Allies
Egg Boiz
- "Not my little Egg Boiz. They do my evil bidding for me!"
- ―Sir Pentious, to Vaggie
Sir Pentious threatening the Egg Boiz
The Egg Boiz were Sir Pentious' minions. They are excessively sycophantic and seem to adore everything about their boss and seek for his approval. However, he has a tendency of abusing the Egg Boiz and be somewhat aggressive towards them whenever he gets annoyed.
Some of them are masochistic, shown when they are delighted by their boss' abuse, even hoping to get shot with his ray gun. However some of them would agree with Sir Pentious' enemies such as when Angel Dust insulted him and his hat and one of them acknowledged the roast Angel made. Sir Pentious would also say that his Egg Boiz are stupid.
Sir Pentious tearfully hugging his Egg Boiz
It is shown in "Scrambled Eggs" that Sir Pentious cares about the Egg Boiz since he didn't want to get rid of them but had to under Vaggie's orders. He spent most of the episode missing them and claiming he can't fight without them. Sir Pentious was also happy when Vaggie decided to give him back the Egg Boiz and he happily hugged them, but also ordered them to clean up his room. Sir Pentious even cuddles with them at night.
As shown in "Hello Rosie!", Sir Pentious typically ignores what his Egg Boiz say since they always say "insane shit", causing him to typically not take anything they say seriously. Following his sacrifice, one of his most loyal Egg Boiz, Frank, survives and honors Pentious at his memorial.
Hazbin Hotel staff
Charlie Morningstar
- "Thank you, Pen."
- ―Charlie, to Sir Pentious
Charlie gives Sir Pentious a second chance
Charlie is the first true friend Sir Pentious ever had. Iniatially, Sir Pentious considered Charlie an enemy during his two attacks on the hotel. Charlie was the first to welcome Sir Pentious into the hotel. At first, he only gained her trust to infiltrate the hotel under Vox's orders to spy on Alastor. When he was found out by the staff and Angel Dust, he was mocked and abandoned by Vox but given a second chance by Charlie. Her forgiveness and compassion compelled him to truly change and stay at the hotel for real. In a friendly manner, Charlie nicknamed Sir Pentious "Pen".
While spending time at the hotel, Sir Pentious formed a close friendship with Charlie, being considered part of her chosen family. Sir Pentious shares his innocence with Charlie, such as when they are horrified when they see Angel's porn movie and like her, Sir Pentious is sensitive to beautiful moments such as when he saw Charlie reconcile with her father Lucifer. In "Hello Rosie!", Sir Pentious and his friends, despite Vaggie's warning to leave because they were not looking to fight, decided to firmly stay at the hotel to help Charlie and Vaggie fight the angels.
Sir Pentious confides in Charlie, telling her about his feelings for Cherri Bomb and is inspired by her to try to confess. He was able to give his life for his friends, although at an apparent death, devastating Charlie and unleashing her fury against Adam. In honor of Sir Pentious' sacrifice, Charlie and her friends honored him with a painting of him as a general while renovating the hotel.
Vaggie
- "Get ready for them, Vagatha!"
- ―Sir Pentious, to Vaggie.
Sir Pentious is reprimanded by Vaggie
Sir Pentious considered Vaggie an enemy during his first attacks on the hotel. To infiltrate the hotel, Sir Pentious pretended to want to redeem himself, despite the suspicions of Vaggie, who saw Sir Pentious as useless without his warship. After discovering that he worked for the Vees, Vaggie and Angel Dust decided to kill him, but Sir Pentious was given a second chance by Charlie, convincing him to truly want to redeem himself. However, Vaggie judges Sir Pentious' steampunk inventions.
During his first week, Sir Pentious was distrustful of Vaggie and the others, motivating Charlie to teach Sir Pentious to trust them. He became annoyed and saddened when Vaggie ordered him not to bring weapons to the hotel and to get rid of the Egg Boiz. After being in a turf war, Sir Pentious gained Vaggie's trust and friendship, and she allowed him to keep his minions.
During the battle against Adam's army, Sir Pentious helped Vaggie on the battlefield and called her "Vagatha". When he was vaporized by Adam, Vaggie was among those that honor his sacrifice at his memorial after the hotel's reconstruction.
Niffty
- "The bad boy is back!"
- ―Niffty, to Sir Pentious.
Sir Pentious is jumped on by Niffty
Sir Pentious considered Niffty an enemy during his attacks on the hotel. Initially, Niffty was attracted to Sir Pentious, as he was a "bad boy", something that disturbed and made Sir Pentious uncomfortable due to Niffty's advances, but after agreeing to join the hotel, Niffty became disillusioned with Sir Pentious. After lessons in trust, Sir Pentious began to trust the staff at the hotel and form genuine friendships, becoming friends with Niffty, although he was afraid of Niffty's sadistic behaviors.
In "Dad Beat Dad", as a group of loan sharks attack the hotel to get Mimzy, Sir Pentious bravely saves Niffty from being crushed by the hotel's rubble.
In "Welcome to Heaven", Sir Pentious protects Niffty in the bar and explains to her that the entire floor is dirty because it is a public place. Following his supposed death, Niffty was among those that honor his sacrifice at his memorial after the hotel's reconstruction.
Husk
- "Hey, at least you can take a beating like a champ. You did okay, new kid."
- ―Husk, to Sir Pentious.
Sir Pentious earns Husk's respect
Sir Pentious considered Husk an enemy during his attacks on the hotel. After settling down and seeking redemption, Sir Pentious showed distrust of his other roommates, including Husk, so Vaggie led a trust exercise to get everyone involved in a turf battle. After the battle, Sir Pentious earned Husk's respect when he managed to stay on his feet during a battle against a demon and the two began to become friends.
