In his original season, Flynn obtained the reputation of being a major physical threat, which made him generally disliked by his fellow competitors. He is remembered for
Flynn is the first person to greet the host upon entering in "Being Bitter Isn't Fun". The host ignores him, however, and continues to professionally explain the location while the contestants file in. Hearing "Te Urewera," Flynn asks what "a Te Urewera is," saying it sounds like a brand of tuna, showing everyone his childish nature. The host concludes his speech, and announces that the first challenge will take place momentarily. Flynn, thinking back to previous seasons, worridely asks about contestant introductions. Wording his question wrong, Denny Hallman thinks Flynn had been in the previous season, and goes on to suggest that he is good at the game and handsome.
Flynn reveals his dedication to Finale during the challenge, when the contestants are shown a grid, which displays past contestants of the series. Flynn is please by this, calling himself a "real Finale fanboy," and remarking that he's seen every season. He continues his positivitey through a portion of the challenge, making random comments including "This game is gonna be so much fun!" and "I'm so EXCITED." Sooner into the challenge, however, Flynn is discouraged, announcing to everyone that he doesn't know all of the answers, and may not be a fan like he thought he was.
Controversy strikes when the host gives Catwoman a point for submitting the answer "EV," as an abbreviation for the contestant Evil Valentine. Flynn gets upset, complaining that he doesn't know who "EV" is. Once it is clarified, Flynn argues that no one uses the abbreviation for Evil Valentine, but instead call her "Evil Loud Mouth Woman." He then begins to subconciously get off topic, saying Evil Valentine is mean, just like his father.
Despite having doubts, Flynn ends up winning the challenge, but can't decide who to Reward, claiming that everyone is "totally awesome." He decides to let random.org choose for him. Thurstee comments that Flynn should Reward him due to the fact that he is, according to himself, helping Flynn win. Flynn returns with the results, saying that Random.org chose Catwoman. Therefore, he Rewards her. Unlike the previous decision, Flynn chooses to Punish Maleficent quickly, who he says tried to hurt him. Maleficent recieves a dud, to which Flynn says sounds unhealthy.
With the Reward and Punishment distributed, the host informs the contestants that they will be staying in tee-pees for the season. Hearing "pee," Flynn frowns and questions if the season will be based around urine. Just then, the host tosses him the map to the tee-pees. Instead of leading his fellow competitors to their home, Flynn tells everyone that he doesn't like sleeping alone, and asks if he can stay with someone tonight, because he's scared of "bears and stuff." Surprisingly, both Catwoman and Princess Gingerbread both offer to stay with Flynn for the night. Flynn responds to Princess Gingerbread happily, and asks her if she has a teddy bear, as he misses his teddy bear Snugglebuggle back home.
While the contestants are voting, Flynn informs everyone that he got a text from his mom, who said to tell everyone she said "hi." Suddenly, Flynn's mother's airplane flies over Te Urewera and air drops cookies. This is fortunate for the host, who serves the cookies for dinner. Denny, who had previously called Flynn handsome, asks him if he can kiss him after the two recieve cookies. Flynn doesn't answer, but Denny kisses him anyway. Despite voting Chelsea, Flynn seems confused when Madea is given cookies, due to the #VoteMadeaOff2014 alliance existing. After the contestants are sent back to the tee-pees, Flynn announces that he is throwing a party in his hut. Only Catwoman and Hunter Gatherer seem interested.
Flynn wins his second immunity in "THERE'S NO CRYING IN SURVIVAL", along with Catwoman, who is he paired with in the Performance Challenge. When the contestants arrive for the challenge that morning, Flynn randomly reannounces that he had thrown a party the previous night, and assures everyone that the drinks were non-alcoholic. Hunter comments disappointedly that there was no piss, but Flynn assures him that he put some piss in his apple cider.
After the challenge is explained, Flynn seems nervous about finding a partner, and asks who wants to be his partner. Hunter and Catwoman both offer, and Flynn turns down Hunter because Catwoman had asked first. Hunter seems insulted, so Flynn asks Catwoman if she would care if he switched to Hunter. In response, Catwoman extends her claws and confirms that Flynn is her partner. Moments later, when HeartAndSoul suddenly speaks, Flynn remarks that he forgot HeartAndSoul was in the game and says he can't remember the names of the other contestants.
