how to keep a conversation going over text (without it feeling like work)
We’ve all been there - the conversation feels like it’s dragging on, you feel like you’re having the conversation because you need to.
The convo may have started well, but after some time, it felt a little less like getting to know her, and a little more like work.
I’m gonna hold your hand when I say this - asking “how was your day” is a terrible conversation continuer. But worry not, here are some tips you can use to think about your text convos differently, so it never runs dry.
1: instead of asking for information, ask for stories
Compare the following:
How was work?
vs:
What was the funniest thing that happened at work today?
How was lunch?
vs:
If you could only eat one thing for the rest of the week in your area, what would it be?
How was your weekend?
vs:
What was one part of your weekend you wish you could do again?
See the difference? One invites a short, descriptive answer - the latter invites some thought, which naturally flows into a conversation.
2: use what’s already in front of you
One of the easiest ways to keep a conversation flowing is to stop thinking about “new” topics. What you want to do instead is to pick up on something she’s mentioned, and ask more about it.
E.g. if she just told you “I just booked tickets to Japan!”
Instead of saying “Nice!” and then moving on, or stopping at “Which part?”, try asking something incredibly specific that you’re actually interested in. Like “Which snack are you going to overpack home?” or “How many Don Quijote runs are you expecting to make?”
Notice that this change comes from a place of genuine interest and curiosity - and should not be taken as a formula. Practise this with your friends, or anyone around you. If they bring up something, enquire in more depth - so you have conversations, not one-si
3: please stop asking chat
I obviously did my research before writing this and I learnt that loads of you are asking ChatGPT / Gemini / Claude “What are good conversation starters on Telegram that aren't 'how was your day'?” or “Give me a funny, non-boring reply to this message.”
Why are you doing that? That’s not you.
When you type back the AI message, sure maybe you get a favourable response from her. But does it sound like you? Will it sound like you if it goes well and you eventually meet her irl?
AI might be useful for ideas sometimes if you’re absolutely stuck. But practise #2 and soon you’ll find yourself needing it less and less. And above all, even if you use AI to outsource your thinking / guessing, please don’t use it to outsource your personality.
at the end of the day: remember why you’re texting
It’s probably not because you’re trying to become lifelong pen pals or something - you’re trying to decide whether you’d enjoy meeting in person.
Once the conversation feels comfortable, ask her out - that’s what the dating apps, the asking for her Tele @ is for. If you’re unsure when or how to do that, I’ve written a guide on how to ask a girl out.
what if she only ever replies with one word?
Then I think that tells you enough, doesn’t it?
If texting always feels like hard work, it isn’t usually because you “don’t know what to say”. More often than not, it’s because you’re overthinking every message, worrying about what she thinks about your every response.
That's something we work through together in my Dating Deep Dives, where we look beyond the text itself and into the confidence and communication behind it.
about the author
I'm Wan Ting, founder of portmanteau, a dating coach for men in Singapore.
I help good men like you stop guessing and build practical dating skills for serious relationships.
