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This is entirely based off of the Hook Family headcanon/theory that I posted back in August (I’d recommend reading that first!).

It’s been eight months since I made that post and for some reason I’m now thinking about it obsessively in the middle of the night, so I wrote up this timeline of the events described in said post just to clear some things up (mostly for myself lol). It’s just for fun, so please don’t take it seriously if you don’t want to!

Please note that for the sake of this headcanon, time passes about 56% more slowly in Wonderland (I may be wrong, I suck at math) and I’m also basing this entire thing off of the assumption that Red and Chloe went back 35 years to 1986, the Isle was created in 1996 and that the main VKs were born in the year 2000-2001 (credits to @samanthaswishes for her breakdown of the characters’ ages)

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July 1985: Princess Bridget is enrolled in Merlin Academy and leaves Wonderland for the first time. She meets James Hook and they form an unlikely friendship (and soon-to-be toxic relationship).

October 1986: Red and Chloe go back in time to this point. Castlecoming takes place a few weeks later towards the end of the month and Princess Bridget is publicly humiliated by the villain kids at the event.

May 1987: Most of the villain/hero characters (the Descendants characters’ parents) graduate from school. The younger ones graduate in ‘88 and ‘89

1988 - 1995: Complete chaos. Most of the well-known fairytales take place during these eight years. Princess Bridget has her coronation and becomes the Queen of Hearts in Wonderland.

April-June 1995: Prince Adam marries Belle and they become King and Queen. Adam’s first order as king is to unite all of the kingdoms under the flag of Auradon. His second order is to revisit old plans for the Isle of the Lost and begin carrying out said plans. Queen Bridget attends Adam’s council meetings but ultimately decides not to have her kingdom join Auradon.

July 1995: Captain James Hook runs away to Wonderland upon hearing the first rumors of the Isle’s creation. Queen Bridget makes him the executive officer of her armies and marries him against her parents’ wishes (and against Wonderland’s former laws, too).

December 1995: The Isle of the Lost is officially completed and the magical dome is created. King Adam begins rounding up the villains and their families and imprisoning them on the Isle (sweet guy).

January 1996: The last of the villains are captured and imprisoned on the Isle (except James, who is avoiding punishment because Auradon can’t control a thing that goes on inside Wonderland).

February 1996: Discussions begin in Wonderland about giving James the title of “King of Hearts,” to which James responds that they “put a dart in that subject”.

March 1996: James begins having piracy withdrawals (lol). He begins leaving Wonderland for days and weeks at a time to visit with his friends and crew on the Isle (possibly to prove that he hadn’t completely abandoned them or lost his personal freedom, or both), and King Adam has no choice but to allow him to do so out of fear of being attacked by Wonderland’s army. Bridget grows jealous of James’ visits.

April 1996: Princess Red and Princess Harriet are born to the Queen of Hearts and Captain Hook.

September 1996-April 1998: Even more chaos. Many events take place during these 20 months that lead to the severance of any remaining truces or treaties between Auradon and Wonderland (I’m still figuring this whole part out). Captain Hook tries to smuggle his crew off the Isle and fails. Ursula’s younger sister, Uliana, is killed due to unknown causes. Several Auradon soldiers go missing and several more go completely mad. Many Wonderland soldiers go missing as well. Auradon and Wonderland are on the brink of war and tensions are at an all-time high. The Queen of Hearts earns a reputation as a terrifying, unreasonable ruler even though Captain Hook has secretly been the one pulling the strings. They have lots of fights that steadily get worse over time.

May 1998: King Adam announces that the portal between Wonderland and Auradon will be closed towards the end of the year.

June 1998: Following a particularly bad argument, Queen of Hearts strips Captain Hook of his title as Executive Officer and restricts him from leaving the castle grounds.

October 1998: Harriet Hook’s birthday according to the Isle residents.

January 1999: Captain Hook leaves Wonderland and takes his daughter, Harriet, with him. The portal between Wonderland and Auradon is sealed that same day. James and Harriet are brought to the Isle of the Lost. The Queen of Hearts is left heartbroken and devastated.

October 1999: Captain Hook meets Sarah Sanderson on the Isle.

