Simon Roswell

Simon Roswell
Simon Roswell is currently serving as a Lord of Volkachin underneath Chancellor Elton DeCashe and Grand Marshall Wynne DeCashe. He is also known for his participation in the fight against Pilut in 946 P.L. alongside the other members of his party, Bug and Ranulf. Although still relatively new to his position as politician and spy, Simon has found himself flourishing in Volkachin.

Early Life
Very little is known of Simon's early life. He did reveal to the party that he was born under the name Charlie O'Malley, but the reasons for his name change are unknown. Simon commonly makes reference to those around him of his being like the wind, whatever that means. It is assumed at some point in his early life, he figured out how to use magic and began his life as a wizard.

At some point, Simon left home in order to pursue his career as a snake oil salesman young entrepreneur. Due to his oddly charming persona and blossoming talent in illusion magic, he seemed to achieve mild success at this as he was able to supply for himself and many of his heightened luxuries. However, ultimately his desire for fame caught up to him, and he was no longer interested in being a measly merchant.

Simon became involved with the lord of some city briefly when he was around eighteen years old. He has not disclosed much about this relationship other than that it dissolved and the two men went their separate ways.

Joining the Party and Living in Blue Field
Simon's chase for notoriety landed him a partnership with Bug and Ranulf. After fighting their way through a cave, the party obtained some treasure, including a deed to a manor in Blue Field. In Vinstok, Simon opens an account at the nearby bank and makes a connection with Miguel. In Blue Field, the party found themselves living in a haunted manor previously owned by some mysterious adventurers who went missing while hunting a Mindflayer colony. At the manor, Simon lived in Wyatt Crayne's room. After slaying the ghost of a Gelfling child named Jo, the haunting seemed to end. There Simon found some documents from Crayne himself detailing Illusion and Enchantment magic, particularly the spells Crown of Madness and Fear, but after years of research, Simon is still unable to decipher most of it. Simon also had the idea to found a rowing team in Blue Field.

Also in Blue Field, the party meets Aristrada, a strange mermaid-like woman who lives in a lake. Aristrada soon becomes an important figure to the party. Simon isn't interested in going into her cavern at first, leaving Bug and Ranulf to go to her alone to de-age themselves.

Their initial time in Blue Field is short, however, as the party becomes involved with other matters around Reixila.

Altokiv
Upon entering Altokiv, Simon is given a necklace marking his position as an Arcanist. He is not happy about this, but he keeps the necklace on to avoid trouble. When the party hears of a wood elf wanted by the Qavala, Simon is interested in killing him for the bounty, but Ranulf and Bug dissuade this idea. In Altokiv, Simon researches the Crowned Comet, finding out that it is best viewed in Ashmonte and occurs on the day of the solstice.

During Bug's fight in the Blood Bowl, Simon is wary of the increased amount of Tribunal around. He and Ranulf leave after unsucessfully trying to convince Bug to come. This is when an Ebyrith attack occurs in Altokiv. The party is able to escape Altokiv with the help of the half-vampires who invite the party to the Pillars.

While researching the Eluvian in a library outside of Altokiv, Simon meets Rosalka, a young girl also researching the Revari. She tells Simon some troubling news: the Arcanist's Alliance may be turning Arcanists into Ebyrith. She shows Simon a poem about the Eluvian that refers to it as "a terrible glass." Outside of the library, the party meets Stevie-6, Rosie's mechanical bodyguard.

The Pillars
After meeting with Rosie, the party decides to scope things out at the Pillars. When they arrive, they see a crowd of mages in gray robes transfixed on these pillars where a spark of white lightning is bouncing around. There is a ritual and then a blast of great white light. Simon feels a rush of power as the light expands throughout the land, something that troubles him.

Upon speaking to the half-vampires again and meeting the supposed leader Pilut, Simon is informed that he will be turned into an Ebyrith. Simon is very against this but continues the awkward conversation anyway.

Simon tries to speak to a mage through Message, but the mage is unresponsive. They all seem to be under some sort of influence. Ranulf restores one through ''Lesser Restoration. ''After telling them that DeCashe is not involved in whatever is happening with the half-vampires, the party decides to try to find him.

Meeting DeCashe and Wynne
In Blue Field, the party meets with Aristrada who tells them that DeCashe did come to her, but she is not allowed to say why. She does tell them, however, that he is holed up in The Faerie's Tits.

