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     Confirmed 
The last barrel on The List is for Percy's sister
Another theory proposed by Liam O'Brien - this time, speculating that the last barrel on The List is for any remaining de Rolo family members who may have been turned traitor by the Briarwoods. Most likely, this would be Percy's sister, who was the last person Percy saw alive.
  • Jossed in Episode 30. See above.
  • And then un-Jossed and confirmed in Episode 34 - Cassandra's name is added to The List after she betrays Vox Machina to the Briarwoods.

Cassandra de Rolo is still alive
In the Feast, Percy mentions that his younger sister Cassandra freed him, and that she was the last of his siblings he saw alive. In the same episode, the Briarwoods casually mention that something in the forest around Whitestone is making it difficult for them to export timber, and Vox Machina offers up their services to help deal with it. It's possible that it's Cassandra, or another living de Rolo, hassling the Briarwoods in any way they can.
  • Confirmed in Episode 30 - Cassandra is living in the castle, feeding information to the rebellion. However, she was also in league with the Briarwoods until they were defeated, after which she became one of the good guys again.

The Briarwoods are vampires/demons/etc
It's pretty clear that they're not human, what with them calling Vax "delicious" and all. The most obvious consensus is that they're vampires, but succubi and glabrezu have also been suggested.

The Slayer's Take Characters will come back, probably as Big Damn Heroes
People adored Zahra, Lyra, Kashaw and Thorbir, and it would be a shame not to see them again. More importantly, they left behind a few interesting plot threads, such as Zahra's creepy father, Kashaw's creepy god, and, of course, The Big Damn Kiss. Also (except for Kashaw, whose whereabouts are unknown) they're a band of monster hunters, so they're ideally suited to show up just in the nick of time when Vox Machina is fighting something nasty. And Kashaw is a cleric - now that they no longer have Pike around, he might be the ideal person to call should they ever need a resurrection performed.
  • Confirmed in episode 43.
    • Well, Kashaw and Zahra do at least, after a Noodle Incident brought the two of them together, while Thorbir had an NPC cameo (losing at games of chance). Lyra has as of yet not made another appearance.

Kynan will come back as a villain or rival
As Travis put it, "Dude, don't be mean to the kid — you've seen The Incredibles, right?"
  • Partially confirmed. Kynan came back under Dr. Ripley's sway when Vox Machina encountered him again, but seemed to change sides when Vax persuaded him.

The Chroma Conclave with collapse upon itself, with indirect help from our heroes.
Let's face it, Chomatic Dragons are very selfish and territorial, and it's clear the Red Dragon, Thordek is their boss due to dominance, and almost seem to subjugate the other three dragons. It could be reasonable that the smaller (yet still ancient) dragons could be persuaded to try to take dominion of the Conclave for themselves.
  • Partially confirmed. Raishan, the Green Dragon, is set on killing Thordak in order to discover the cure for her corruption. She does need Vox Machina's help to overthrow him, though.

After the Chroma Conclave is defeated, the next arc will focus on the ramifications of the "spinning orb of death"
A pretty obvious guess, here. The magic-draining orb has ties to Vecna, an arch-lich who aspires to be a god, and it hasn't been moved, stopped, or even explained since it was created. It's the only major lingering plot thread the characters have left to solve (besides the personal side quest of Keyleth's Ara'mente), especially now that they have gathered all the vestiges but one.

