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 also "fucking toxic" and dangerous as he and Caleb may be too much alike.

During their first journey into Aeor with the Mighty Nein, Caleb and Essek discuss their past sins and how they might be able to carry them more easily. Though Caleb jokes that two wizards together are "fucking trouble", they also hold each other accountable, with Essek ensuring that Caleb stays focused on the task ahead of them in the records room. While they are both compelled by the possibility of going back and changing the past when they find the T-Dock chamber, they eventually return together and Essek declares he "wouldn't change a thing" as his past mistakes have brought him to the room with Caleb now, and Caleb turns the chamber to dust.

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.

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. Afterward, Essek and Caleb shared another dunamancy lesson. Essek admitted that sharing this magic could put him at risk, but said this was an extension of his trust in Caleb and the Mighty Nein. Caleb said that they were friends now, and Essek replied, “I like that.”

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 soon began to acknowledge each other as kindred spirits. During dinner at the Xhorhaus, Essek said that Caleb understood his intellectual curiosity and that he saw “a similar spark” in him. Caleb and Beau walked Essek home after dinner, and Caleb told Essek that he thought they shared interests. He sympathised with Essek's feeling of having expectations placed upon him. Essek said that he saw a great deal of pain in Caleb's eyes, and believed Caleb was "capable of more than you give yourself credit for." Caleb remarked to Beau that there were many "fascinating" things about Essek.The next morning, Essek invited the Mighty Nein to breakfast and offered to work with Caleb and Nott on the Transmogrification spell they were developing. When the three completed the spell, Caleb told Essek that he was “amazing” and pulled him into a hug along with Nott. As the Nein departed, Essek touched Caleb’s shoulder and asked if he could make his own copy of the spell. Caleb willingly agreed.

When the Mighty Nein encountered Essek in disguise as Dezran Thain, Caleb watched through Frumpkin as Dezran met with Ludinus Da’leth and was revealed to be Essek. Caleb felt like a fool, since he had just allowed himself to start trusting Essek. However, he noticed that Essek seemed conflicted and thought the Nein might be able to talk sense into him.

When the Mighty Nein questioned Essek aboard their ship, Essek confessed to having given two Luxon beacons to the Cerberus Assembly out of a desire to uncover their secrets. Caleb knelt and turned Essek's face to his, saying that he understood such ambitions. He pleaded with Essek to find his better self, saying, “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.

When the Mighty Nein learned that Essek was in Eiselcross, Caleb was uncertain that he could be trusted to help them. He feared that Essek might be tempted by the knowledge offered by Cognouza. When the party eventually reunited with Essek 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 to 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 appeared deeply moved when Caleb said that they trusted him over Trent Ikithon. Essek journeyed into Aeor with the Mighty Nein and fought alongside them. The night before the Mighty Nein ambushed the Tombtakers, Caleb took Essek up to the chamber of possibility on the ninth floor of Widogast's Nascent Nein-Sided Tower. Essek asked him what his ultimate goal was. Caleb replied that he was no longer sure, but what was happening now was more important. He still meant to atone, but now believed there might be more than one path to that atonement. They discussed their past sins, though Essek insisted that his were worse than Caleb's. Caleb hoped that if he did enough, he would be able to carry his sins more easily, and Essek said he understood.

The two wizards continued to rebuild their bond as they travelled through Aeor. In the Genesis Ward, Essek kept watch over Caleb as he gathered items from the record room. Concerned about the eyes appearing on Caleb’s body and Caleb’s apparent distraction, he urged Caleb to remain focused on their goal and admitted to worrying about him. As the party descended to floor B-9, Caleb began to “showboat” around Essek using a Fly spell. Essek responded by casting Fly as well and doing the same. Caleb and Essek worked together to examine the Rejuvenation device and the Temporal Dock, and Essek expressed hopes that they could return to Aeor together someday for further study. Jester remarked to Caleb that she thought Essek was “coming onto you”, to which Caleb telepathically responded “it’s complicated.”

Essek repeatedly looked out for Caleb during combat, asking after his wellbeing when the party was attacked by Aeorian hunters. In the fight with Lucien, Essek used his combat turn to pull Caleb free from the rubble of the collapsed tower. Later, during the fight with Trent Ikithon, Essek sacrificed half of his movement speed to drag a prone Caleb out of melee with Eadwulf. Caleb likewise showed concern for Essek during their travels together; in his giant ape form, he waved a wounded Essek at the clerics in attempt to make them heal him, and later freed Essek from being charmed by Gaudius during the battle with Lucien.

When Essek eventually returned to Vurmas Outpost after Trent Ikithon's defeat, Caleb kissed his cheek and pulled him into a deeply empathetic hug, telling him not to be a stranger and to be kind to himself. Around six months to a year after Trent Ikithon's defeat, Essek happily agreed to revisit Aeor with Caleb, and they spent some time fighting through the ruins together to reach the Temporal Dock. Essek decided that he didn’t wish to change a thing about his past, as his mistakes had led him to this moment with Caleb. He offered to assist Caleb if he wished to use the T-Dock, but Caleb destroyed the dock instead, to Essek’s approval. After some time and further recovery, the two began a romantic relationship; eventually, they split up, due to the difference in human and elven aging, but remained close friends.