The party meets DeCashe in the tavern, but when they try to explain what is going on, it seems as though he cannot hear them. He introduces the party to his wife, Wynne and the rest of his entourage. After a bit of going back and forth, the party realizes they cannot convince the Arcanists of the severity of what is happening outside of Blue Field and head back to Aristrada.

The party is able to convince Aristrada to release her hold on DeCashe and his crew, but they still seem uninterested in helping until Simon mentions that they have a lead on the Eluvian. DeCashe and Wynne ask the party to retrieve their memories, and after another visit to Aristrada who reveals her true identity as an Aboleth named Labe, they are able to get their memories back.

Simon is flushed away. It's traumatic. He meets Fozzie Bear.

Simon meets back up with the party as they make their way to Onmire to slay the vampire lord father of the half-vampires in order to make them mortal. They also must look for the Eluvian.

Onmire
While following the meteors, the party eventually runs into a temple of Yaramaz. Outside of the temple, they have a scuffle with two drakes named Jethro and Cletus. It is revealed that the drakes belong to Queen Laveaux, the ruler of Onmire. She warns them about the dangers of the temple and wishes them well.

Before entering the temple, the party is intercepted by Wynne who tells them that DeCashe sent her to steal the Eluvian from them. She tells them that she does not want DeCashe to possess the Eluvian. Posted outside the temple, she defends the temple from prowlers.

It is there Simon meets Shotgun the Elf, a halfling who apparently once shotgunned an elf. Simon does not like this.

Also in the temple, Simon also is exposed to Revari magic for the second time when he is possessed by an Ebyrith from the Eluvian after killing Izatlol. He grows whiskers and inflates. He hates it. However, he does learn that when possessed by this particular Ebyrith, he retains some control of his body.

Outside the temple, Simon learns from Stevie-6 that the "Ebyrith" in Altokiv were illusions. It is at this time Simon begins to suspect Crayne may be involved as he was researching Illusion magic before his disappearance. Simon fails using a scroll of Teleport that Wynne gave him. Oops.

The Party Returns to Reixila!
After Wynne leaves, the party decides to pit stop in Vinstok. Simon visits Miguel and asks him out on a date. The banker accepts, and the two go to Osbey's Crosby's. Simon does particularly well charming him and follows him back to the bank. It is there Miguel reveals his status as a dragon and threatens to eat Simon. Not as scared as he should be and far too horny for his own good, Simon tells him where the Eluvian is to avoid getting eaten then the two...fade to black.

Upon meeting back up with DeCashe and Wynne, DeCashe reveals that he knows Simon told the dragon about the Eluvian and that the two were intimate. Weird, but alright. The party discusses if they will help the Arcanist's Alliance or not. They say they will, and then Ranulf performs a rendition of a song where he tells DeCashe of Wynne not wanting him to have the Eluvian. The party dips.

They head back to Altokiv where Simon is given handcuffs that completely block his magic. They tell Rosie of the Eluvian. It is then the party begins tracking Tavra.

The party also break into Vino's bank. Simon finds a letter to Vino from Miguel that mentions a buyer for the Eluvian. It also mentions Simon, as Miguel mentions that Henri would really like him. To eat. Oof.

Arriving in Valley Grove, Simon receives the spells Sending and Feather Fall. He also reveals his distaste for Wood Elves.

Voyage to Volkachin
Simon begins discussing saving Wynne from her terrible marriage to DeCashe. He suggests "Gone Girling" her. He also hires a bard, Clem, who leaves when things start getting dangerous on their journey.

On the Riverboat Chaarlie, Simon participates in the various fights the party gets into. In one particular fight, Simon must hide in a pickle barrel. He also tries to catch some rays, but because of the dense foliage of Onmire, he is unable.

In Royeaux, Simon enjoys himself among the upper class of the big city. He buys a heroin needle from Popeye and suggests to the party that they network. Ranulf asks Simon if he is a psychopath, a question that perplexes Simon. Simon meets a demon named Kovref and has a brief affair with him for the night.

Also in Royeaux, Simon buys two small mirrors and also fashions two platinum pieces into earrings. He also obtains the spell Fireball.

Simon also finds out from Queen Laveaux that Wynne had been previously married to a Tanari demon.