     Jossed 
The last barrel on The List is for Percy
Both the fans and Liam O'Brien have speculated that the unmarked barrel on Percy's pepperbox is for himself. Once he gets his revenge, he might be planning to rejoin his family.
  • Jossed as of Episode 29...Maybe. Scanlan explicitly asks Percy if the barrel is for him, Percy says no, and Matt doesn't call for any Deception checks. Then again, even asking for a Deception check would spoil the answer for the players, and the next words out of Percy's mouth are "even if it was, would I tell you?"
  • Fully Jossed in Episode 30. Percy explains that the unmarked barrel represents all the casualties that will occur as a result of him inventing his guns.
  • Jossed yet further in a different way: Percy/Taliesin was guessing. Cassandra's name appears on the last barrel when she betrays Vox Machina, though it's unclear whether she'd always been a target but only revealed at that moment, or the barrel was "to whom it may concern" until her betrayal marked it.
  • An even simpler explanation, he just might not have had any other names to add. The significance to the number of rounds a revolver can have is just ergonomics. Depending on the size of the rounds used, the cylinder has to get progressively wider and taller to accommodate.
  • Jossed with prejudice in the After Campaign Q&A. Matt reveals that Orthax would've kept Moving the Goalposts, and add six more names to The List, and then six more after that, and it would continue indefinitely. The last barrel was never meant for anyone in particular, and Orthax could have put any person's name on there to try and further his goals of corrupting Percy and absorbing souls.

Keyleth's vision was not of her death, but of the final part of the Aramente trials.
It's not likely that Matt would just kill someone from Vox Machina as a part of the plot, but it is likely that he'll find a way to make Keyleth's vision come true. There are plenty of spells of varying power that could forcibly turn someone into a tree, like Tree Shape, Polymorph, or True Polymorph. Note that True Polymorph is not a druid spell, but it would be easy to make an exception in Matt's world when they've built entire classes from scratch. The last part of the Aramente involves proving Keyleth's worth, as it would with any other trial, but this one is specifically for the worth of the bonds she has made on her travels. She may be forced into a tree shape, with the rest of Vox Machina called to her defense. That would also explain why the members of Vox Machina were shouting "for our Princess" in her vision.
  • In addition, this could be why Keyleth's mother failed her Aramente; there was nobody there to release her from her tree state. True Polymorph is permanent if concentration is maintained for one hour, so Keyleth's mother might still be out there somewhere as a tree.
  • Alternatively, the vision could be referring to a particular significant tree. In particular, it could somehow relate to the "cancerous tree" that supposedly conceals one of the Vestiges of Divergence in the Feywild.
    • Jossed in terms of the cancerous tree. The party confronts a different trial within in the form of Fenthras' wielder, Saundor.

Vax is a Death Seeker
It's pretty clear he's Not Afraid to Die, but his risks have become increasingly reckless as time goes on. Episodes 23 & 24, if you squint, read like Vax's bucket list. He gets a tattoo, plays pranks on Vex and Grog, tries to talk Kainen out of following him, tries to repair that relationship when it goes south by leaving Kainen a gift, confesses everything about K'varn and the Horn of Orcus to Gilmore (and even greets him with what could be both a First Kiss and a Last Kiss - on the cheek, mind.) He pays off the servants at the keep and repays his other debts. He apologizes to Gilmore for not being able to uphold their deal of spreading the word about Gilmore's glorious goods. He's getting his affairs in order. He even develops a sudden interest in religion and receives a symbol of Sarenrae from Father Tristian, i.e. preparing for the afterlife. And of course, to top it all off, he makes a series of incredibly stupid mistakes that get him trapped with the Briarwoods, which could easily lead to his death. Aside from depression or trauma - the latter of which could be very possible, considering how shaken up he was by the time in the Underdark - the only major thing we're missing is a clear reason as to why Vax would want to die.
  • Jossed during a Q&A. Liam O'Brien confirmed that Vax does not have a death wish.

Gilmore is Affably Evil
Sure, he's charming and charismatic and friendly, but it's pretty clear that his first priority is his business, and we don't know how far he'd be willing to go for it. Even when the Ho Yay with Vax gets intense, he always circles it back around to the business. It's also true that he has a lot of insider knowledge on Vox Machina, particularly now that Vax has told him about the Horn of Orcus. He'd have a great grasp of their strengths and weaknesses based on their purchases.
  • More specifically, some people suspect he's working with the Briarwoods, as both of them seem to have an interest in trade.
  • seemingly Jossed in episode 41 where it is revealed that he faced down and was nearly mortally wounded by an Ancient Red Dragon to save Sovereign Uriel's family, as well as Seeker Asum and Tofor Bratoris.
  • possibly confirmed in Episode 56, although the exact details are still unknown.
  • Jossed again: Gilmore was only replaced by Hotis the Rakshasa very briefly. He's still glorious and has been all along.

