How to Text

How to start a text conversation

The first message sets the tone and determines whether the conversation actually goes anywhere. Here's what makes a good opener — and why most first messages don't work.

Why most opening texts fail

The most common openers — "hey," "what's up," "how are you" — fail because they put all the work on the other person. They have to come up with something to say, and if they're busy or not in the mood, the easiest thing is to not reply.

Good openers give the other person something to respond to. They're easy to engage with.

What makes a good opening text

A good first message does one or more of these things:

  • References something specific to them or your relationship
  • Shares something (a link, observation, update) they can react to
  • Asks a question they can answer without thinking too hard
  • Is light and low-pressure enough that replying feels easy

Good opening text examples

Specific reference
Saw [thing related to them] and immediately thought of you.
Just remembered [shared thing] — how have you been since then?
Whatever happened with [thing they mentioned last time]?
Share something
You'd love this — [link/recommendation]. Made me think of you.
Found this and had to send it to you.
Easy question
What are you up to this weekend?
Have you [watched/read/tried] [thing] yet?
How's [specific thing in their life] going?
Direct and honest
Hey — been thinking about you. How are things?
I keep meaning to text you. What's been going on?

The "hey" problem

"Hey" alone is almost never enough. It signals that you want to talk but doesn't give the other person anything to work with. If you're going to open with hey, attach something to it immediately — a question, an observation, a share.

Tips for starting conversations

  • Be specific — generic messages get generic responses
  • Give them something to react to, not just a door to open
  • Keep the opener short — you can say more once you're in a conversation
  • The more you know about someone, the easier it is to start a conversation with them specifically
  • Don't overthink it. An imperfect message sent is worth more than a perfect message unsent.
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Worth knowing about
Starting conversations gets easier when you know what's going on in someone's life
Phonebook AI keeps notes on the people you care about — so when you go to text someone, you have something real to reference instead of defaulting to a generic opener.
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