OKAY TESTED IT OUT! It is definitely has to be a glitch caused by the advance day cheat, I advanced the day straight to the afternoon as soon as I woke up, asked Mom to go out, and was appear to text someone to babysit. Looks like an overuse of that cheat causes the game to forget what day it is on, so it thinks you are on a day where you already asked to get a babysitter. I think this explains why I got the glitch on a new save cause I kept advancing the day to get all of Dizzy's stuff in order to unlock the babysitting option. So I'm guessing you guys that aren't getting the glitch are not spamming that cheat then right? Cause you if you are then I'm still lost lol