hii, so to start those routes u gotta reject being a proxy on chapter 1, so in chapter 2, Jeff will guide u through the mansion.
For Jeff, u have to give him his underwear when he tells u to go to his room (while u r in his room, click the accumulated clothes on the floor.) - that'll increase the bar a lot.
To meet Ben u must go to the basement and interact with the game on the floor.
Then, they'll tell u to choose a weapon of the closet and go outside, there u'll meet Eyeless Jack. (u have to enter his room outside the mansion.)
//I still couldn't figure out how to get the gallery thing for Eyeless Jack on this chapter, so if anyone knows, tell me please TT//
Ok so, after that u have to choose if you'll go with Jeff or Ben, that will get you to their routes and to get their images in the gallery.