Jared Padalecki and Jensen Ackles have spent years trying to leave the Winchester brothers behind. Their characters, Sam and Dean, wrapped up their story in 2020 after 15 seasons of Supernatural. But some habits do not die. During a recent Creation Entertainment convention segment, the two actors sat down for a lighthearted game of “Guess the Number.” Before the game could begin, Padalecki suggested a quick round of rock, paper, scissors to decide who would ask the first question. Ackles threw scissors. Padalecki threw rock, won the round, and delivered a line that has followed Dean Winchester for nearly two decades: “Always with the scissors.” The moment was shared by Creation Entertainment on November 3, 2026, and the clip has since circulated among Supernatural fans who recognised the callback immediately. The scissors joke is not just a random quip. It ties back to a specific Season 2 episode, a running character trait, and a sibling dynamic that defined one of The CW’s longest-running shows.
The ‘Guess the Number’ Game That Turned Into a Supernatural Throwback
The segment was part of the Road So Far… The Road Ahead Tour, a series of live Supernatural conventions organised by Creation Entertainment. The Orlando stop took place September 11–13, 2026, at the DoubleTree by Hilton Orlando Hotel, with Ackles, Padalecki, and Misha Collins headlining the weekend. Creation Entertainment revived the “Guess the Number” forehead game after a previous version featuring Padalecki and Collins went viral on social media.
For the Jared and Jensen version, Padalecki had the number 2 on his forehead. Ackles had the number 36. Before the questions started, Padalecki proposed rock, paper, scissors to settle who would go first. Ackles chose scissors without hesitation. Padalecki chose rock and won. The line “Always with the scissors” came out of Padalecki’s mouth almost automatically, and the crowd reacted with the kind of recognition that only comes from a long-running inside joke.
The game itself ended with Ackles guessing his own number, 36, on the first try after asking a clever question about the digits adding up to a multiple of three. But the scissors moment became the part fans kept replaying.
Why Dean Winchester Always Chose Scissors
The joke works because Dean Winchester really did always choose scissors. Supernatural used rock, paper, scissors as a quick way for the brothers to settle small decisions, and Dean’s refusal to change his move became a subtle character detail. In the show, Sam noticed the pattern early. Dean would throw scissors, Sam would throw rock, and Sam would win. The repetition was not a writing mistake. It was a quiet way of showing that Dean was predictable in small things, even when he was stubborn about everything else.
The habit first appeared in the Season 2 episode “Heart,” which aired in 2007. The episode follows Sam and Dean as they investigate a werewolf case in San Francisco. Sam develops feelings for a woman named Madison, who may be the werewolf. The brothers need to decide who will stay with Madison and who will go check out a lead. They settle it with rock, paper, scissors. Dean throws scissors. Sam throws rock. Sam wins and says, “Dean, always with the scissors.” Dean protests and demands “two out of three.” They play again. Dean throws scissors again. Sam wins again.
The scene is short, but it does two things. It gives the episode a moment of lightness before the darker werewolf story takes over. It also establishes that Dean’s stubbornness is not always strategic. Sometimes it is just Dean being Dean.
The Episode That Started the ‘Always With the Scissors’ Joke
“Heart” is Supernatural Season 2, Episode 17. The episode is remembered for its tragic ending and for the introduction of Madison, a character who becomes central to Sam’s emotional arc in that season. The rock, paper, scissors scene happens early in the episode, when the brothers are still in investigation mode. The case involves a series of brutal killings that point to a werewolf. Sam and Dean split up to cover more ground, and the game decides who stays with Madison and who follows the lead.
The line “Dean, always with the scissors” became a fan favourite because it captured the brothers’ relationship in a single sentence. Sam is the younger brother who notices patterns. Dean is the older brother who thinks he is unpredictable but is actually very set in his ways. The game also shows that Dean does not mind losing to Sam in small things. He protests, but he plays again. The scissors habit is not about control. It is about comfort.
What the Scissors Habit Says About Sam and Dean
Sam and Dean Winchester are one of the most studied sibling pairs in modern television. Sam is the thoughtful one, the brother who went to Stanford and tried to build a life outside hunting. Dean is the loyal one, the brother who stayed with their father and followed orders. Their dynamic is built on sacrifice, resentment, love, and a shared inability to walk away from each other.
The rock, paper, scissors game fits into that dynamic because it is a harmless way for them to make decisions. They face literal demons, angels, and the apocalypse. But when they need to decide who gets the last piece of pie or who checks the creepy basement, they use a children’s game. Dean’s insistence on scissors makes him the butt of the joke, but it also makes him human. He is not a tactical genius in every moment. He is a guy who likes what he likes and does not see a reason to change.
Sam’s teasing line, “Dean, always with the scissors,” is affectionate. It is the kind of thing a younger brother says when he knows his older brother too well. The fact that Padalecki repeated the line at a 2026 convention shows that the dynamic did not stay on screen. The actors carried it with them.
The Boys Season 5 Reunion: A Different Kind of Winchester Team-Up
The Supernatural reunion did not stop at the convention stage. Jared Padalecki appeared in The Boys Season 5 as Mister Marathon, a speedster Supe and former member of The Seven. Jensen Ackles plays Soldier Boy in the same series. The two actors shared scenes in Episode 5, titled “One Shots,” which was released in April 2026.
The Supernatural reunion in The Boys was not a direct continuation of Sam and Dean. Padalecki’s Mister Marathon is a different character with a different backstory. Mister Marathon was once the world’s fastest man and a member of The Seven before his speed declined. Ackles’ Soldier Boy is a brutal, old-school Supe with a complicated history of his own. The scene brought the two actors back together in a universe created by Eric Kripke, the same showrunner who created Supernatural.
Fans had been waiting for the on-screen reunion since Padalecki’s casting was confirmed. The Boys scene delivered a bloody, chaotic team-up that was very different from the Winchester brothers’ usual dynamic, but it gave longtime viewers another chance to see Padalecki and Ackles share a screen.
Where to Watch the Road So Far Tour Moments
The Road So Far… The Road Ahead Tour continues through 2026 and into 2027. Creation Entertainment has shared convention clips and game segments on its official social media channels, including the “Guess the Number” video featuring Padalecki and Ackles. The full schedule for upcoming stops, including Creation Chicago in November 2026 and Creation Austin in November 2026, is available on the Creation Entertainment website.
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For fans who want to revisit the original scissors moment, Supernatural Season 2, Episode 17, “Heart” is available on streaming platforms where Supernatural is currently licensed. The episode remains a key part of the show’s early seasons and a favourite among fans who grew up with Sam and Dean.
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