What makes it hard to reach out?

Nobody decides to lose a friend. The thread goes quiet, the quiet goes unnoticed, and one day someone you loved is someone you used to know.

I am building something about that. Clarence is a private Mac app that notices who you’re drifting from and drafts the message to bring them back. Your messages stay on your Mac. It never sends anything by itself.

I am one person, and these answers come to me, not to a company. Before I build any more of it I want to know whether I have the problem right, or whether it is a version of it only I have.

16 questions, which I know is a lot. Most are one tap, so about three minutes, and every one is optional. Answers save as you go, so you can stop whenever you like and the ones you gave still count. The longer version of why.

The problem 1 of 16

Is there someone you have lost touch with?

Someone you have been meaning to message and have not.

2 of 16

How long has it been?

3 of 16

How did it happen?

4 of 16

What actually stops you sending something?

Pick as many as are true.

5 of 16

If you tried to write that message right now, how would it go?

6 of 16

How many people is this true of?

Roughly. Nobody has counted.

7 of 16

Have you ever tried to fix this?

A reminder, a list, a note to self, anything.

8 of 16

When did you last actually message someone you had lost touch with?

9 of 16

When you do reach out, how does it go?

Pick as many as are true. It is rarely just one.

A few things about you 10 of 16

Do you text people from your Mac computer?

11 of 16

Would you let it read that conversation?

Here is how it would work. Clarence reads your recent iMessages with that one person, on your Mac, so it can see what the two of you last talked about. That is what lets it draft something specific rather than a generic hello. Be honest here: a no is worth more to me than a polite yes.

12 of 16

How do you feel about an app writing the message for you?

This is the part I am least sure about, so please be blunt.

13 of 16

What would stop you actually using it?

Pick as many as apply. This is the most useful question here.

14 of 16

If this existed today, would you want to use it?

The honest answer, not the kind one.

15 of 16

Anything else?

The part I have not thought to ask about is usually the important one.

16 of 16

Can I come back to you?

You have just thought about this harder than most people ever do, so your reaction is worth a lot to me. Pick as many as you like, or none.

Leave it blank and your answers still count. I just will not be able to reply.