Why Conversations Fizzle Right After Matching
Estimated reading time: 4 minutes
I wrote about what makes for a better conversation.
In this article, let’s address texting specifically.
You send a message that feels like a light tennis (or pickleball, if you prefer) serve: “Hey, how’s your day going?”
They respond with an essay replete with emojis, side tangents, and a three-point reflection on the nature of... everything.
Or they respond cool, calm, and mysterious: “Good.”
You stare at the screen, overwhelmed in the first scenario, disappointed in the second.
Welcome to modern courtship — the great texting mismatch, where conversations often fall flat before they even begin.
It’s Not Me, It’s You
If you’ve spent any time on dating apps, you’ve probably felt the same frustration from multiple directions.
When they make no effort, it feels like pulling teeth.
When they write too much, it’s like being trapped in a digital monologue.
When they take what feels like forever to respond, your patience turns into apathy or suspicion.
When you don’t know what to say, every attempted response sounds either too lame or too desperate.
My guess is most of us have been on all sides of this — the over-writer, the under-writer, the hesitant responder, the one waiting for the “…” bubble.
The irony? Everyone thinks they’re the normal one.
How Texting Styles Clash
Texting seems simple, but it reveals personality differences almost instantly.
On the extreme ends:
Some people treat it like a tool — efficient and productive.
Others treat it like a space — a place to build rapport, find connection, and see if there’s potential.
Put those two in a text conversation and sparks rarely fly.
One person’s “direct” feels like another’s “rude.”
One person’s “chatty” feels like another’s “too much.”
One way isn’t necessarily right or wrong, per se — these are just two texting approaches that clash.
Mismatched Rhythms
Beneath every short or long reply are invisible habits and quirks:
How comfortable someone is with ambiguity
How fast they process social nuance
How much reassurance they need
Whether they think out loud or keep things brief
Two people can be equally interested, but if their rhythm doesn’t match, the conversation stalls. Like trying to dance when one person’s hearing jazz and the other’s hearing techno.
Okay, What Now?
Once you realize everyone’s playing by different texting rules, what do you actually do about it?
Do you adapt, or wait for someone who naturally matches your pace?
Do you treat texting as a filter, a warm-up, or just a mildly annoying step before meeting?
It might help to start by examining your own habits and attitudes:
What kind of texter are you? (Oftentimes, this mirrors how you prefer other people to text, too.)
Do you ask for a date right away?
Do you have whole conversations over text?
Do you tend to initiate — or rely on the other person to initiate — conversations, story-sharing, phone calls, or meeting plans?
Lastly — regardless of your style — how successful is your approach in terms of feeling understood, understanding others, or progressing connections?
I’ll get into what types of texting tend to be more successful in the next article. For now, it’s enough to realize your frustration might be less about “dating apps are the worst” and more about differences in texting styles.
