Before you text an old friend, read your last exchange. You may find a conversation that simply trailed off, a question you never answered, or a plan that never quite became a visit. How you left things gives you a place to begin.
A few messages you could actually send
If something reminded you of them, tell them what it was. Suppose you pass a restaurant where you used to meet:
“I walked past our old lunch place today. They still have that enormous menu. It made me think of you. How have you been?”
Choose a detail you would both remember fondly. The message gives them something familiar to respond to, even if a lot has changed since you last spoke.
You can also get in touch simply because you miss talking to someone:
“Hey, I was thinking about you today. It’s been a while. How have you been?”
You can tell them more about your own life once you know they have time to talk.
If their last message is still sitting unanswered, acknowledge that before changing the subject:
“I realized I never answered your message about the move. I’m sorry I let it sit. How are you settling in?”
If they asked you a question that still matters, answer it. Returning with a cheerful hello while skipping over what they said can leave the same unfinished conversation between you.
When you owe more than a hello
If you missed an important occasion, broke a promise, or disappeared when they needed you, name what happened. A vague apology for “being bad at texting” may leave them wondering whether you understand why they were hurt.
You might write: “You asked me to call after your appointment, and I didn’t follow through. I’m sorry I wasn’t there when I said I would be.” Explain what happened if it helps them understand, while keeping the apology clear about your part.
They may want to discuss it, or they may not be ready to pick things up again. You can acknowledge what happened without asking them to reassure you that everything is fine. If they have asked you not to contact them, respect that request.
Find out what life is like now
If they reply, ask about the things they tell you. Someone you knew well can have a very different life by now. You can hear about their new job or an interest they’ve taken up without covering everything that’s happened since you last spoke.
“What’s been keeping you busy lately?” leaves more room than assuming they’re still in the job or relationship you remember. Share something current about yourself, too, so they have something to ask you about.
If you enjoy catching up, you could suggest a time for a call. Or you might exchange a few messages and leave it there for now, glad to have heard how the other person is doing.
If you don’t hear back
If they don’t reply, you may wonder whether sending the message was a mistake. You don’t know yet why they haven’t answered. Check that you used a current number if you have a reason to doubt it, and give them time.
One later follow-up can make sense if you think the message was missed: “I’d still enjoy catching up when you have a chance.” Repeated messages asking whether you did something wrong give them another thing to respond to. After a follow-up, leave the next move with them.