Kynan will not come back, because he's dead
Vax's suggestion that Kynan train himself resulted in Kynan seeking out something he couldn't handle and meeting an untimely end. This is supported by the fact that Vax couldn't find Kynan in the city in Episode 24. It's also compatible with the theory above - Kynan may come back as a spectre or other malevolent undead.
  • Jossed. Kynan is alive and well.

Kynan is now working for the Briarwoods
It's possible that the boy who was at the feast that Vox Machina thought that maybe they kind of recognized, is indeed Kynan and is already under the thrall of the Brairwoods, possibly even before the Briarwoods ever came to Emon.
  • Jossed: The boy in question is named Desmond. Percy likely recognized him because his father was a messenger for the de Rolo family.

Kynan will come back as a hero
He's probably even more ideally situated for a Big Damn Heroes moment than the Slayer's Take members. If Vox Machina gets into a particularly hairy situation in Emon, (which they are, as of Episode 24), he's in a perfect position to rescue them out of the blue.

Tiberius Stormwind will return to Vox Machina after he's been accepted by his family as a true Stormwind.
Once Tiberius has gained the full acceptance of his father, and the backing of the Draconian Council, Tiberius will rejoin Vox Machina, if only temporarily. He will find that his quest to find his missing artifacts less important than fitting in with both of his families (Stormwinds and Vox Machina).
  • Brutally jossed as of Episode 64: Tiberius Stormwind never got the chance to do either as he was revealed to have been killed in the attack on Draconia by Vorugal the Frigid Doom.

Gilmore is a dragon.
Yes, a literal dragon - specifically a silver dragon, since they're known to have shapeshifting abilities, and enjoy the company of humanoids. Matt has already hinted that there's more to him than meets the eye, and now with the arrival of the Chroma Conclave, Critters understandably have dragons on the brain.
  • Seemingly Jossed. Gilmore himself, when asked by Scanlan if he was a dragon simply said, "If you could make me one... that would be sexy." However, this could simply just be a ploy to throw off anyone from their suspicions.
  • Almost certainly Jossed. If he was anything more than he appeared, then the battle against Thordak would have been the moment to show it. Instead, he almost got killed a couple of times, and still was a very crucial part of that battle, but didn't show any more power than casting a 7th level spell.]

The one that Pike loves is... Grog.
Ashley Johnson has said that Pike left the Broken Howl for the one she loves, that it is someone from her backstory, and it isn't Scanlan. While her playlist seemed to indicate that the pair were Like Brother and Sister, she does go out of her way to try to impress the Goliath, such as when she cut the throat of the duergar with her mace, or (after he'd shown appreciation for Lady Kima's badassery) when she ran back to fetch torture implements for him. She risked her relationship with Sarenrae to try to get his approval...
  • This one seems likely. Though this may end up being a case of unrequited love, unless Pike spells it out for Grog. Because as well-meaning as Grog may be towards Pike, which is true considering that Grog and Pike would always have each other's backs no matter what anyway, most men don't really answer to subtle hints from women, much less a Goliath with an intelligence of 6.
  • Jossed, actually. The post-campaign Q+A revealed that Pike fancied Percy for a time (as some fans guessed from her giving him the Amulet of Life Saving).

Vex'ahlia will face an existential crisis stemming from the events near the end of Episode 44 due to her greed.
Because of the events at the end of Episode 44, it is likely that Vex'ahlia will temper her greed, and go through a crisis. This in turn will help her Character Development.
  • Given that in the very next episode, she steals a magic broom (from a guest party member, no less), her greed is getting less tempered if anything. Her alignment even shifted to Chaotic Neutral because of it, so her character may be developing in the opposite direction.
    • This could still lead to a temperance of her greed, after working out the crisis portion of her ordeal. Though it is likely, her death has made her even more jaded, and less heroic.
  • Partially jossed. She's facing a different existential crisis from her encounters with her father as well as Saundor. She's questioning her self-worth and wondering if the choices she made over the course of her life were the right ones.

