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Critical Role's Liam O'Brien refuses to create headcannon for Caleb & Essek's romance: "I don't want to limit the future"

We know that Caleb Widogast and Essek Thelyss get together at the end of Campaign 2, which is where we get the story of The Mighty Nein. But what happens next? Liam O'Brien doesn't want to narrow down the possibilities

News by Grant DeArmitt, Staff Writer

Published on Tue Apr 21 2026

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If you're a Critical Role fan (and face it, reader, we know you are - why else would you be here?), you probably have some sort of headcanon regarding the one of the most popular couples from Campaign 2: Caleb Widogast and Essek Thelyss. Outside of Fjord Stone and Jester Lavorre, we'd be willing to wager that Caleb & Essek have earned the most time spent by fans imagining all the big and small moments of their relationship... although there is at least one Caeb/Essek shipper that purposefully tries not to do so.

That is: Caleb Widogast himself, Liam O'Brien.

O'Brien discussed this fact during a recent episode of Fireside Chat, Critical Role's regular fan Q&A on Beacon.tv. The subject came up when O'Brien was asked his opinion on who, between his Zemnian wizard and Matt Mercer's drow wizard, made the first move in the beginnings of their romantic relationship.

"Since that is largely post-Campaign 2," answered O'Brien, "And we can't stop building out the world, I don't want to arbitrarily decide right now. Because we could put them in a novel or we could put them in their own graphic novel or we could... who knows?"

Actually, someone might know. Just offscreen for this interview was one Dani Carr, Critical Role's Lore-Keeper-in-Chief, who said to O'Brien, "We have so many book plans."

Don't jump the gun here, Critters, this is absolutely not a confirmation that we're getting an update on the Caleb/Essek relationship in the form of non-actual play media. Although to be fair, we do know that a post-Mighty Nein Caleb will star in the upcoming novel Critical Role: The Mighty Nein--Children of Empire by Nibedita Sen. Point being - Liam knows that there's still plenty to explore in this much-shipped situation, and that he owes fans time and care in crafting that.

"I don't want to limit the future," O'Brien concluded. "[There are] infinite possibilities."

We appreciate that, Liam. That said, we hope that we do get to see one of them make a first move in an upcoming piece of media soon, if only so we can find out what a Kryn Dynasty pick-up line sounds like.

With two animated series on Prime Video, Campaign 4 in full swing, and so much more Exandrian lore to come, Critical Role is showing no signs of slowing down. That's why the adventuring party at Popverse are here to bring you everything we can from those nerdy-ass voice actors & Bo., including:

...and much, much more. Roll initiative, player. Magic awaits.

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Grant DeArmitt: Grant DeArmitt (he/him) likes horror, comics, and the unholy union of the two. In the past, and despite their better judgment, he has written for Nightmare on Film Street and Newsarama. He lives in Brooklyn with his partner, Kingsley, and corgi, Legs.