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Dermott first appeared in the Venture Family's life when he attended Rusty's Day Camp for Boy Adventurers. During the camp, Dermott makes a nuisance of himself by bragging about his supposed martial arts skills and mocking just about everything being presented. Dean Venture fears him on first sight, having never seen another teenager, and especially one that size, before. Hank, however, becomes fast friends with Dermott, attempting to make jokes with him. His constant heckling of Brock Samson actually leads Brock to looking for excuses or ways to fight him fairly. After insulting Triana Orpheus, Dean's crush, Dean attacks and pummels Dermott.
When his mother Margaret picks him up from the camp she asks him if he met a man that she told him is his father. Dermott was under the impression that Brock Samson is his father after a one night stand he had with Margaret. When he is caught by Henchman #24 during an attack on the Venture Compound, Dermott tells #24 that he might be Brock's "long lost son".
His friendship with Hank grows stronger as they hang out more, with Dermott influencing the way Hank acts and speaks, with Hank becoming more and more rebellious. Hank and Dermott start a band together, Shallow Gravy, with Hank on bass and Dermott handling vocals, and HELPeR acting as a drum machine. After much negotiation, they're allowed a few minutes to perform at the Venture's homeschool prom. They perform Jacket, the only song they've completed. The band is later profiled in the documentary From the Ladle to the Grave: The Shallow Gravy Story with The Monarch taking credit for breaking the band up by destroying HELPeR.
Though Dermott believes that Margaret is his mother and Nikki is his sister, in truth his mother is Nikki, who got pregnant at 15. Margaret decided they would raise Dermott as Margaret's son to avoid any scandal and embarrassment that a pregnant teen girl would bring, as well as allow Nikki to mature with Margaret taking the bulk of the responsibility.
Margaret leads him to believe that Brock is his father, causing Dermott to both revere and purposely annoy him. His father is actually Rusty Venture, who slept with Nikki while under the impression she was 20-years-old. When he found out he'd gotten Nikki pregnant, Margaret blackmails him into supporting the child with unofficial payments rather than have him arrested for statutory rape.
In "Everybody comes to Hank's" things become more complicated when Nikki sleeps with Hank. Hank accidentally finds out the truth of Dermott's parentage through a magic charm spell. He is horrified and disgusted that his friend is also his half-brother but his memories, however, are erased by Brock and Shore Leave who are some of the few to know Dermott's heritage.
In "Momma's Boy" Dr. Orpheus realized that Dermott is a Venture when he responds to his mental cry for help. When he informs Dermott of the fact, it is readily accepted and at the end of the episode he calls Dr. venture "dad" shocking Thaddeus, Hank, and Dean.