November 2000: Harry Hook is born to Captain Hook and Sarah Sanderson.

July 2003: CJ Hook is born to Captain Hook and Sarah Sanderson.

September 2017: The events of Descendants 1 take place.

March 2018: The events of Descendants 2 take place.

July 2019: The events of Descendants 3 take place. The magical barrier surrounding the Isle of the Lost is officially brought down.

September 2021: Red (25 but actually 16 in Wonderland and biologically) begins attending to Auradon Prep, thus triggering the events of “Rise of Red”.

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Fun fact: I wrote the first draft for this timeline on a white board at 1:45am in my bed. I don’t know why, I just felt like it was necessary to mention this.

Also in case you haven’t noticed by now, this entire post has been a fanfic in disguise (which I will probably never write into a real story because I am lazy asf). Anyway, I thank you very much for your time! :)

Even in the Hookedheart universe. Hook still loses his wife by being sent to the Isle and has to raise their three kids alone.--who are again each under ten. But this time with the added trauma/heartbreak of knowing that he has a fourth kid out there that he will likely never know...

He just cannot seem to have a normal life with both his wife and kids.

Hook needs one of these hugs:

Hook is/was the same.

I go back and forth on if Red would even use the watch or not in the scenario where Cinderella tells Bridget and her that she's the one who snitched to Beast, (maybe that's just because of all the stuff with Harry, Uma, and Hook we've added with this scenario, though) and when I do think of her using the watch it's almost always after Cinderella's execution.

Things would probably go best if it was a mash-up of canon RoR and the snitch reveal. Red sentences Cinderella to death (she's not sorry), Chloe tries to fight back against that, but unlike in canon instead of Red purposely using the watch, she uses it by accident when she and Chloe are fighting. I don't know if that's even possible or not, but let's pretend it is.

I keep replaying that scene where young Hook basically flirts with Chloe and Chloe all but challenges him to a fight, over in my head and thinking about what Red's reaction would be. Because Red's probably SO confused, thinking, "What is he doing with the people bullying my mom? Didn't mom say that they were together in high school??"

But Red's also not going to let Chloe mess with Hook too much. Chloe, someone she's just met and doesn't fully trust, and the daughter of the woman who (she thinks) killed her family, including the future version of the admittedly irritating guy in front of her. Nobody is messing with Red's dad, but Red.

I just think this is an interesting idea. I'd love to hear your thoughts, but no pressure!

I LOVE this, actually!!! And hey who says using the pocket watch by accident isn't possible? Especially when you're being shoved around in a fight?

It could be like when Red eyes Charming in canon and Chloe's like 'that's my dad'

Only it would be Red saying "hey watch it! That's my dad!"

But yeah Red's definitely going to have a few words for Hook about the fact that he 'hangs around' with the people who bullied her mother! Like "Just answer me one question....HOW DO YOU GO FROM ENJOYING HER PAIN TO HAVING FOUR KIDS?!"

One thing I would find interesting is that if Red stopped the prank here, how do Hook and Bridget get together? As it was the prank that started them off. Actually why do I see Hook wanting to recruit Red? And trying to offer her a place in the pack? I mean Red would fit in well. And Red would accept as she sees it as a way to protect Bridget and nudge Hook towards her? Wait...if Red knows that cinderella basically betrays her mother, why do I see her being determined to 'split' ella and Bridget up.

Like her telling Bridget, "Your 'best friend' got your KIDS sent to PRISON! As TODDLERS! All because she didn't like their father!"

Or imagine Red and Chloe fighting about again with Chloe insisting that her mother wouldn't do that, not to kids! And Red screaming that she did! And in doing so she ruined both Bridget's and Red's lives! Red ends up crying with younger Bridget. Which causes a whole mix of emotions because this is the first time her mother's hugged her in...she can't even remember. And part of her is screaming at herself to stop, because she can't cry in front of her mother! But younger Bridget's just soothing her and letting her cry, which just makes Red cry harder...

But yeah just something about a scenario where Red knows that Hook is her father and knows what cinderella did when going back in time appeals to me very much!

