Nice, i have similar idea for a while, with some additional features:

- Easy to use, my idea is just have a telegram/facebook chatbot, people talk to it in plain English, what is their message, the receiver and the watch time.

- Multi reminder: For example, you can set 3 days to send message 1, 10 days to send message 2 and so on. The idea is the message 1 can be "You are receiving this message because XXX has something to talk, please contact them if you can ASAP". So that if you forgot to "kick the dog" 1 day, your deep personal message won't be sent immediately.