Volkachin and Slaying Tavra
Simon enjoys the incredibly mage-friendly Volkachin. When they meet the Harbinger and are launched into the plane of magic, Simon has a bright garnet-colored aura around him. He is particularly amused when the Harbinger shows the card the Fool for DeCashe. Simon is startled by meeting Crayne there and offput by his Ebyrith-like appearance.

When DeCashe and Wynne appear through a portal in Volkachin, Simon is able to get Wynne's attention. He is  upset to hear the news of an impending Arcanist genocide that King Olvman is planning. Simon suggests that Pilut is the new pupil of the Revari.

After a tumultuous experience in the abandoned Tribunal castle, the party is able to obtain a pair of magic-nullifying handcuffs. DeCashe summons them to the castle in Volkachin that night. Simon suggests that DeCashe is in love with him based off of no evidence at all. At the castle, the party meets Meredith who Simon tries to set up with Ranulf. She tells the party that Wynne is in the red-light district of Volkachin, news that very much interests Simon. After seeing her feed off of some women then Revivify them, Simon tells Wynne of the Grand Paladin. She mentions that she is leading a strike force against Pilut and leaving Volkachin.

On a ship to the Titan Isles, Simon reveals his previous engagement to a lord while dodging questions about his childhood. Upon arriving on the island, the party is able to easily dispatch Tavra. However, during the fight, Simon experiences Revari magic through Tavra who reduces his Intelligence. This does reverse after Tavra's death, but it is a reminder to Simon of the power of the Revari.

"Rescue" by the Qavala
Simon falls into a deep slumber after Pilut's attack. While asleep, he is transported into the Plane of Magic where he is surrounded by Ebyrith. However, instead of being consumed, Simon is protected by a creature like the Harbinger, and rings of runes form on Simon's arms.

He wakes up and is informed of the Qavala's intention to bring them back to their homeland and assimilate them into their culture. Simon requests "Boy King" as a job. Simon is able to successfully convince a Qavala Rescuer by the name of Corn to give him back his Arcane Focus while Bug slips in and retrieves the party's belongings.

After the party escapes from the Qavala ship, Simon receives a message from DeCashe stating that he has left Volkachin because Wynne has gone missing. Simon casts Sending to Wynne who subtly tells him that she is trapped in Tzopilotl with A'kord watching her. Upon hearing this, Simon smugly sends a message to DeCashe who reveals he already knew.

DeCashe teleports the party to New New Iberia where the party plans their next step. Simon wants to rescue Wynne, something DeCashe encourages but mentions he cannot participate in, which Simon uses as ammo to suggest DeCashe does not care for his wife as much as he should. After Simon harasses DeCashe more, trying unsuccessfully to poke him with a heroin needle and give him chicken fries, DeCashe teleports them to the coast with a rowboat.

Before embarking to Tzopilotl, the party is intercepted by Stevie-6 who brings them to Cliffguard to meet with Rosie who is experimenting on Ebyrith. Simon suggests trying to lure Pilut to Cliffguard to off-put his magic and capture him, but Rosie states that it is too dangerous.

While going through the half-vampires' manor, Simon finds some spells in the library. He tears a page out of an ancient Revari book activating some Book Golems. In the same manor, he is nearly killed by an undead.

The Fight with Pilut...and the Aftermath
Simon's role in the fight with Pilut is largely support. He faces a near-death when Crayne steps in with Ebyrith spiders that poison him. However, ultimately the party reigns victorious. After the fight, Simon is once again unsuccessful in casting Teleport, and Wynne flies off as a bat as the Tribunal meets up with them.

Simon is openly hostile to the Tribunal members in this interaction, still bitter from being marked and handcuffed by them. However, he faces no further problems with them.

Upon being summoned to the Pillars to testify before both the Arcanist's Alliance and the Tribunal, Simon suggests to the party that they use this opportunity to incriminate DeCashe. However, ultimately the party decides to tell the truth about their whole story...leaving out certain bits about the Eluvian.

t the Pillars, Simon wishes to step up with the Arcanist's Alliance but decides to walk up in the impartial middle with Bug and Ranulf. During his testimony, he fluffs the story up a bit and tries to scare Wynne and DeCashe by nearly speaking about the Eluvian. However, Simon's testimony is cut short by the return of Tavra.

