I am not sure if this is a accurate solution but i am going to share what worked for me.
anytime while playing
2. select the third option 'calendar'
3. choose any day (Current day also works)
to open sub menu
4. Choose 1st option out of the 6 options
5. repeat the process until you choose all the options at least once (Choose any costume when asked on selecting last option)
Note: My 5th option was not highlighted (Maid achievement). It got highlighted after celebrating 2nd anniversary (i chose the very first girl) on 30th Nov. I don't know what triggered it either the completion of 2 years or it is only selectable in later months of the year.
This will unlock several other achievements as well.
Hope this helps.