This used to exist, it was called OhLife. They would email you every day and say "What's happening in your life" and "Hey do you remember this?" with one random email from your history included. I always liked this service and was sad when they shut down. Pretty sure I started using it due to a post right here on HN.
I've been continuing to use DailyDiary since.
I have an apps script that automatically adds a draft response to these prompts, which still starts with an "Oh Life, ...." salutation. The script also adds the day's weather report to the bottom of the draft. My todo list has an item to add top and random tracks from my scrobbled music listening for the day.
In the evening I fill in the body of the response with reflections from the day and off it goes.