Why Some Types of Texting Actually Work Better
Estimated reading time: 4 minutes
I’ve written about what makes for a better conversation.
In this article, let’s zoom in on texting specifically — where so many conversations never get the chance to become conversations at all.
A lot of people think “good texting” means being witty, fast, charming, cool-but-not-too-cool. But the texting that tends to actually work keeps the momentum going and leads to real connection.
Let’s go over three common patterns of above-average texting conversations.
Be A Little Abrupt
There’s a funny thing that happens on dating apps: people are terrified of being abrupt, or random, or — God forbid — weird. Unfortunately, this fear does a fantastic job of making them sound generic and bland:
“How’s your week going?”
“How was your weekend?”
“How’s your day so far?”
While these questions are polite and harmless, they’ve become the new “Hi, how are you?”
So I recommend launching into a conversation. A few examples:
“So how do you feel about desserts? Scale of 0–10?”
“Thanksgiving is coming up — I’m already thinking about pumpkin pie. What about you?”
“Random question — are you a morning person or a night owl?”
Yes, they seem abrupt. But the trade-off is that they’re more engaging and interesting — which can very well make all the difference.
The point is you’re giving the other person something to actually respond to.
Be Specific
A lot of dead-end conversations happen because the opener is too broad.
“Tell me about yourself.”
“What do you like to do?”
“What are you up to today?”
Again, these are technically polite and harmless, but they force the other person to guess the scope of their answer — which ends up being too much work.
(Do I start from childhood? Do I list the errands I ran today? Are they asking if I’m free to meet up tonight?)
Cue the laws of physics…
If an opener has no direction, the conversation has no momentum. And the weaker the prompt, the weaker the response.
A specific prompt makes things easier — without needing to go deep or profound.
Compare two sets of examples:
Generic: “What do you do for fun?”
Specific: “You mentioned you like hiking — any favorite spots for someone who thinks they like hiking but secretly prefers flat ground?”
Or:
Generic: “What do you like to do?”
Specific: “Your profile says you’re into comedy — do you have a favorite special?”
Which one would you rather respond to?
Keep It Moving
Some texting goes nowhere because the conversation has the structural integrity of a wet napkin. It just folds in on itself.
“Hey”
“Hey :)”
“How’s your day?”
“Pretty good, you?”
“Not much, just relaxing.”
This is the texting equivalent of walking on a treadmill: technically movement, but you’re still in the exact same spot, staring at the same wall, wondering why nothing is changing.
When I say keep things moving, I don’t mean rushing into “Hi, coffee?”
I mean giving the exchange a little direction — a new thread, a small detail, literally anything other than reporting the hourly weather of your day.
A few examples:
Instead of: “How was your day?”
Try: “That thing you mentioned earlier — did it end up happening, or did the universe intervene?”
Instead of: “Not much, you?”
Try: “I just tried a new cafe and realized I ask for recommendations knowing full well I’ll order a black coffee.”
Instead of: whatever 1-2 word response
Try: “That reminds me — how did your family dinner go?”
And when things are going well, forward movement is just acknowledging it without making it weird:
“This is fun — want to keep chatting over coffee sometime?”
or
“I’d be down to chat on the phone for ten minutes this week if you’re interested.”
Forward movement is what turns two people tapping on screens into two people who might actually meet each other.
Closing Thoughts
Before assuming someone is boring, chaotic, dry, or “just bad at texting,” it’s worth taking a quick look at your own style.
Most people think their texting habits are perfectly normal. (Statistically impossible, but very human.)
Do you launch into something specific, or do you start broad and hope for the best?
Do you keep things moving, or do you accidentally walk the same small-talk treadmill?
Do you give the other person something to respond to, or are you handing them the conversational equivalent of a blank sheet of paper?
Successful texting does not necessarily need to be charming, witty, poetic, or profound.
It’s simply giving the conversation enough clarity and direction to go somewhere — anywhere — other than, “Not much, you?”
And once you can spot the difference, it becomes a lot easier to see who’s a mismatch… and who might actually be worth meeting.
