Make her comfortable next to you by teasing and jokes...
And for you I suggest you to use phrasal transition:
Ohh that reminds me of...
This is like when...
Yeh, thats great because...
You think about it like that because...
or
Just change the subject to something more casual since your openers are usually about the school... Just w8 for the right 'word' which is easy to connect with something that is not about the school.
Example:
You talk about something about school and you say... Ohh i wish we have our schools organized like in Europe. I would like to go to school there... Anyway since im talking about the Europe, have you ever been there?... (traveling, europe, where she would like to go, why would she like to go, why not... etc). Thats just example, think of something like that

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