How casual should my first text to my ex actually be?
Short answer: Your first text back should be one short, low-key sentence, nothing warmer than a casual "hey, it's been a while, how've you been." No exclamation points, no emoji, no explaining how you feel. Every extra word reads as pressure instead of confidence. Match or land slightly under their energy in the reply that follows.
The draft sitting in your notes app is almost certainly too long. Not because the words are wrong, but because a first text after silence should barely cost you anything to send: one plain line, nothing to defend, nothing to explain.
I’m Benny Lichtenwalner, breakup coach and author of How to Get Your Ex Back. When clients bring me their draft, it’s nearly always too warm, too funny, or too eager, and the fix is the same every time: cut it down until there’s nothing left to trim.
Why does a short, flat text work better than a warm one?
Someone reading a message from an ex isn’t just reading the words. They’re reading what the effort behind it says about where you’re at. A long, colorful, enthusiastic message says you’ve been waiting for this moment. A short, plain one says you’re doing fine and this is one small thing among many.
That second read is the one that keeps a conversation open instead of shutting it down. Warmth you haven’t earned back yet reads as pressure, even when it’s meant kindly. And every extra sentence spends something you can’t get back: the sense that you’re a little bit unknown again, not a fully open book.
What should the actual message say?
Keep it to one observation or a plain greeting. “Hey, it’s been a while. How’ve you been?” is a complete message. Don’t add a second sentence explaining why you’re reaching out, and don’t apologize for the silence.
| If they reply with… | Send back… |
|---|---|
| A short, low-effort answer | Something equally short. Don’t fill the gap. |
| A warm or enthusiastic answer | Match the warmth, don’t exceed it. |
| Something logistical | A logistical, no-frills reply. |
| A compliment | A plain thank-you at the same register, nothing bigger. |
What’s the trim checklist before I hit send?
- Cut any “just kidding” or qualifier tacked onto the end.
- Remove emoji, unless the exchange is already playful, and then only one.
- Drop the period at the end of a short casual line. It reads as stiffer, and slightly annoyed, than you mean it to.
- Cut anything that sounds like you composed it rather than just said it.
- If it’s longer than two sentences, you’ve written too much. Cut it to one.
What kills a good opening message?
Over-empathizing is its own separate mistake, distinct from writing too much. Something like “that’s rough, I know how much that mattered to you” sounds caring, but it signals you’re managing their feelings, which is its own form of trying too hard. A plain “that’s rough” does the same job with none of the weight.
Stacking your good news the same way: if you’ve had a decent month, mention one thing, not three. Listing accomplishments reads as trying to prove something, even when that’s not the intent.
What this looks like in practice
A composite of two clients, details changed. One spent an evening drafting and redrafting a re-entry text, worried that anything short would look cold. What she sent, after cutting three drafts down to one line, was eleven words. The reply came back within the hour, warmer than she expected.
Another kept adding a line explaining he’d been thinking about the relationship, convinced the plain version left too much unsaid. Once he cut it entirely and sent the short version instead, the conversation actually continued past a single exchange for the first time in weeks.
How does this change once we’re actually talking again?
The flat, minimal tone matters most right at the start, in the first message and the exchanges right after it. Once a real back-and-forth is running, you can warm up, gradually, staying a notch below their energy rather than jumping ahead of it. The goal was never to stay cold forever. It’s to stop the first message from doing the one thing that kills a re-entry before it starts: showing up too big, too soon.
For the full re-entry sequence and what comes after the first reply, the re-entry message guide has the complete protocol.
Related questions
Is it okay to use an emoji in my first text to my ex?
One, at most, and only if the exchange is already playful by the time you send it. A first message is not the place. Save it for a reply once there's an actual back-and-forth going.
Should I explain why I'm reaching out now?
No. An explanation turns one casual line into a conversation about the relationship before either of you is ready for it. Say the plain thing and let the reply tell you where things stand.
What if my ex replies with something warm? Can I match that energy?
Match it, don't exceed it. If they say something kind, a plain "thanks, hope you're doing well too" covers it. Going bigger than what they sent reads as relief, and relief reads as need.
How do I know if my text is too long?
If it's more than two sentences, it's too long. Read it back and cut anything that sounds composed: qualifiers like "just kidding," a period at the end of a short line, more than one thing you did that week. One plain sentence is the whole message.
Does this still apply once we're actually talking again regularly?
Less so. The flat, minimal tone matters most in the first message and the first few exchanges, when you're still re-establishing contact. Once a real conversation is going, you can warm up gradually, in step with them.