In this scuffle between the incredible Ebyrith awoken by Tavra, Simon makes the decision to help Wynne and DeCashe much to the distaste of Ranulf. Bug reluctantly joins him. Several times throughout the fight, Simon brings Wynne back up from being unconscious through his potions. When they slay their Ebyrith, Simon, in a move that solidifies his place in the Arcanist's Alliance, continues fighting alongside the mages while Bug flees and Ranulf escapes with Rosie and Stevie-6.

The Five Year Gap: Simon's Political Awakening
After the fight with the Tribunal, Simon returns to Volkachin where he is made a lord by the newly crowned Chancellor DeCashe. He is given a good portion of land and political prestige. When given the choice between becoming a fully fledged politician or fighting alongside Wynne, Simon decides to stay in Volkachin.

Despite the terrible poverty crisis facing Volkachin, Simon becomes renowned for his very extravagant parties. He throws these parties both for his own amusement but also in an attempt to keep morale high. Once a year, on the anniversary of Pilut's death, Simon throws a grand festival to celebrate.

DeCashe's institution of a Spell Tax as well as the lack of funding being sent to the countryside allows Simon to flourish in his place as a lord.

Alongside his political duties, Simon also serves as a spy for DeCashe. In one particular mission, he begins investigating Yunque, a man associated with Pilut. He gave Pilut instructions on how to craft more efficient Ebyrith. When Simon arrives at the man's office, the mages alongside him are revealed to be doppelgangers who attack him. After dispatching the doppelgangers, Simon begins being shot at by an unknown figure.

Reuniting with the Party
After rushing out into the streets, Simon ducks behind a melon cart, meeting Ranulf and Bug once more. He explains to them that he is being shot at. The party is able to duck into a cigar factory in order to talk about what is happening.

Simon reveals his status as a Lord of Volkachin, which directly contrasts Ranulf's position as part of Rosie's Council. Simon asks about Rosie's genocidal tendencies, and Ranulf asks about DeCashe turning mages into Ebyrith. Both are dumbfounded at the other's accusations. The two consider their positions but decide to work together to figure out who is attacking Simon.

After the party's initial encounter with the mysterious gunman, the party heads to the capital of Qolas where Yuan-ti have arisen after years of being dormant. They slay a few along the way, facing the gunman a few times, and upon their arrival, they find the city completely overrun by Yuan-ti.

Simon turns into one of the higher-up Yuan-ti and successfully gets the party into the main pyramid where they discover they must find keys to unlock the lower floors. After traveling to each part of the city, the party is able to get into the basement where they meet Yunque whose previous identity was that of the genie representation of Nifaq.

After being given access to three of the other eyes, the party decides to begin tracking the Colossai. The first is the Glutton who is in Qolas.

During the fight with the Glutton, Simon stays away from the massive creature and has a primary goal of keeping his concentration on Haste.

Faervane and the Artisan
Simon is initially cynical of Faervane as the first occupants he meets are a town of wood elves. He is not charmed by the woodsy Lincoln Log. However, as the party delves deeper into the country, Simon finds an appreciation in the chaotic beauty.

On the way to meet the Scarlet Lady, Simon is told by Stevie-6 that he has been banned from Reixila and charged with the crime War Profiteering. Simon is not surprised by being banned from the country, but he is amused by his charge.

When prompted by Ranulf if he thinks the two should try to save the Scarlet Lady or help the werewolves, Simon, despite leaning toward helping the werewolves, states that it is Ranulf's choice. During the fight with Brieuc, Simon realizes that the werewolf is under the control of Crayne.

After Brieuc's death, Simon and Ranulf descend into the cave to find the Scarlet Lady. Simon uses his magic to break the chains containing her. It is Simon who comes up with the idea of making Lincoln Log the King of the Werewolves to serve as an ambassador for the Scarlet Lady, a proposition both parties accept.

From the Scarlet Lady, Simon receives a boost to his Wisdom score.

Within the Underfae, Simon uses Alter Self to turn himself into a drow in order to blend in. He has Ranulf and Lincoln pretend to be his slaves (Pork and Beans), and Ranulf Polymorphs Bug into a small cat. In the art exhibit, Simon becomes transfixed by a Revari ring, making the internal promise to steal it.