Kynan Leore still has a part to play in the Chroma Conclave Incident
Out of all the allies that could have possibly helped in Emon, everyone is accounted for, except Kynan, who probably left the city long before Thordak and Co. arrived.
  • Jossed. Kynan reappears in the employ of Anna Ripley, and is thereafter taken to Whitestone to help protect it. He doesn't seem to have any significant ties to the Chroma Conclave incident, except that Ripley used it to convince him to turn on Vox Machina.

Orthax was an agent of the Raven Queen.
Orthax, the big, scary beak-faced shadow monster that haunted Percy's dreams shares a frightening number of similarities to the Raven Queen in the current arc. For example, the way that they approach their charges via confusing dreams, appearing as shadowed figures. While this could simply be imagery on Matt's part, I think it goes deeper. Think about Vex's summary of the Raven Queen's beliefs in episode 48. She hates those that cheat death, even especially listing Vampires as a subject of her ire. Who was the major driving force in creating "The List" and driving Percy to kill said vampires? Orthax's motivations for using Percy as an instrument of vengeance was extremely unclear. Did it simply seek to corrupt a man into falling to the dark side or was it something more? With this in mind, let's get a little deeper. From what we've seen, it takes significant effort for it to manifest in physical form, and even then it was still bound to Percy's shadow. It's possible that Orthax simply couldn't manifest physically without some kind of conduit or summoning, so it'd need a vessel to manipulate into doing his dirty work. After all, if it was a servant of the Raven Queen, what better way would one of her champions behave if not like its patron? This isn't even getting into the fact that it had a bird-like face, something extremely odd for a shadow demon in D&D lore (though perhaps not in Matt's setting). The Raven Queen is a Neutral-aligned deity, so she can have worshipers and servants that are both good and evil, so it's not a far cry from this being possible.
  • Jossed. Orthax is a demon that later made a pact with Dr. Ripley to help refine her gun work in exchange for killing Percy. Her gun was even a pepperbox, and it functioned just like The List. Also, the Raven Queen took her position as a deity to ensure that souls would reach the afterlife undeterred. Given that Episode 69 confirms that Orthax is consuming the souls he steals, the Raven Queen would be repulsed by Orthax.

Raishan will try to "collect" Percy as one of her trophies for her horde.
Covered in more detail here, but the long and short of it is that green dragons enjoy controlling people of great influence and status. Percy is not only a member of Vox Machina and a noble to boot, but he's also impressed Raishan with his intelligence. In Episode 74 he seems to think Raishan even trusts him to a certain extent, implying that she would let him cut off a piece of her to send to Thordak. These two have a very interesting relationship of conflict and mutual respect, and at this point Raishan might see Percy as a magnificent prize. Time will tell if she can craft a deal powerful enough to tempt him.

The Chain of Returning is just... a chain.
Grog can attach the Chain of Returning to one of his weapons, and this allows him to throw the weapon and then pull it back to him, letting him make multiple attacks a round. How is that not something an ordinary chain can do?
  • Jossed: In the fight against K'Varn the chain stops functioning magically as it is thrown into the beholder's anti-magic field. While a regular chain could do the same thing, the chain of returning just makes doing so easier.

Taryon Darrington is interested in guns, and will butt heads with Percy over them.
There's a decent chunk of evidence towards this:
  • The group finds him in Ank'harel, the last location of Dr. Ripley - the only non-Percy source of guns in Exandria - before her death at Glintshore.
  • It seems likely that he is an Artificer, an Unearthed Arcana class with two archetypes... one of which is a Gunsmith.
  • While it could just be a slip-up from Sam, Taryon mentions guns while talking to Vox Machina before correcting himself to refer to swords instead. If that's in-character, it seems suspicious.
  • A bit of a stretch and unlikely to be intentional, but "Darrington" is not too far off of "derringer", a type of pistol. "Remington" is an American firearms manufacturer.
  • Sam has previously had Scanlan carry a gun, and though he never did anything with it, it does show that he's already interested in them. And he's definitely proven himself willing to fuck with the party.

