|“|| Stiles: "Okay, I brought you some food..."|
Jackson: "Let me out! Now!"
Stiles: "You know, I put those pants on you, all right, buddy? One leg at a time. Being all up-close-and-personal with your junk wasn't exactly a highlight of my day. So, don't think this is fun for me, either. You know, we're actually doing you a favor?"
Jackson: "This is doing me a favor?"
Stiles: "Yes! You're-you're killing people! To death! Yeah. And, until we can figure out how to stop you, you're gonna stay in here. I'm sorry. Now, you want the ham and cheese, or the turkey club?"
Jackson and Stiles were classmates for most of their lives, though they had very few interactions prior to Scott being bitten and turned into a Werewolf. This was most likely due to Stiles' status as an unpopular "benchwarmer" compared to Jackson, who was very popular and the star lacrosse player, not to mention Stiles' obvious long-time romantic interest in Jackson's then-girlfriend Lydia Martin.
Their relationship was largely antagonistic from the very first episode, with taunts and comments thrown around constantly, which ultimately led to Stiles punching Jackson in the face in Night Schooll, though Stiles still reluctantly protected and/or saved Jackson's life on a few occasions. Though the two were at odds due to Jackson bullying Scott into getting him the bite as well, Stiles ultimately enlisted his assistance in backing up Scott, Allison, and Argent in their fight against the Alpha Werewolf Peter Hale at the Hale House ruins.
After finally getting the bite from Derek Hale after he stole Peter's powers, Jackson, instead of becoming a true Werewolf as expected, he became a mutated reptilian shapeshifter known as the Kanima, who can be controlled by others into doing their bidding. Despite their antagonistic relationship, Stiles still did all he could to help Scott and Allison to prevent him from killing anyone while also protecting him from the Hunters who had invaded the town, even going so far as to steal an armored police van in which to lock Jackson up (a move that caused Stiles' father Sheriff Stilinski to briefly be suspended from his job. Afterward, Jackson's lawyer father filed a restraining order against Scott and Stiles, which they ultimately ignored in favor of protecting the school and town from the mysterious person controlling him.
Throughout Season 2, while the Beacon Hills supernaturals and their human allies tried to discover the true identity of the Kanima, Stiles was inadvertently paralyzed by Jackson's Kanima Venom on a number of occasions, though only two of those times were because of direct exposure from the venom in Jackson's claws.
After Jackson left for England at the end of Season 2, they had no interactions until the series finale, The Wolves of War. Stiles, now dating Lydia, showed jealousy when Jackson and Lydia hugged, though again they helped each other and ended the series as allies. Stiles was also shocked to learn that Jackson was now dating Ethan Steiner.
Jackson and Stiles are known as "Stackson" by fans
Throughout Teen Wolf Edit
In Wolf Moon,
In Pack Mentality,
In Magic Bullet,
In The Tell,
In Heart Monitor,
In Night School,
In Wolf's Bane,
In Code Breaker,
In Shape Shifted,
In Ice Pick,
In Party Guessed,
In Master Plan,
- Jackson and Stiles are connected through their history of romantic relationships with Lydia Martin.
- Jackson refers to Scott and Stiles as "Tweedledum and Tweedledumber" as a play on words with the Alice in Wonderland characters Tweedledee and Tweedledum.