|Pairing:||Stiles Stilinski/Jackson Whittemore|
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Stiles Stilinski/Jackson Whittemore or Stackson is the relationship between Stiles Stilinski and Jackson Whittemore on the television show Teen Wolf. This ship is considered a rare pair because it doesn't come up too often in fan fictions or fan art.
Stackson Week is run on Tumblr, the latest one being in 2019.
Jackson and Stiles are long time rivals. Jackson is the popular, rich kid at school who doesn't bother with anyone he sees as below him. On the surface, at the very beginning of the show, Jackson has everything that Stiles wants: first line on the lacrosse team, Lydia Martin as a girlfriend, and enough money and popularity to do basically whatever he wants. After Stiles's best friend, Scott McCall is bitten, Jackson's animosity toward Scott, and subsequently Stiles, leads to butting heads.
During Night School, 01x07, Stiles ends up punching Jackson after Jackson attempts to coerce Stiles into calling the Sheriff for help. After punching Jackson, however, Stiles does call his dad (but gets taken directly to voicemail), to the bemusement of Jackson.
In Co-Captain, 01x10, Scott and Stiles drive into an empty parking lot where Chris intercepted Jackson. Stiles gets Jackson's attention by saying, "You want a ride? Hey, come on, Jackson. You're way too pretty to be out here all by yourself."
In Code-Breaker, 01x12, after Jackson takes Lydia to the hospital after Peter's assault and Peter lets Stiles go, Stiles meets up with Jackson at the hospital. They both decide to go confront Peter, but Stiles doesn't have a car. Jackson offers up his Porsche out of guilt. Stiles agrees on the condition that he gets to drive, snatching the keys away from Jackson. Immediately upon deciding this, Chris confronts them both, and when Chris asks them about whether they've seen Scott, Stiles easily lies while Jackson is a deer in headlights. Stiles is annoyed with Jackson's inability to lie under pressure. Later, when they're finally driving to the Hale house, Jackson gripes about his Porsche not being an "all terrain vehicle" to which Stiles snipes back "Yeah. Did you pay for it?" Jackson says No, and Stiles tells him to Shut up.
In Omega, 02x01, Lydia goes missing from the hospital, and Scott and Stiles go to Jackson about helping her. Jackson is flippant about Lydia potentially turning into a werewolf, saying, "Well, I think that if Lydia's turning, she's not the one that's gonna need help." Scott asks for what he means, and he adds, "Oh, God, you've got it all backwards, McCall. When I was with Lydia, you should have seen the scratch marks she left on me. What do you think she's gonna do with a set of real claws? Heh." Jackson leaves, and Stiles ends up agreeing with him, saying, "All right, it's causing me severe mental anguish to say this, but he's right."
In Frenemy, 02x06, Jackson's kidnapped into a prison van after attacking the Jungle as the kanima. When he wakes up and realizes this, he shouts, "Stiles! McCall! I'm gonna kill you!" (contrary to popular belief, Jackson never calls Stiles "Stilinski" once in the show ). Stiles brings Jackson a sandwich and complains about having to put pants on Jackson's naked body, professing, "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. "
In Masterplan, 02x12, after it's perceived that Jackson has died, Stiles is the first to take a step toward Jackson's body before Jackson starts twitching. After Jackson gets up and hugs Lydia, Jackson's gaze can be interpreted as looking in the direction of Scott and Stiles. Stiles, who who's been crying, dismisses the tears as being about his Jeep getting scratched as he, again, walks toward Jackson and Lydia.
At the beginning of season 3, the audience finds out the Jackson's parents sent him to live in London.
In season 6B, Jackson briefly returns with Ethan, who became his boyfriend at some point after Ethan and Danny broke up at the end of season 3B. Jackson has a run-in with Stiles and Lydia where Stiles is more confused by the revelation that Jackson is dating Ethan than the fact that Jackson is openly bisexual now.
Stackson is statistically considered a rare pair, however, it's the fifth most popular Stiles ship on AO3, behind the likes of Sterek, Steter, Sciles, and Stydia.
People ship Stiles and Jackson with a passion. Some fans like the hateful relationship that Stiles and Jackson have in canon. Other people are attracted to the potential of Stiles and Jackson's relationship if Jackson had stayed during season 3, especially with the aftermath of the nogitsune.Fanfictionfridge on Tumblr explains:
The seeds of similarity between Stiles and Jackson are that they’re both shaped by loss. Loss of family/friends, loss of innocence, loss of self-image. They also severely blame themselves for everything bad in their lives. And I think they’d find solace in one another. Because while they put up a front with everyone else in their lives about being “fine” and “better,” they don’t need to hold back when they interact with each other. They can be as blunt and harsh as they need to be without caring what the other thinks. The fun part is when they eventually realize they do care, and they start licking the other’s wounds. 
Common Tropes in Fanworks
- Enemies to lovers / Rivals to lovers - with them being antagonistic towards each other before whoops feelings
- Idiots to lovers - where they're oblivious to their own developing feelings
- Pigtail pulling - teasing that is actually a cover for feels, could be Stiles or Jackson doing it, though usually depicted as Jackson
- A/B/O - Jackson wants to be an alpha male so desperately (plus he's actually an Omega in canon for different reasons) that it's the perfect recipes for omega!Jackson
- Hurt/Comfort - an exploration of post-kanima and post-nogitsune pain
- Friends with benefits - the two of them finding common ground in sex
- Dirty Dirty, Filthy Filthy by Mandibles
- get you on your knees by addandsubtract
- Hallway Hookups by Onlymystory
- Happy Endings are for Winners by whatthefridge
- I'll Dissolve When The Rain Pours In, When The Nightmares Take Me by clotpolesonly
- It Fills My Head Up and Gets Louder by addandsubtract
- It Gets Under My Skin (Take in the Extent of My Sin) by taylorpotato (must be logged into AO3 to view)
- Let Me Keep You Safe (Just Let Me Keep You) by tryslora (must be logged into AO3 to view)
- The Doghouse Screw by ahab2692
- When the Dumb Collide by whatthefridge
- When We Were Monsters by whatthefridge
- You Complete(ly Irritate) Me by rospeaks
- I Love You The Same
- I Can't Give It Up
- Dancing With The Devil
- Inside You
- Lonely Souls
- Eyes On Fire
- Lineart looks by elioperlman
- Procrastination doodle by tea-demon
- Kissy face by jinjidraws
- Comic: We weren’t friends, and will never be by ilysano
- Kissing in color palette challenge by fanfictionfridge
- Mermaids (headshots) by fanfictionfridge
- Mermaids (full-body) by fanfictionfridge
- Hugging portrait by fanfictionfridge
- Collection of Stackson photomanips by whatthefridge
- Beacon Creature Show, Archived version
Other Fan Works
Manip gif by whatthefridge
Archives and Communities
- Stackson Week on Tumblr
- New Stackson Discord
- Stiles Shipping Central
- Stiles Stilinski/Jackson Whittemore tag on AO3
- Stackson tag on Tumblr
- Rare Pair Exchange's Stackson Page
- AO3 Stackson Feed
- From fanfictionfridge's meta: Jackson, and the myth he refers to Scott and Stiles exclusively by surname
- Summary of Stiles-ship fics on AO3 (as of Feb 23, 2020)
- From fanfictionfridge's Tumblr ask response