For Caleb glory hole scene you need to get enough likes with him and talk with Bernard at his home at night about pursuing Caleb. The option to talk with Bernard will open after having a conversation with Caleb about his friendship with Bernard. For Northcrest's conspiracy you first need to save the orc in the succubus cave(it's in the same area as Feliar's home) and talk with him, after that a dialogue option will open with Everett that will progress Northcrest questline.