During the fight with the Artisan, Simon does well avoiding hits. However, he does get hit once by the Artisan's acid breath, severely weakening him. When Sivil and Aayla attack, Simon is messaged by DeCashe, stating that Arcana Land is opening next week, and he needs to know if Simon wants fro-yo. Simon wants fro-yo.

Simon lifts Ranulf's corpse after the fight, stating to Bug that the two should bring him to his hometown to be buried. After making Lincoln drag Ranulf's body in a coffin the whole way back to Fionna's Hill, Simon announces to the Gelflings of Ranulf's death. Simon says a few words about Ranulf's bravery and good heart during the funeral.

When Ranulf returns from the dead, and Bug and Ranulf decide to Reincarnate Sivil, Simon sits out of that interaction. When she is returned as a Warforged, Simon is confused on why that is such a bad thing.

Outside of Faervane, Simon is the only one to not leave a note on Brieuc's reincarnated body.

Return to Volkachin
Simon uses Sending to DeCashe to see if Ranulf can come with him back to Volkachin on the way to the next Colossai. DeCashe agrees but states that Ranulf will be properly monitored.

On the way, the party stops in Craven's Rest where Simon uses his political status to access some documents about Crayne. There he finds out about an explosion of energy during the party's venture to stop the Mindflayers. The party goes to that area, but Simon is deterred by the anti-magic field and the ring screeching in his pocket.

At the gates of Volkachin, Simon's excitement at returning to his home increases. He lightly chats with the guards and reminds them to not hurt Ranulf. They say they will not, and that all they will do is keep an eye on him.

Upon entering the city, Simon's politician emerges as he begins chatting with the citizens, displaying his remarkable memory about their lives. It becomes clear that the commoners adore Lord Roswell, but the nobles do mock him a bit.

Simon shows off his manor which is conveniently located across the water from DeCashe's. His manor is elegant and contains many portraits and statues of Simon. One particular room of note is one Simon calls the "Red Room."

It is in Simon's manor that the party meets Squiggly, Simon's steward whom Simon adores. Squiggly gives Simon a note that states that he must throw a dinner party tonight, exciting Simon who is eager to show his hosting skills to his friends.

The party meets with the Qavala with the intention of getting across the frozen Bay of Oreleth. The Qavala reveals that they only take converts, not money. Simon takes mental note of this with the intention to return later.

At the dinner party, Simon's odd dynamic with DeCashe is put on display. The two go back and forth, mocking each other with the support of their own men. At one point, DeCashe refers to Simon as his protege which Simon does not like.

When Wynne arrives, while everyone else in the room becomes nervous, Simon is excited to see his friend again. During the dinner, the party notices Wynne's clutch on DeCashe (and gets a kick out of it). After leaving the table, Simon follows the two into the gardens where he shows them the Revari ring. Wynne warns him to not let it touch his skin and takes it with the intention of researching it. Sending DeCashe away, the two speak in private. Simon mentions that Ranulf is not fully with the Tribunal and may be able to be manipulated into departing from Rosie completely. He also suggests that if Wynne has anything up her sleeve, she should enact it while Ranulf is away in the middle of a frozen bay. Wynne seems to like this suggestion. She also requests that Simon try to get a vial of the Ebyrith cure from Ranulf.

The next day, Simon and his friends go to DeCashe's manor to find out about the picture room. Simon attempts to sit on one of the armrests of DeCashe's throne, but he is pushed off by the unamused Chancellor. he takes a seat on his desk instead. After more back-and-forth between the two Wizards, while DeCashe does not show Simon the picture room, he does show Ranulf and Bug.

Simon returns to the Qavala and tells them that by killing the Colossus, the party will be helping the Qavala get more converts. The influx of money Volkachin would receive from the decimation of such a large distraction would only make Volkachin's rich richer and the poor poorer. The wealth disparity will become worse, and the people more desperate, meaning more converts for the Qavala. The Qavala man agrees to accept gold in the place of converts.

Simon approaches Wynne on her ship, asking her to help him convince Ranulf that she spoke to the captain and not Simon. She agrees and helps him secure a ship.

During the opening of Arcana Land, DeCashe prompts Simon to give a speech for the opening day in an attempt to fluster him. Unhindered, Simon tells the people that he knows they don't want to hear a long, boring speech and instead encourages them to open the gates for the fun to begin.

