In the tuning file for "Ask about day", "Check in on" is just an alternative visual variant that should only display if your sim has the Supportive family dynamic.
Supportive caregivers will have the text changed from 'Ask about Day' to 'Check in on' when interacting with the family member they support.
I only played without the new expansion pack for those two days between the update and pack release. I do remember seeing "check in on" during that time, but not since I got the pack since I don't have any sims with the supportive dynamic yet.
If it's showing up for people without the pack, then maybe the game is getting confused because family dynamics don't exist without the pack?
