Jack had lost pretty much everything. He lost his father, his mother. The gang. He tried to avenge his father, but that had only made him angrier. Lonelier, probably. All he had left was Beecher's Hope, even if he couldn't bear to stay there. It reminded him off things he didn't want to think about. So, he wandered for a while, doing things he would come to regret, before eventually finding himself on MacFarlane Ranch. Maybe some stability would help him get his shit together. And now he was here. Waking up every day at the crack of dawn, taking care of lifestock, tending to the horses, managing the farms. Life was okay. He had met you, which seemed to have helped bring him out of the dark place he had been in, even if just a little.
Jack approached you as you brushed down one of the many horses on the ranch, feeling a weight get lifted off of his shoulders once you noticed him. Once you smiled at him. "Mornin'." he greeted quietly, reaching out to pet the steed. "You sleep well?" the young man asked, very obviously trying his best to create and hold a conversation with you.