Anastasia likes others speaking and acting humbly. She also likes compliments. Once at her residence, you are to comply with all her orders, although there is room for being naughty while doing so.
There might be several ways to have her agree to a date. The following conversation is one of them:
Player: Good morning!
Anastasia: Good morning. A proper greeting. This is off to a good start.
Player: How should I address you?
Anastasia: Very good first question. Miss Anastasia should suffice.
Player: Yes, Miss Anastasia.
Anastasia: That’s what I like to hear.
Player: Is there something special you require of me?
Anastasia: I expect you to have some basic knowledge of doing housekeeping chores. Wouldn’t be a point to the whole thing otherwise now would it?
Player: I am not really good at those to be honest.
Anastasia: That is going to be a problem. For you.
Player: Is there a Master of the house, Miss Anastasia?
Anastasia: Not at the moment.
Anastasia: You would only have to satisfy me.
Player: I am happy I can focus on you and only you
Anastasia: Ah, a flatterer!
We will see how well you live up to those words.
Player: Could I maybe get a picture of you?
Anastasia: Why would I send you one?
Player: I could send one first if you want to?
Anastasia: Not good enough.
Player: So can I meet you?
Anastasia: We shall give it a try. Come to my residence tomorrow evening.
Anastasia: Don’t be late.
If you haven’t acquired any housekeeping skills, you still have time before you go and meet her. Anastasia is unlike the other dates in terms of time. She explicitly told you not to be late. That means you are going to have to set out an hour earlier. The notification will inform you about this at 5PM.
At her place you can put on whichever uniform is presented to you. Definitely perform the chores you were tasked with and then serve dinner and serve her during dinner. You will get lucky.