Relationship between Caleb and Essek

Relationship
Caleb Widogast and Essek Thelyss enter a romantic relationship at some point after the campaign and are life-long friends. Their initial friendship is very guarded, as Caleb and the rest of the Mighty Nein are hesitant to trust Essek. As Essek teaches Caleb dunamancy and helps the Mighty Nein travel around Exandria, Caleb and Essek recognize each other as kindred spirits, and Caleb is attracted to Essek. Their relationship is shaken when Essek's identity as the traitor is uncovered, but reconnect when Essek accompanies Caleb and the Mighty Nein into Aeor, discussing their mutual attempts at pursuing redemption and planning to return to Aeor together in the future. Their eventual adventures lead to an even deeper connection and a romantic relationship.

Liam O'Brien has stated that outside of the Mighty Nein, Essek’s "probably the only person that Caleb would see as a friend that he’s made. Which makes him a rarity in all the NPCs." Liam has also said that "Caleb's relationship to Essek was many things, is many things," confirming both care for Essek and attraction to Essek, but that at the moment of the forehead kiss, "it wasn't just 'I'm really attracted to you and I want to be with you'... there [was] a lot at stake", and that the speech and kiss were intended to keep Essek "on the rails". While everything he said to Essek was true, in that moment Caleb was drawing on past experience and past training to make sure things went the way they needed to go. He also said that Essek was not high on the list of things that Caleb needs to work on. He has said that "Essek is not like the Nein; Essek is brilliant and gets it in the way that Caleb gets it, and that was great [for Caleb] to be around," but that Essek is "fucking toxic" and dangerous. Caleb seems to worry that he and Essek are too much alike.

History
After their arrival in Rosohna and being declared Heroes of the Dynasty for their return of one of the missing beacons, the Mighty Nein came under Essek Thelyss’s supervision. After his den gifted the Nein with the Xhorhaus, Essek came by to see how they were settling in. Caleb inquired about the avenues of learning dunamancy and after he impressed Essek with his Cat’s Ire, Essek offered to give him a few lessons. This was the beginning of a meaningful intellectual relationship between the two wizards through which Caleb learned dunamantic spells and the Transmogrification spell was developed.

Caleb asked Essek to try to delay the execution of a captured scourger, and Essek managed to stay the execution for some time. He accompanied Caleb and the rest of the Nein when they went to interrogate her. After the scourger attacked Caleb, Essek quickly used his magic to suspend her in midair before dispatching her on Caleb’s signal.

Essek aided the Mighty Nein by teleporting them to many hard-to-reach locations. On one of these occasions there was a miscommunication about their precise destination. Caleb helped convince Essek to teleport them a second time by apologizing and placing a hand on Essek’s forearm. Essek's reaction seemed to be confusion and irritation.

The two wizards have acknowledged each other as kindred spirits. During dinner at the Xhorhaus, Essek said that Caleb understands his intellectual curiosity and that he sees “a similar spark” in him. After Essek’s confession to stealing the beacons, Caleb said “the difference between you and I is thinner than a razor” in reference to their past wrongs, after which he kissed Essek on the forehead.

While talking to the Mighty Nein at Vurmas Outpost, Essek struggled to hold eye contact with all of them, but could not make eye contact with Caleb at all. He at last looked at Caleb while hinting that he hoped reverse time and fix his mistakes. As Caleb left Essek's quarters, he caught Essek by the arm and told him to breathe, saying "Not weeks, not years. It takes time." Essek replied, "Indeed."

After returning to Vurmas Outpost, the Mighty Nein decided to ally with Essek in their return to Aeor. Essek journeyed into Aeor with the Mighty Nein and fought alongside them. The night before the Mighty Nein ambush the Tombtakers, Caleb takes Essek up to the chamber of possibility on the ninth floor of Widogast's Nascent Nein-Sided Tower. Essek asks him what his ultimate goal is. Caleb replies that he is no longer sure, but what's happening now is more important. He still means to atone, but now believes there may be more than one path to that atonement. They discuss their past sins, though Essek insists that his are worse than Caleb's. Caleb hopes that if he does enough, he will be able to carry his sins more easily.