Thanks for the feedback and I'm glad you're liking the game!
Hmm, I'll take a look at Lily's and Hermione's coffee date scripts - there are probably some minor errors (I've probably mistyped something) that cause the game to throw an error to the player.
As for Anna, there isn't much indeed. She'll have a personal storyline eventually, but I'm focusing on fleshing out the club and school gameplay first. Same goes for Olivia, she doesn't have a lot to her, but certainly more than Anna. Both will get coffee dates and more story content once I'm done with other parts I'm currently busy with.