#CriticalRoleSpoilers
Caleb's crush on Jester was always a private thing, as Liam put it "selfish." A source from which he arrives to make her happy and expected nothing in return, even if part of him yearned for it. He will always ride or die for her as her friend.
#CriticalRoleSpoilers
If Fjord makes her happy, I think he'll support that relationship 100%. I think he sees Fjord as less likely to hurt her with his baggage. I'm sure he'll do what he can to help them succeed and be there to confront Fjord if he goes astray.
#CriticalRoleSpoilers
(I don't think he will. Fjord seems very conscious of also not wanting to hurt her with his baggage or make her feel like she has to stay if what they want diverges.)
#CriticalRoleSpoilers
Caleb is used to a life of being happy people he cares about have what makes them happy, even when he fellas those things are no longer for him. Perhaps because of that. He sees how fragile the simple his of life are, and wants to spare others his pain.
#CriticalRoleSpoilers
Even if part of him is a little jealous. He doesn't let that sour his care. The scene in 120 of him noticing the relationship had changed, was small but significant closure. He can take comfort in knowing where he stands now.
#CriticalRoleSpoilers
And maybe let himself more fully move on to Essek, who he feels is a mirror to his baggage, although maybe that's unhealthy trauma bonding. Or maybe their deep knowing will help them move forward together.
#CriticalRoleSpoilers
Or Caleb romantically keeps to himself, seeing too much danger and maybe too many parallels to Astrid. As I said, he's used to living with yearning he knows is more dangerous than he should really touch.
#CriticalRoleSpoilers
He cares deeply for Essek and is attracted to him, but he also mistrusts him. Maybe as he mistrusts himself. He's afraid what hubris and ambition they might enable in each other. And also, Essek's home is Xhorhas and Caleb's is the Empire.
#CriticalRoleSpoilers
One would always yearn for the other country, wherever they went together. Star crossed, in that way. And dangerous as Xhorhas is for Essek, the Empire is far more dangerous and discriminatory. Could Caleb always live in the dark as an ex-pat?
#CriticalRoleSpoilers
On the other hand, loneliness and isolation has driven them both to dark places where their ambition was twisted by evil people, so maybe the mortifying ordeal of being tritely known and loved is well worth it. They could check each other.
#CriticalRoleSpoilers
Anyway, much to think about. The web of relationships in this show is so very, very different, more complicated, and more real than most shows. It's fun to explore how they intertwine and drive people, even when romance isn't or is no longer the goal.
#CriticalRoleSpoilers
However they configure themselves will be with deep love and support that drives them to lift each other up and be somewhat protective.
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