However, Husk recognized Sir Pentious' personality, seeing him as an "insecure buffoon" who spies on everyone while they sleep. Despite the prejudices, Sir Pentious formed a close friendship with Husk, who considered him a good drinking buddy with Angel Dust and Niffty. After his sacrifice and supposed death at the hands of Adam, Husk was among those that honor his sacrifice at his memorial after the hotel's reconstruction.
Overlords
Alastor
- "We've done battle, like... 20 times."
- ―Sir Pentious, to Alastor
Sir Pentious learns to apologize to Alastor
Alastor and Sir Pentious apparently knew each other before the events of the pilot and are enemies, at least from Sir Pentious's perspective; Alastor doesn't seem to recognize him or take him seriously, as he answers "Do I know you?" after Sir Pentious threatened Alastor. It is revealed in "Radio Killed the Video Star", that Alastor has defeated him roughly 20 times previously. After his recent defeat, Sir Pentious headed to the hotel to "redeem himself", and in his first lesson he apologized to Alastor for damaging his outfit, despite Alastor subsequently mocking him by burning the cloth he returned for the Overlord's coat.
The Vees
Sir Pentious idolized the Vees. However, he would later be abandoned by the Vees' leader, Vox, after he failed his spaying mission at the Hazbin Hotel.
Vox
- " I can't believe we thought you could handle even something this simple! Do us a favor, if they don't kill you, go ahead and do it yourself! You MISERABLE FAILURE!"
- ―Vox, to Sir Pentious
At some point in "Radio Killed the Video Star", Vox found and recruited Sir Pentious to be a spy at the Hazbin Hotel to prevent any deal between Alastor and Charlie. After Sir Pentious called Vox on his watch after being caught, Vox laughs, saying it hasn't been a day. Sir Pentious begs for Vox to get him out, but Vox scolds him and tells him to kill himself if the hotel staff doesn't, and ends the call after calling him a "miserable failure".
Love Interests
Cherri Bomb
- "Miss Cherri Bomb, I love you. Remember me!"
- ―General Pentious, to Cherri.
Sir Pentious facing Cherri
Cherri Bomb is Sir Pentious' former archnemesis and love interest. Cherri can be seen engaging in battle with him in one of the turf wars over new territory. She appears to not take him seriously and mocks him during the battle.
In "Welcome to Heaven", Sir Pentious appears to have a crush on her as he tries to impress her and attempts to buy her drinks and is also at some points shown blushing at her. He also asks her if she wanted to "do a sex" with him. When he was able to get rid of the demons who wanted to have sex with him, Sir Pentious asked Angel and Husk about Cherri, cursing when he found out that she was having relations with another demon.
General Pentious kisses Cherri
In "The Show Must Go On", General Pentious praises Cherri for being a worthy opponent, who appears fascinated by his compliments, but before he could confess, he asks her not to die in battle and runs away. During the battle against the Exorcists, Sir Pentious reveals his true feelings to her and they share a kiss. Cherri is devastated when she sees Sir Pentious' apparent death and honors him with her other friends after the battle.
Friends
Angel Dust
- "Thank you for pulling me out of there."
- ―Sir Pentious, to Angel Dust
Sir Pentious is disgusted by Angel's sexual comments
Angel Dust is the former fellow hotel client and good friend of Sir Pentious. Initially, Angel helps Cherri Bomb fight Sir Pentious in the turf war, in which he constantly mocks him with various sex jokes. Sir Pentious mistakes him for his son after misunderstanding Angel's attempt to call him "Daddy". Sir Pentious sought revenge against Angel at the Happy Hotel before being defeated by Alastor.
Angel continues to mock and distrust Sir Pentious as he attempts to redeem himself at the hotel, feeling bad about Charlie's appreciation of Pentious, before discovering his alliance with Vox. In response to Angel's insults, Sir Pentious treats him with hostility, calling him a "whore."
Sir Pentious makes amends with Angel
After agreeing to fully redeem himself, Sir Pentious agreed to live in the hotel, participating in a trust exercise, in which he begins to befriend Angel after surviving a turf battle. Despite their friendship, Sir Pentious gets into an argument over Angel's sex advances. Sir Pentious was cheerful when he spent time with Angel, Husk, Niffty and Cherri at the bar, faithfully acknowledging them as his friends.
In "The Show Must Go On", to help Sir Pentious win over Cherri, Angel tells his friend that Sir Pentious has two dicks. Angel was devastated after seeing Pentious' apparent death, recognizing his friend's efforts and honoring his sacrifice after the battle.
The Royal Family
Lucifer Morningstar
- "Your majesty!"
- ―Sir Pentious, to Lucifer Morningstar
Sir Pentious gazes with admiration at Lucifer
In "Dad Beat Dad", Sir Pentious meets Charlie's father, Lucifer, for the first time. Although they haven't interacted that much nor directly, Sir Pentious did aggressively salute Lucifer and call him "your majesty" before falling over onto the table. This indicates some respect that Sir Pentious has for the king and even some admiration. During the hotel's reconstruction, Lucifer paid respects to Sir Pentious' sacrifice.
Enemies
Adam
General Pentious being blasted by Adam
In defense of the hotel, Pentious, as General Pentious, helped his friends combat Adam's army of Exorcists, who sought to kill everyone in the hotel. Because Charlie and Vaggie were running out of options, Sir Pentious decided to sacrifice himself and took his airship to try to kill him with his death ray, however, Adam easily evaporated him in front of his friends.
Heaven
Emily and Sera
The two angels reactions
After Sir Pentious ascended to Heaven in front of the two angels as one himself, he greeting them with a simple "hello". While the two have yet to respond, with Sir Pentious' arrival, the two seraphim were shocked, but Sera became visibly horrified while Emily became happily excited.