The next major antagonist will be the Elder Brain from underneath Kraghammer
After killing K'Varn, Vox Machina did a sizeable chunk of physical damage to the Elder Brain, rather than just focusing on fleeing. If the Elder Brain also decides it wants to eliminate firsthand knowledge of it and its colony from the world at large, that puts another set of crosshairs on Vox Machina's back.
  • This may depend on how quickly VM deals with Hotis and some other dangling threads (e.g. Scanlan or Raishan's research), since it is this troper's belief that the Final Boss will be Vecna.

Scanlan Shorthalt will not make another appearance in Critical Role
Scanlan's story is pretty much done. He came from nothing, he had parental abandonment issues. His father is either not alive, or just left him, and his mother died in a goblin attack. He abandoned Kaylie, but reunited with her. He has accomplished all that he set out to do, and gained a daughter in the process. What else is there for him to do while with Vox Machina? His life has come full circle.
  • Jossed: Scanlan does come back in Episode 99, with a new character arc for himself, how to win the trust of his former companions.

Percy's memories of his family's death are not accurate
Either Percy is traumatized, being manipulated by the odd smoky creature who offered him revenge, or just insane, but he describes his memories of the murders as "fuzzy." It's possible that Percy was either somehow culpable, or that the Briarwoods were not the actual villains, but either way, what happened to the de Rolos was not so simple.
  • Jossed. Percy may not have known why or how the Briarwords tricked his family into the position to be massacred, but he was traumatised, not delusional.
  • His memories may be inaccurate though not regarding the Briarwoods' culpability. The dream narrated by Matt indicates Percy saw the bodies of at least some of his family, but that's a dream and he does interrogate Desmond the carriage-boy to find out if any of his family still live, suggesting he's not certain and/or wants external confirmation of his memories - meaning he perhaps doesn't trust his memories, or is simply holding onto hope. Due to time and trauma - he's described as wandering in a haze after the attack - and that he was tortured, it's likely his memories of what happened are hazy and imprecise, or even that he's forgotten. Percy says as much: "There are some things you just forget."

The second Horn of Orcus is beneath Whitestone.
So Sylas Briarwood is a vampire, and Delilah might either be a Lich or a necromancer - at the very least, both of them are very well acquainted with the undead. The carriage driver's story indicates that the entire de Rolo property has been covered in a strange green mist, and that undead servants roam the halls. We also know that the Briarwoods have been feverishly digging for artifacts beneath Whitestone, as well as interrogating the family members - in Percy's words, "asking questions about the castle." If the second Horn is a long-guarded de Rolo family secret, it would make sense that Percy wouldn't know anything about it; he's the third child, and explicitly says that his brother and sister, Julius and Vesper, handled "matters of court." Not to mention there's the smoky entity that offered Percy vengeance for the deaths of his family - perhaps it is one of Orcus's godly opponents, attempting to stop the Briarwoods from accessing the horn.
  • While as of Episode 34 there's been no sign of the horn, the Briarwoods seem to have constructed a temple to Vecna in order to summon some dark force into the world. Vecna, being first a necromancer and eventually a lich (and in some planes an actual god), it is possible this theme of undeath will link back to Orcus in some way.

Cenokier's wife was killed by a dragon, maybe even Thordak himself.
When asked about Thordak Cinokier's first reaction is to ask that Vox Machina keeps him away from the fire plane. He states that he "doesn't trust dragons" and ask Vox Machina to take care of his wife's funeral arrangements. He also knew where Thordak spent most of his time while on the fire plane. It could be that the mention of the Cinder King bought those memories back to the forefront of his mind, and he decided to do away with his wife's ashes now that a group of heroes unknowingly said that they would take down something that, if not his wife's actual killer, would have been something of a reminder of her death.

