I drew the art for these scenes, but never managed to find time to actually write them. Possibly this update since I am expanding the dance girls.
Basically if you have slutty perks, high enough sex knowledge or pass an int check, when you see Dani going alone then Sammy will know whats going on. Then when you speak to her next time Sammy will bring it up in conversation (this is where most people fail because they cheat jump to the next event without having spoke to Dani). After the next event, Dani will ask you to wait for her while she goes with the guy.
The game is sort of designed to be played spread out. Speak to many characters and do many things. So usually events will trigger in a somewhat natural way. A fair few people though tend to focus down specific content or characters without having progressed much of the rest of the game and end up blocked from specific content. A good example is some of Robins stuff. People will focus on her but not done any bar work, spoke to soccer boys, beach or anything else. So conversations to find out more about her just doesn't come up. You can't find out Robin gets off on the idea of you being a pub whore if you don't work the pub.
As pointed out while I wrote this, it's kinda by design. Sandbox games where you are in complete control ends up getting weird giving full control. One moment you are a submissive sex slave, the next you are murdering criminals with chopsticks. To avoid that I gave Sammy her own will and character and keep everything in line and consistent with that. So it does mean you more play the role of the devil on Sammy's shoulder and not actual Sammy. Think of her more like a Tamagotchi. Keep her happy and she will do what you say. Upset her and she will tantrum.
