Essek probably realized he was in love or at least had feelings for Caleb during that fight in Cognouza. Because he truly went feral every time Caleb got hurt or went down.
Caleb getting crushed by a building? Essek uses fortune’s favor to pull him out.
Caleb goes down and then comes back up? Essek uses an 8TH LEVEL gravity fissure on Lucien.
Caleb gets impaled and killed? Essek is screaming and holding him.
Like after this battle, in the Blooming Grove, Essek probably had the realization that “oh no, I love this man.” Because the Nein all had moments of going down. Jester, Veth, Cad almost dropped. And Essek definitely cared and was worried! But Caleb? Caleb enacts such raw and visceral emotions from Essek, who even after becoming friends with the Nein is still reserved on some level.
And of course Essek wouldn’t tell him yet at the Grove because how could he? Caleb’s past just came back to try to kill him and he knows that as much as he wants to, and Caleb even asks him to come with them, Essek had to do some soul searching of his own first. But pining Essek during their stay at the grove. But a different sort of pining. Because it is clear that Caleb would reciprocate on some level. Caleb’s affections are very clearly abundant at that time. But this pining of not yet, not our time. Knowing that you want to be a better person before sharing your life with someone.
And then Aeor. Essek willing to help Caleb time travel if it will make him happy. If it was what Caleb wanted. He’s fully in love by Aeor round two.
In Cognouza, Essek realizes he’s in love with Caleb and by Aeor he knows he wants to spend the rest of their lives together.
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