To get this scene you have to finish both of the bareshade expansion and road events, see the 'Clash w/ Barrel' event at the bar (enter bar at night w/ bandit morale at least at 25), and finish asking about Logan's work. After that enter your home in Bareshade during the evening and he'll randomly show up. Sleeping w/ him is the bad option, so I recommend saving before if you just want to see the scene.