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Critical Role Wiki
Critical Role Wiki


Shadowgast Saturday Sky

Fan art of Caleb and Essek, a decade or two down the line, by saturdaysky.[art 1]

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.

Thinner Than a Razor

Fan art of Essek and Caleb, by GalacticJonah.[art 2]

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."[1] 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,"[2] but that Essek is also "fucking toxic" and dangerous as he and Caleb may be too much alike.[3]

Shadowgast surpriseimbored

Fan art of Caleb and Essek, by Mikael.[art 3]

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", [4] they also hold each other accountable, with Essek ensuring that Caleb stays focused on the task ahead of them in the records room [5]. 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.[6]


Caleb and Essek noxarcanaart

Fan art of Caleb and Essek, by heidzdraws.[art 4]

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.[7] 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.[8] This was the beginning of a meaningful intellectual relationship between the two wizards through which Caleb learned dunamantic spells.[9][10]

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.[11] 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.”[12]

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.[13]

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.[14] 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."[15] Caleb remarked to Beau that there were many "fascinating" things about Essek.[16]

Both Damned - Omegasama

Fan art of Caleb and Essek, by Omegasama art.[art 5]

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.[17][18] As the Nein departed, Essek touched Caleb’s shoulder and asked if he could make his own copy of the spell. Caleb willingly agreed.[19]

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.[20] 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.[21]

You listen to me. I know what you are talking about. I know. And the difference between you and I is thinner than a razor. I know what it means to have other people complicate your desires and wishes. And I was like you. Was. I know what a fool I have been for years, and I'm looking at him as if I am looking in a mirror.
Caleb's speech to Essek after his confession [22]

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.[23]

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.[24] 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.[25] He at last looked at Caleb while hinting that he hoped to reverse time and fix his mistakes.[26] 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."[27]

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.[28] 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. [29]

Shadowgast OffbeatWorlds

Fan art of Essek and Caleb sharing a moment mid-battle, by Stephanie Brown.[art 6]

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.[30] 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.[31]

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.[32] Jester remarked to Caleb that she thought Essek was “coming onto you”, to which Caleb telepathically responded “it’s complicated.”[33]

Shadowgast eyezpike

Fan art of Essek and Caleb, by eyezpike.[art 7]

Essek repeatedly looked out for Caleb during combat, asking after his wellbeing when the party was attacked by Aeorian hunters.[34] In the fight with Lucien, Essek used his combat turn to pull Caleb free from the rubble of the collapsed tower.[35] Later, during the fight with Trent Ikithon, Essek sacrificed half of his movement speed to drag a prone Caleb out of melee with Eadwulf.[36] 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.[37][38]

Shadow & Fire - Lap Pun Cheung

Fan art of Essek and Caleb, by Lap Pun Cheung.[art 8]

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.[39] 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.[40] 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.[41] 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.[42][43][44]


Around six months after the events of Campaign 2, and within two weeks after the battle with Uk'otoa, Caleb waited at his new home in Rexxentrum for Essek to visit. When Essek arrived, they caught up briefly on recent adventures while standing in the doorway. Caleb invited Essek inside, saying "Come, Dear." and Essek kissed Caleb as they entered the home together. [45]

Following the events of "The Mighty Nein Reunited Part 2 – Uk'otoa Unleashed", Essek stayed with Caleb in Rexxentrum, enjoying a quieter life while laying low and helping Caleb with his teaching job at the Soltryce Academy. Essek also started working on his own research projects and assisted the Cobalt Soul. [46]

In 843 PD, Trent Ikithon addressed Caleb via Magic Mouth in the library of the Cobalt Soul in Zadash, threatening to reveal Essek's treachery to the Bright Queen, which angered and worried Caleb. Caleb called Trent 'an absolute brick of shit' after hearing this. Later, Jester expressed worry that Trent might hurt Essek and Caleb agreed, saying, "Yeah, I don't think we have much time. A day or two. I'm nervous to wait longer." [47]

Campaign Three

While talking with Astrid Becke and Bells Hells in 843 PD Essek referred to Caleb as his 'partner' over multiple instances. Fearne Calloway asked Essek if he had someone back home and Essek said that he did and also said that "He is kind, and he is smart, and he is so strong... of heart." Essek also excused himself to send to Caleb before bed, with the implication of it being a habit. [48]

Essek used Leomund's Tiny Hut, preferring to keep the dome's amber coloring often used by Caleb. He also briefly discussed the effects of wild magic in Aeor by recalling a time he was turned into a salmon and Caleb had to carry him for 'a while'. According to Essek, he and Caleb returned to Aeor together three times after their initial visit in pursuit of the Tombtakers. [49]

It's also suggested that Essek was learning Zemnian, Caleb's first language, when he told Imogen Temult 'Gesundheit' after she sneezed and added that his partner taught him this word. He additionally picked up some Zemnian swear words. [50]


  • During the break of "A Tangled Web" (2x77), which took place immediately after Essek killed the scourger and Caleb persuaded him to give another dunamancy lesson, Liam tweeted: "What's sexier than wizards NOTHING".[51] This phrase has since become popular within fandom.
  • Matt speculated about Caleb and Essek living together, organizing and labeling household items. [52]
  • Matt stated that Essek took up knitting as a hobby. Cast members and fans have speculated that the purple scarf Caleb wore in "Red Moon Rising" (3x50) was knit by Essek. [53]
  • Matt referred to their relationship as a 'courtship'. [54]