Like instead of the prank...it's their future daughter setting them up, lol

I'm gonna say that Bridget still has her "Fine make me your villain." Moment for Auradon making her family and her live in a prison but also as a way to protect her kids. Hook can't always be with them to protect them, and she can't keep them safe if people think that she can be pushed around. To do that, she makes herself just as feared as her husband is. So Bridget and Hook become the power couple of the Isle.

Bridget and Hook are still terrifying to the rest of the Isle, but since they still have their whole family together, they'd be closer to a DSoR dynamic with their kids. They're more toughened versions of themselves than they were in Wonderland, like we said with Hook, but still good parents who love their kids and, of course, if someone messes with their family, it's off with their heads or walking the plank.

The Hooklings all have a happier childhood than in canon, having both parents, safer of not debatable but definitely happier for everyone involved. I can see Red as a mix of her canon rebel self but also DSoR, where she's the baby of the family that has two overprotective parents and three overprotective siblings.

The older kids I feel would act about the same. Overall, the differences would be Harriet having less stress over having to watch and protect her younger siblings when her dad isn't around. She still does those things, of course. It's who she is, but she doesn't need to worry about them as much with her mom being there.

Harry and CJ are the closest to canon. Harry is still a lot like Hook, but he gets to continue being a mama's boy like he was in Wonderland. CJ is still a walking ball of chaos and a hellraiser, but she gets to be a big sister and do those things with Red, and she gets to know her mom.

I can picture Bridget having a bakery in or as close as possible to pirate territory. It's one of the best places to eat on the Isle because she can somehow make the rotten scraps that Auradon leaves taste good, and some of the adults who had similar things before the Isle can hardly tell the difference.

The Hooklings take turns between working at Hook's shop and the bakery. When they were little, Hook would bring CJ and Red to his shop because it's closer to the Jolly Roger (where they all live) and the younger girls liked to stab the customers with fish hooks and throw bait at them.

Harriet and Harry would go with Bridget to the bakery because Harriet was old enough to be away from the ship for long periods, and she liked helping Bridget bake. Harry went because he liked following Bridget around (mama's boy), and he liked throwing flour at Harriet and taste testing.

Bridget is constantly telling the Merlin VKs that they should come by while wearing a threatening smile. They do not. They're not that stupid. This goes on for sixteen years straight. She's not actually going to poison them to death. Hook would be upset. And if something happened to Uliana, that would upset Uma, which would upset Harry, which would upset Bridget

Uliana is constantly smacking cookies and cupcakes out of Uriah's, Marissa's, and Uma's hands. They know they're not allowed to eat anything from the bakery, but their friends are always eating them, so why can't they? Bridget's not going to poison the kids. She's not that evil. And again, that would upset her kids.

Bridget raged when the Core Four were chosen to go to Auradon in D1, and none of her four kids were. Come D2, she's incredibly proud that Harry and the Lost Revenge crew kidnapped the King of Auradon.

As you can see, I have so many thoughts on this. This is what I got for now.

THIS! Oh I love this! It's like the perfect combination of them being hardened but still being loving parents!

I'm not too sure how exactly they would have a bakery on the isle with no real access to things like flour. But I love the idea! So maybe it's flourless treats! And with them running both a fish shop and a bakery, two food sources. They really would be at the top of the 'food chain'. Probably just under Hades. The adult villains who have brains would be tripping over themselves to make alliances.

Though, imagine Red being born and Bridget just looks at Hook and says "She's our last child." There is no way she's going to bring another child into a place with no medical system And all the kids would have...well as happier childhood as they can growing up in a prison when innocent.

Little Harry following Bridget around is adorable, he would guard her with his life and make his daddy proud! :D And CJ actaully knowing her mom my heart! Yes!

And yeah I can see Bridget screaming her head off the day she finds out the Core Four got picked. Like after everything Maleficent's done to the others of the Isle taking what little good food they do get and leaving the rest to suffer...it's still her child that gets picked?! It would enrage her.

WHY is the descendants universe giving Hook so many kids?!

He was never the type that you would think would have a heap of kids. If you're a hookedheart shipper he's now up to 5 kids!

That just seems really out of character for Hook.

Yeah we get it writers a pirate has to have a crew, but that doesn't mean it has to be a self made crew!

If you want to have a character that you can give a heap of kids to bring GASTON in!