The Spinning Orb of Death doesn't just suck up magic and objects, it sucks up information.
When she brought it forth, Lady Briarwood was working on behalf of Vecna, God of Secrets. Since the arcanist NPCs's research shows that it doesn't so much suppress or negate magic as absorb it and send it... somewhere, it would seem likely that that "somewhere" is "wherever the heck Vecna is". Being the God of Secrets, could learning things, especially things people want to keep hidden from others, help him as much (or more!?) than absorbing magical power? And if so, what perceptual powers does it have? Can it hear? Can it see? Can it read minds?

The Deathwalker's Ward armor was originally intended for Percy.
Most of the vestiges found by the party are pretty obviously aimed at a specific character: Fenthras is a bow, and Vex is VM's only archer); Mythcarver boosts two staple abilities of Bards (such as Scanlan); the Plate of the Dawnmartyr is heavy armor which (at the time) only Pike used; the Spire of Conflux boosts spellcating, can cast elemental magic, and has a history heavily associated with Druids, tying it at least thematically to Keyleth; the Titanstone Knuckles boost strength and size, which Grog relies on more than anyone; Whisper is a throwing dagger and describing tossing daggers is literally a catchphrase for Liam/Vax.

This leaves Cabal's Ruin and Deathwalker's Ward: the former might have been originally conceived with Tiberius in mind, since its absorbs magic for the wearer to use and Tiberius was pretty cavalier about about using his magic.

That leaves Deathwalker's Ward and Percy. Matt may have intended for it to set off story elements involving Percy's Nay-Theism, possible atonement for empowering Orthax, and his having invented a new and exciting way to kill people in general.

Percy's carelessness with that trap may have drastically altered not just the twins' story arcs, but his own. (And probably saved Cabal's Ruin from the cutting room floor.)

Vex'ahlia was a changeling
Fae are well-known for being obsessed with making deals. Vex'ahlia is also extremely secretive (and secrets are considered a form of currency in the fae realm), very closely connected with nature, and often seems uncomfortable with the world, as though she doesn't quite fit right.
  • If this was the case, you'd think it would have come up during the Feywild arc - at the very least, Shaundor would have used it to manipulate her.

K'ryyn wasn't the drow's real name.
Campaign 2 has made much about the drow Empress Leylas Kryn in eastern Wildemount's Xhorhas. K'ryyn showed up hired from Wildemount (specifically Deastok, in western Wildemount's Dwendalian Empire), and the name is similar enough that K'ryyn is likely an agent of the Kryn either under a false name or a highly corrupted spelling.

The further life of Gilmore post campaign 1
At the end of campaign 1, we got a good idea what the further lives of all the main characters would look like. But there was no information about Shaun Gilmore, and some fans were disappointed / bewildered by that. He hasn’t shown up in campaign 2 either (yet). So here’s my suggestion for a reasonably Happy Ending for Gilmore (and Jarett, and J’mon Sa Ord):

(Feel free to discuss the canon-compatibility of the following. I’m still not through with the entire first campaign and may be missing some details.)

After Vox Machina told Jarett to keep an eye on Gilmore, they started bonding off-screen - perhaps with Jarett assisting Gilmore in his daily magic ritual to strengthen the illusion protecting Whitestone. (So Jarett wouldn't feel so useless to protect the city anymore, and Gilmore wouldn't have to shoulder all the strain on his own and wouldn't need to Cast from Hit Points anymore.note ) Then a few days after that, Jarett really came to admire Gilmore for the man's bravery and competence in the fight against Thordak (especially comepared to how Jarett himself fared in that battle), and they found that as expats from the same culture, they had a few things in common, like missing spicy food.