  1. See "Talks Machina #143: 'Family Shatters'" (TMx143) at 0:55:17.
  2. See "Talks Machina #147: Discussing Up to 'New Homes and Old Friends'" (TMx147) from 1:27:47 through 1:29:40.
  3. See "Talks Machina #153: Discussing Up to C2E123 - Fair-weather Faith" (TMx153) at 1:06:23.
  4. See "Hunter and Hunted" (2x133) from 3:26:25 through 3:33:00.
  5. See "The Genesis Ward" (2x135) from 1:24:20 through 1:28:20.
  6. See "Fond Farewells" (2x141) at 6:39:05.
  7. See "In Love and War" (2x57) at 0:46:33.
  8. See "Domestic Respite" (2x62) at 1:49:15.
  9. See "Domestic Respite" (2x62) at 1:52:37.
  10. See "A Tangled Web" (2x77) at 1:34:17.
  11. See "A Tangled Web" (2x77) at 1:15:56.
  12. See "A Tangled Web" (2x77) from 2:01:42 through 2:02:00.
  13. See "Through the Trees" (2x79) at 0:29:28.
  14. See "Stone to Clay" (2x91) at 0:38:43.
  15. See "Stone to Clay" (2x91) from 1:37:10 through 1:47:45.
  16. See "Stone to Clay" (2x91) at 1:39:08.
  17. See "Stone to Clay" (2x91) from 3:24:23 through 3:24:42.
  18. See "Stone to Clay" (2x91) at 3:26:42.
  19. See "Home is Where the Heart Is" (2x92) at 0:30:14.
  20. See "The Fancy and the Fooled" (2x97) at 1:03:36.
  21. See "The Fancy and the Fooled" (2x97) from 1:14:19 through 1:14:55.
  22. See "The Fancy and the Fooled" (2x97) at 3:05:29.
  23. See "The Fancy and the Fooled" (2x97) at 3:56:14.
  24. See "Nothing Ventured, Nothing Gained" (2x122) at 3:00:02.
  25. See "A Walk to Warmer Welcomes" (2x124) at 2:54:54.
  26. See "A Walk to Warmer Welcomes" (2x124) at 3:20:36.
  27. See "A Walk to Warmer Welcomes" (2x124) from 3:28:03 through 3:28:39.
  28. See "Into the Eye" (2x131) at 4:09:35.
  29. See "Hunter and Hunted" (2x133) from 3:26:25 through 3:33:00.
  30. See "The Genesis Ward" (2x135) from 1:24:16 through 1:28:23.
  31. See "The Genesis Ward" (2x135) at 3:40:18.
  32. See "The Genesis Ward" (2x135) at 2:52:07.
  33. See "Hell or High Water" (2x136) at 58:25.
  34. See "The Streets of the Forgotten" (2x134) at 3:40:42.
  35. See "Long May He Reign" (2x140) at 2:19:00.
  36. See "Fond Farewells" (2x141) at 2:33:24.
  37. See "Hunter and Hunted" (2x133) at 59:14.  Capeleb encourages the clerics to heal Essek.
  38. See "Rebirth" (2x139) at 3:25:19.  Caleb dispels the charm effect on Essek.
  39. See "Fond Farewells" (2x141) at 4:49:02.
  40. See "Fond Farewells" (2x141) at 6:38:14.
  41. See "Fond Farewells" (2x141) from 6:40:00 through 6:46:18.
  42. Phrased as "would be together for a while."  See "Fond Farewells" (2x141) at 6:46:23.
  43. Liam confirmed that they were in a romantic relationship on twitter
  44. Matt confirmed that they were in a romantic relationship on twitter
  45. The Mighty Nein Reunited Part 2 - Uk'otoa Unleashed
  46. Swordgate
  47. The Mighty Nein Reunion: Echoes of the Solstice
  48. Gathering of Needs
  49. Shadows New and Old
  50. Shadows New and Old
  51. Twitter logo (@VoiceOfOBrien) on Twitter: "What's sexier than wizards NOTHING" (2019-09-05). See also CritRoleStats' "Livetweets of 2-77 A Tangled Web" for the timing of the tweet.
  52. From Dusk Till Faun


  1. Fan art of Caleb and Essek, a decade or two down the line, by saturdaysky (source). Used with permission.
  2. Fan art of Essek and Caleb, by GalacticJonah (source). Used with permission.
  3. Fan art of Caleb and Essek, by Mikael (source). Used with permission.
  4. Fan art of Caleb and Essek, by heidzdraws (source). Used with permission.
  5. Fan art of Caleb and Essek, by Omegasama art (source). Used with permission.
  6. Fan art of Essek and Caleb sharing a moment mid-battle, by Stephanie Brown (source). Used with permission.
  7. Fan art of Essek and Caleb, by eyezpike (source). Used with permission.
  8. Fan art of Essek and Caleb, by Lap Pun Cheung (source). Used with permission.