All you have to do is click the +Affection option in a character's room. You won't see irrelevant content, only relevant content. Such as Kali talking about her job while she works there, or that switching to talking about her school while she goes there.Will these be retroactive in some way? Or will they only be accessible in a new playthrough? I like the dates because it's nice to learn more about the characters but I don't think I'm willing to go through a whole new playthrough just for that.
These dates are meant to dynamically change with their friendship so they only talk about current events.