A year or two after the first campaign ended (after building permanent teleportation circles to Syngorn and Ank'Harel, which takes a year of daily spell-casting), Gilmore decided to go back to Ank'Harel - his elderly parents clearly have money troubles (they were barely able to afford enough water when Vox Machina met them) and he hasn't seen them in 15 years; Whitestone is too small a city to support much of a customer base for a specialized magic shop, Emon and Westruun will need a long time to rebuild before it's worth operating an expensive shop there again, and Gilmore never liked the religious zealotry of Vasselheim's population; and Percy needs an ambassador to Ank'Harel to organize the residium trade that he promised to the Crystal College. Jarett decided to go with him, now that his criminal record has been cleared by Vox Machina pulling strings, perhaps also to see his own relatives and to help Gilmore rebuild his shop there. (I'm assuming that Gilmore originally went to Emon because there was too much competition in Ank'Harel for a young, low-level magic item creator to get a foot in the market, and because the snobby foreign wizard enclave that is the Crystal College wouldn't accept a local peasant boy who developed his magic purely through raw talent and creativity, not through scholarly training. But by the end of the first campaign, Gilmore outclasses most of them and he would like to rub their noses in it.)

(No, there has never been any hint that Jarett is into guys as well, but when has that ever stopped slashers? Besides, there was no indication that he was opposed to the idea, either. And at least it’s reasonable to assume that they have enough things in common to form a bond, which is more than Pair the Spares couples are usually based on. And who else are you gonna let Gilmore find some happiness with? There is exactly one writer on AO3 who thought Taryon/Gilmore was in any way likely.)

I don't think this would be a true love for the ages - more "storge" than "eros". And I think they would eventually break up because Jarett realizes in middle age that he wants children after all. Or perhaps he falls madly in love with some woman on his travels to get spell ingredients for Gilmore. Or maybe they agree to an open relationship due to the long periods apart and Jarett ends up accidentally impregnating a one-night-stand on such a trip and then wants to do the right thing and marry the woman to provide for his kid. Gilmore is not happy about it, but accepts it because he knew what he was getting into when he started dating a man who's 15 years younger than him and plays for both teams. Love doesn't always last forever - c'est la vie.

Unfortunately, your dating pool is very limited when you're in your 50s, gay, and living in a city that isn't culturally homophobic, but still only has a few thousand inhabitants (as medieval "cities" normally did), only about 5-10% of which would be male and queer, and at least a third of those would still be children.

But now that Gilmore is unattached, J'mon Sa Ord suddenly starts courting him, because they think it would be a shame to let his innate magical talent (he's a rare "Runechild") die out with him and lose it as an asset for the city. Gilmore is flattered, and he's long thought that (good) dragons are sexy, and after all, he's always had a thing for slender guys with long hair. Devo'ssa the dragon is actually physically female in my headcanon, but in their humanoid shape they are androgynous and can alter their physical details to anything Gilmore would be comfortable with, so that's not a problem. They have a clutch of quadruplets or quintuplets together (hatched from eggs). And while they agree that J'mon will be the kids' mother and father (what with the human Gilmore not having enough years left to raise a bunch of half-dragons to adulthood), Gilmore is still a part of their lives as the fun uncle who gets to spoil them rotten. And the more than 400 years old dragon turns out to be quite the interesting person, a charming conversationalist, and sexually rather... creative in the way only shapechangers can be. So over time and through the close association brought on by having children together, Gilmore and J'mon bond and maintain a contented relationship until Gilmore's death.

Casting for the eventual Live Action Adaptation

Bertrand Bell really did do all of the things he boasted about
  • It's played up as something akin to Harry Potter's Lockheart, with Bertrand stealing credit for killing various monsters under "an assumed name." But- he is a fairly skilled adventurer, able to tag along with Vox Machina and not die, and he's a Cowardly Lion who managed to rescue Percy's arm all by himself.
    • So, without any real evidence to back it up, my theory is that Sir Bertrand Bell went by a different name in his early adventuring career. Maybe he was more selfless and humble, seeking to do good rather than just earn glory and riches like Taryon Darrington. But good deeds don't pay the bills, so he rebranded himself as part of a marketing campaign.

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