Relationship between Caleb and Yasha

Relationship
Caleb and Yasha's backgrounds are eerily similar. Both experienced tragedies that resulted in the deaths of those they loved, and both blamed themselves for those deaths. Both were on the run from their pasts when the campaign began, and harbored feelings of guilt and self-loathing. Both tended to be introverted and socially awkward. Yasha, however, had the direct intervention of the Stormlord in her life, and his gift of visions and dreams of her past allowed her to receive the forgiveness and blessing of her former wife, Zuala, urging her to break the chains of the past and move on to a healthy relationship with Beauregard.

History
Initially, Caleb liked Yasha due to their similar personalities and mutual dislike of, and uncomfortableness with, close contact. When Caleb asked her for advice regarding social situations, Yasha listed off a few things that she believed would make people like Caleb more: talk to people if they talk to you, be nice, eat with your mouth closed, wash your hands and hair. He wrote this all down. She shaved his face with her sword after Caleb mentioned that he missed being clean-shaven. Caleb asked if this made them friends, and Yasha said that it did. Later, he specifically asked that she be the one to buy his new clothes for him in Rosohna.

Yasha learned that Caleb had also killed his family from Nott, who slipped and shared that information with her while they were both on watch inside the tunnels leading to the King's Cage. When Yasha was taken by Obann, Caleb was one of the most insistent of the party that they save her.

After Obann was defeated and Yasha was set free from his influence, they grew closer. One night on the road, Yasha asked Caleb for guidance on how to move forward despite her guilt. He told her that his guilt was old and he was accustomed to it; that it was easier with people around "to make you feel more like you." Yasha admitted that although anger was an emotion that she knew how to deal with, forgiveness was harder, and Caleb responded that even if they could never entirely wash their hands of guilt, they could use it to leave something better in the world. When Yasha suddenly asked, "Do you love her?" Caleb seemed to panic. Yasha told him that, as someone who had lost someone they loved very much she knew how important it was to say things before it is too late, but he replied, "It's too late, Yasha. It's too late," and turned away. When Yasha seemed to be developing a romantic relationship with Beau while on Rumblecusp, Caleb offered his support. He told her she deserved her newfound happiness and encouraged her to allow herself some happiness. Yasha then gave him a big hug. Caleb also provided Beau and Yasha the use of his tower for their date, making the multiple temporary modifications that Beau had requested of him.

Quotes
Caleb: Who? Yasha: I don't need to tell you who. I'm sorry, I-- as someone who has lost someone that they love very much, I know how important it is to say things before it is too late. Caleb: It's too late, Yasha. It's too late.
 * Caleb: I see hesitation and regret in you. And it is like a mirror. I know regret, and I regret, I regret, and unless my intuition is very off, you know regret.
 * Yasha: Do you love her?
 * Caleb: Listen, I can't give myself this advice, I don't think I can convince myself, but I can maybe try to convince you. You've been doing good for this group, you've been doing good for you. You have worth and value, and a promise of something. [...] We're the quiet ones, so I feel like it would do us some good to talk more, get out of our own skins a bit. [...] Yasha, let yourself a little happiness. Even if it's helping other people.