Flynn and Catwoman are the second group to perform in the challenge. Flynn plays Evil Valentine from Oaxaca while Catwoman plays Katy Perry from Broadway. The scene begins with Flynn storming in and announcing that he is Evil Valentine. Catwoman, as Katy Perry, stands from her "throne," and causing Flynn to ask who she is, and call her a peasant. Catwoman is offended by this, and asks Flynn if he wants to "play with magic," referring to one of Katy's quotes from her original season. The two being to argue, Flynn threatening to vaporize Katy Perry, while Catwoman telling Evil Valentine she'll turn her to dust. The scene concludes with Flynn winning the "fight," vaporizing Catwoman, the stage, then the audience in the process, causing him to recieve snarky remarks from Denny and Maleficent. At the last minute, Catwoman turns Flynn to dust, and the scene is over. Only Gingerbread Princess claps.
Flynn doesn't speak again until the next-to-last performance by HeartAndSoul and Gingerbread Princess, when he seems discontent that HeartAndSoul is also playing Evil Valentine. Flynn goes on to critisize the performance, remarking that HeartAndSoul is just repeating the same thing over and over, but gives them a 7/10 for effort. Sooner into the performance, Flynn begins to get upset, and frowns and begins to repeat "stop." Flynn grows even more upset during the final performance, when it is revealed that Madea is also playing Evil Valentine. Sometime during the performance, Flynn faints.
After the challenge, Flynn wakes up, realizes he had fainted, and says he misses his mommy. After Madea is told that her performance with Maleficent did not win immunity, she tells Flynn to die, and he says he remembers he fainted because of their performance. Flynn tells Madea that his mommy would not approve of her telling him to die. Despite their performance getting mostly negative reception, Flynn and Catwoman win the challenge, and are immune. Flynn gets excited, claims he is surprised, and faints. He wakes up only moments later, with Maleficent raises her hands in preparation to curse him.
The host tells Catwoman and Flynn to make their Reward and Punishment, and Flynn happily tells Catwoman she can Reward someone, while he does the Punishment, even though he doesn't like to. Catwoman, however, wants to Punish someone, so Flynn reluctantly agrees to let her Punish someone with him, but suddenly changes his mind again, and lets Catwoman do both. While Catwoman is making her choices, Jamez Emo sarcastically asks Flynn if he is stupid, which upsets him. Flynn changes his mind yet again, and asks Princess Gingerbread to draw a name out of a hat to decide the Punishment. She approves of this idea, so Flynn draws a name, which turns out to be Madea.
At the elimination, (which begins promptly after Madea quits the game), Flynn asks Princess Gingerbread if he can hug her. He responds negatively when it is announced the dinner will be Madea's bottled sweat. While the contestants are sending in votes, Flynn shows everyone the book of puns that he found. No one seems to care, so Flynn clears his throat and says one of his jokes. Only Denny responds, saying that the joke was really funny. Flynn enjoys telling more jokes, but soon acidentally drops his book in a fire. He begins to cry, and Denny trys to comfort him. It is soon revealed that Flynn is safe from elimination, but he does not want his glass of Madea sweat, so he passes it to Hunter. Flynn is happy to recieve a hug from Princess Gingerbread, who is also safe. Jamez is eliminated, and angrily warns Flynn that the show is "rigged for females," and that he is going to be "pussy-whipped." Flynn mostly ignores the warning, only complaining that "pussy" is a bad word.
Flynn continues his winning streak in "Some King Of Anxiety Thing," after winning the Location Trivia challenge. Immediately upon entering the challenge, Flynn asks the host when the jury starts. The host tells him it starts at the final 7. Flynn dominates the challenge and quickly wins, which earns him a hug from Princess Gingerbread. Flynn is asked to Reward and Punish, and as usual, he is reluctant to make a decision. Fortunately, the choice is held off when Denny seeks medical attention. Flynn asks Denny if Rewarding him will make him feel better, but Denny assures him that that is not the issue.