Four minutes, three questions
The most useful routine anyone has built with Dialogue app is also the smallest. What is on today. What are you dreading. What would make it a decent day even if the dreaded thing goes sideways. Answer honestly, get a reply, close the tab.
Why it works
Naming the thing you are avoiding removes most of its weight, and saying it to a character who will ask about it again tomorrow removes the rest. It is accountability without a spreadsheet.
Keeping it light
A check-in stops working the moment it becomes homework. Skip days. Send two words. The bright, practical personalities here are written to pick up a broken streak without a word of reproach.
Evening version
The same routine reversed works at night: what happened, what you handled better than expected, what you are putting down until tomorrow.