment can come from elsewhere.

Where Subtext fits

Subtext reads the actual conversation — a WhatsApp export or a single screenshot — and shows the pattern across it: effort balance, how vulnerability was handled, recurring conflict loops, and what a draft message is likely to trigger before you send it. It is the difference between guessing about one text and seeing the dynamic it belongs to.

Analyze the conversation