How to Not Be Boring Over Text
If you're getting a lot of 'lol' and 'haha' replies and the conversation keeps dying, the problem usually isn't that you're an uninteresting person. It's that you're texting like you're filling out a form. Let's fix that.
Why Texts Go Flat
Most boring texts ask questions that can be answered in one word. 'How was your day?' gets 'good.' 'Did you have fun?' gets 'yeah.' You've created a job interview, and nobody wants to stay in that conversation. The other issue is pure summary texting, where you just report facts about your life with nothing for the other person to grab onto.
Give Them Something to Work With
Every text you send should have a loose thread they can pull. That means adding a detail, an opinion, or a reaction, not just a fact. Instead of 'I'm watching a movie tonight,' try 'I'm watching that new thriller everyone's recommending and I already know I'm going to be annoyed by the ending.' Now they have three things they can respond to. That's not a trick, that's just how good conversation works in any format.
Ask Specific Questions, Not General Ones
General questions feel like small talk. Specific questions feel like genuine curiosity. 'What did you do this weekend?' is forgettable. 'You mentioned wanting to try that new ramen place, did that actually happen?' shows you were paying attention and gives them something real to talk about. Pay attention to what they've told you before and reference it. That alone will put you ahead of most people they're texting.
Stop Over-Explaining and Start Reacting
Boring texts often have too many words and too little personality. You don't need to write a paragraph justifying why you liked a restaurant. A short, genuine reaction lands better. 'That place was way better than I expected, the kind of meal where you're sad when it's over' says more about you than a full review would. Personality shows up in how you react to things, not in how thoroughly you describe them.
Use Callbacks
A callback is when you reference something from earlier in the conversation or from a previous conversation. It creates an inside-joke feeling and signals that you're actually present, not just going through the motions. If they mentioned last week that they hate mornings and you text them at 8am, lead with 'sorry for texting at what I know is an ungodly hour for you.' Small thing. Big effect.
Match the Energy Without Mirroring It Blindly
If they're sending short, punchy texts, a wall of paragraphs back is going to feel like a lot. If they're being playful, meet them there. This isn't about shrinking yourself. It's about reading the room. The goal is a conversation that feels easy, not one where it seems like one person is doing all the work.
The One Thing That Fixes Almost Everything
Be more specific about your own life. Vague texts get vague responses. Here's a concrete example: instead of texting 'had a weird day,' try 'had a weird day, my coworker brought in a fish-based lunch and now the whole office smells like a harbor.' That's a real detail. It's visual. It has a point of view. The other person can laugh, commiserate, or ask a follow-up. You've handed them something real to respond to instead of a blank wall.
What Not to Do
- Don't rely on 'wyd' or 'hbu' to start conversations. Those put all the work on them.
- Don't send a question immediately after they just answered one. It starts to feel like an interrogation.
- Don't perform interesting. Trying to sound witty in every single text is exhausting to receive. Just be direct and specific.
Being interesting over text is less about being clever and more about being present. Show up with a point of view, pay attention to what they say, and give them real things to respond to. That's it.
Paste your actual conversation below and Hank will give you the honest read on where it's going flat.