At the theme park, Simon mostly stays by Wynne's side. He gets vampire face paint, and the two ride several rides together. She tells him that she has brought the ring to the Harbinger to help decipher what it is. Simon asks her to please tell him what it is no matter what, even if it is something terrible. She says she will.

Journey to the Bronze Eye
After leaving Volkachin, the party found much difficulty in making it to the presumed location of the Bronze Eye. The perpetual, unyielding storm over the Bay of Oreleth made for an inability to sleep on the ship. Simon found some success in using his Tiny Hut, but it was only useful for sleeping at night.

Noticing a compression on Bug's chest, Simon cast Blink to discover Sea Hags tormenting Bug in his sleep. He was unable to kill the hag but scared her off long enough for Bug to sleep.

When a mysterious woman appears to the party, Simon is the only party member that considers her offer. He ultimately declines at the behest of his party.

During the first interaction with the Warrior colossus and his army, Simon expresses reluctance in jumping into the frigid water but ultimately joins Orca Ranulf and Bug in diving below the surface. Hearing of the sleeping giants, Simon and the rest of the party agree to help them defeat the hags.

While moving around the Qavala mine in an attempt to find a way around the Wall of Force blocking their path, the party runs into a sea dragon. Simon tries to trick the dragon with his Mislead spell and finds some success disorienting it. The party escapes through the way they came. Simon snags a Disintegrate spell, allowing the party to proceed past the Wall of Force.

After making it into the lair after some trouble navigating the puzzles in the Qavala mine outside, the party meets up with the hags within their lair. After witnessing a short conversation between the hags and Crayne, the party watches as an Ebyrith is summoned past the Wall of Force they cannot get past. Simon sets up a Tiny Hut to shelter the party while he regains a spell slot to cast Disintegrate. This tactic proves futile, however, as the hags attack ethereally. During the attack, Simon makes the mistake of Blinking during the fight only to be nearly killed by the hags. The fight eventually swings in the party's favor, and they are able to successfully kill the Ebyrith. However, one of the hags escapes.

When the party realizes the Ebyrith was actually their old acquaintance Kenny G., the party sees firsthand the terrible process of being turned into an Ebyrith. The asleep Tribunal and arcane prisoners in the cells of the lair provide a dilemma for the party. Simon says he will arcanely try to detect if they could be saved from the Ebyrith process. He does not see any sign of any Ebyrith inevitability but lies to the party and says the prisoners are too far gone. Despite wanting to kill the Tribunists, he instead kills the arcanists, albeit viciously.

Simon is able to avoid the dead ends of the lair by Blinking through them. He ends up in a library first where a spirit communicates through him, having Simon write copious Revari writing. Simon is mentally affected by this, gaining both a drinking and killing habit. He also finds a Tarot card deck with cards painted in the likeness of those the party knows. He makes a point of laughing at DeCashe's Fool card.

In one of the hag's rooms, Simon finds a cum jar. He pockets it.

After successfully completing the potion required to awaken the giants, the party returns to the Mouth of the Abyss where the giants are awake. The giants believe that the apocalypse is inevitable, but Simon leads the charge in convincing the Queen of the Sunken Guardians to at least check things out above the sea before disregarding the cause totally. She agrees, and she gives the party the Bronze Eye.

Relationships
Because of Simon's narcissism and mild psychopathy, ''Simon rarely makes anything other than a superficial connection with others. However, as Simon has become closer to those around him, he has been able to create some dynamic relationships with both the other PCs and NPCs.''

Bug
For the most part, Simon finds Bug to be amusing. Bug is definitely the member of the party Simon gets along with the best, largely due to the two being more laid back than Ranulf. He also appreciates that Bug helped him in the fight at the Pillars and holds no ill will that he left him there.

Simon is currently unaware of his status as Bug's half-brother, but he does suspect that they are related. At the moment, he is pushing that thought to the back of his mind, considering O'Malley to be a common surname. He currently believes that the two are related by marriage or cousins at most.

Ranulf
At the beginning of the party's journey together, Simon found Ranulf to be annoying. Ranulf's stoicism often contrasted Simon's hyperactivity, leading the High Elf to often remark on Ranulf's ability to kill his mood. However, this dynamic changed when Ranulf performed his song for DeCashe and Wynne in DeCashe's manor. Since then, Simon has found Ranulf to be a funny and clever companion.

