genuinely forget the middle step... think it's something to do with a late night event in the living room where you watch the news? It's been a minute, so I'm probably wrong... but it should be the trigger to talk to Gypsy about it then it'll lead to a silly event that let's you meet the police lady at the station at night and train with her
ya, I haven't played in a minute while I wait for updates to stack up... but I think the simplified path is event at apartments > event at gym > news event in living room in afternoon or evening > talk to Gypsy and do event that introduces cop > meet cop at police station at night and train with her... since you just figured it out, is that accurate?