Are we really in the territory of shooting blanks until something actually sticks? Even for the sake of working on your people skills, you can't just keep trying to start conversations with the same person in such a short time span without making yourself look suspicious or overbearing.
They say this isn't like a dating sim, but they allow the dating sim mechanic that people don't think about one particular person continuously trying to latch onto them like it's nothing. I get the point the author's trying to make, but at least space it out between a number of different people so it doesn't look like he's trying to hamhandedly hit on her.