Despite Simon liking Ranulf, the two have one of the most discursive relationships. Simon's friendship with Ranulf is often a point of confusion for Simon himself who often cannot tell how Ranulf feels regarding him due to the dissociation between Simon and being able to understand other's emotions.

He genuinely finds Ranulf to be a good man with a good heart. While he is incapable of appreciating this, he knows that other people do. Because of this, he is happy to associate with him.

While apathetic to his death emotionally, Simon did feel an obligation to bring Ranulf to a comfortable rest in Fianna's Hill. He also felt an obligation to ensure Ranulf was not hurt in Volkachin, but this is likely due to Simon desiring for Bug and Ranulf to enjoy themselves there and more importantly, fully see how luxurious Simon's life there is.

Elton DeCashe
Despite the two being very similar in both personality and ambition, Simon cannot stand DeCashe. His hatred of DeCashe began with jokingly suggesting that Wynne was too good for him, but as time went on, Simon realized that he genuinely did not like him. The nail in the coffin of that potential friendship came when DeCashe began trading barbs with Simon. Most people are unable to keep up with Simon's banter, but DeCashe is a clear exception, something that contributes to Simon's fascination with him. It is assumed a large portion of Simon's dislike of DeCashe emerges from jealousy.

Even though Simon hates DeCashe, he has developed a sort of obsession with him. Within the five years spent in Volkachin, Simon became very enamored with the idea of surpassing DeCashe in power and elegance. The dynamic between the two Wizards was a source of entertainment for the citizens of Volkachin (aside from Wynne).

Simon's hatred and obsession with DeCashe is one of the largest motivations for him taking on the Colossi. The Elf believes that if he can take down the Colossi, it will give him the leverage he needs to surpass DeCashe.

It can be assumed Simon's fascination with DeCashe is influenced by his inability to connect with people on any deeper level. He secretly (and subconsciously) enjoys being around DeCashe because it brings him a connection unlike one he has ever experienced.

Wynne DeCashe
Simon's relationship with Wynne has changed fairly drastically over the course of the campaign. Originally, Simon found amusement in teasing her about her relationship with DeCashe and dramatically fawning over her. Despite referring to her as his "best friend" multiple times, Simon did not really care about her at all.

Simon began liking her as she began helping the party in their endeavor to take on Pilut. This is when he began to see that Wynne was stronger than he may have initially thought. When she was taken by the half-vampires and trapped in Tzopilotl, Simon wanted to save her (mostly to impress her).

Upon joining up with The Legion of Magi officially, Simon's opinion of Wynne changed. Instead of seeing her as merely an associate of DeCashe, he saw an incredible power in her. Simon's realization that Wynne could be the strongest player in the war as well as DeCashe's total submission to her made him want Wynne to be his ally. When Wynne's tone expressed that she was impressed he'd been able to take down a Colossus, Simon was genuinely pleased. While he still does not trust Wynne, he does trust in her ability to win the war which is all he needs.

Rozalka
Upon meeting Rosie, Simon found her to be charming. He was impressed by the girl's research, and when he found out of her nobility, her royalty. His relationship with Rosie before the Pillars was a good one with the two both liking each other. Simon also found her willingness to stand up to her dad regarding his position on mages admirable.

After the Pillars, Simon's opinion of Rosie's character did not change much. As he told Ranulf before the big decision, he had assumed Rosie would be manipulated by the Tribunal as soon as she took the throne. Unlike Wynne and DeCashe, however, Simon is not afraid of Rosie, likely because he cannot see her as anyone but the kind fourteen-year-old girl he met in the library outside of Altokiv.

Miguel
Simon's pursual of Miguel began when he made an account in Vinstok at the man's bank. He found Miguel to be handsome and mysterious, and the fact that Miguel did not instantly swoon over Simon created a challenge for the High Elf.

The fact that Miguel revealed himself to be a dragon planning on eating Simon did not deter Simon's attraction to him. If anything, it strengthened it. After telling him where the Eluvian was, Simon still continued their night, initiating a sexual relationship with the dragon. Afterward, Simon left, saw that he was leaving town, and has not seen him again since.

Simon's one night stand with the blue dragon is a source of pride for Simon. While he states that his time with Miguel was a long time ago and irrelevant now, he does want to see the dragon again and is still very attracted to him.