Further headcanons/backstory & PLOTTING
Tagging those who are mentioned in this / who this is relevant to, as your stories directly intertwine with mine. If there's a headcanon in here that needs to change because it interferes w/ anything, please let me know!
Rumpelstiltskin Pre-war: Milah and Rumple's marriage was arranged. They'd grown up in the same village, but didn't know each other well. It was a prudent match on both sides, and though they hardly knew each other on their wedding day, they came to love each other. It wasn't a passionate sort of love, more dutiful, but still respectful and they were content in their own way. Milah was scared for Rumple to go to war and she prayed for his safe return.
Post-war: Milah could not reconcile the man that Rumple returned home as to the man who'd left. She initially lashed out at him when he first came in, but then tried her best to accept the fate he'd bestowed upon them, for Baelfire if nothing else. Her respect for him was lost, though, and despite her efforts, by the time Bae was a toddler, she despised Rumple and hated life in the village, where they were taunted and shamed. By the time she yells "Run home, Rumple, it's what you're good at!" the night in the tavern with Killian, it's been six long years since his return and she's too miserable to pretend any more, especially after having been told all sorts of stories by the visiting pirate. She's realized once again the life she could have had. Despite this, she gives Rumple one last chance...and he refuses to move them. That's the final straw, and the ultimate reason she chooses to run away.
Killian Jones
Life at Sea: Milah gets to know Killian while his crew is docked in the village port for a week. She falls in love with him and his tales of adventure, begging him to take her with him and he does. They aren't immediately "pirate and lady" on the ship. Milah insists on paying her way by doing the crew's mending, and she does quite successfully, as she is a very skilled seamstress. She and Killian do start sleeping together fairly soon after she boards, and before long, she spends more time in the Captain's Quarters than her own cabin, and then moves into his quarters entirely. She's not simply "his lady," however, nor does she fuss about life on a ship. She drinks and sings shanties with the crew, and they respect her (and come to accept and love her as only a crew can -- they are effectively her and Killian's family). Killian teaches her everything about being a pirate--from handling a sword to steering the helm, along with participating in cons and raids. By the time she "dies," Milah is effectively co-captain of the ship, minding the ledger and doing more administrative sorts of things, though she can bark orders as well as Killian. She would never call herself "captain," however, or do anything to demean Killian's authority in front of the crew.
Relation to Orion: More details about Orion's birth and her relationship w/ him below this, but I wanted to put something I think is pretty important about the husband/wife/son aspect under Killian's section.
To me, I've always viewed Killian and Milah's love, true love as it is, as also a greedy/selfish sort of love: that is to say, they have a tendency to get wrapped up in each other/lost in the other, and not pay attention to things around them. They don't actively ignore Orion by any means, but I think they can have the tendency to be in their own sort of grown-up world at times...if that makes any sort of sense.
Orion Jones When Milah finds out she's pregnant, she's terrified. She doesn't feel like she deserves to be a mother really, and she's very afraid of messing up, because of the way things turned out with Bae. Throughout her pregnancy, she prays for a girl, because she doesn't think she can emotionally handle another boy. In fact, she and Killian refer to the baby as 'she' and have only picked female names. Then, Orion arrives.
For the first couple of days, Milah goes through a mix of motherly pride and terror. Every memory of Bae as a baby is brought up and she struggles with reconciling the fact that she has a new son, who is not Bae, but a child belonging to her and Killian. They don't actually name him for 2-3 days after he's born, because Milah can't deal with the task.
Killian continually reassures her during this time that it's going to be different, that the baby isn't a replacement, but a second chance, and that they're still going to get Bae back, and he'll have a brother and they'll know each other.
On the second or third day, Milah has Killian take her and the baby above deck for fresh air and to look up at the night sky. Being out in the open, with their child and their ship, with a world of possibility before them calms Milah down and puts things into perspective. It's while she's naming the constellations to the baby that the name Orion (for Orion's Belt) comes to her, and they name him.
Orion is different enough in personality from Bae and after that night, Milah has no trouble seeing him the way Killian described: his own person. She is a loving mother, teaching him what she can about life at sea, making sure he stays safe, telling him stories about the adventures that she and his father have had.
Baelfire
When her son was small, Milah would take him to the docks at the port with her and point out the big ships passing to and fro. She would tell him stories of far off places and read to him. She would also give him materials to draw and paint with while she worked on her own sketches and paintings, encouraging his creativity.
Leaving Baelfire behind is Milah's biggest regret, one she thinks about constantly. She will never apologize for leaving Rumpelstiltskin: for that would mean being sorry she met and fell in love with Killian -- but she is sorry that she didn't take Bae with her initially, and that she was unable to go back for him even though she desperately wanted to.
Plot Concerns.
Bae is around six when Milah leaves with Killian, 14 when he goes through the portal.
How is his age being explained like if he's still come across Killian post-Milah death, and appears 14, but Milah is apparently alive when Orion is 17???
My suggestion (apologies if you've all worked something out already, just throwing this out there) : They have Orion a couple of years after they run off together, making him six years old when Bae goes through the portal at 14. Shortly after, they go back to get Bae but it's too late, he and Rumple are nowhere to be found and they are told Rumple is now the Dark One. They don't encounter Rumple at this point in time.
The Joneses sail the seas for several more years, then they encounter Rumple, who supposedly kills Milah.
As I don't know how Killian and Orion are eventually parted, I'm not sure how old Orion should be when this happens.
My other idea was, Bae looks 14 when he encounters Killian bc he's been in Neverland and hasn't aged -- but if Orion is 17 when Milah is killed, that would mean Bae had been in Neverland for like 10 yrs. And idk how realistic that is or not.
Basically, let me know what you guys have been playing it as and where you're willing to meet me on things. I personally would rather keep as close to canon timeline as possible and have Orion have been younger when Milah dies - possibly even the same age as Bae was parted from her (six) bc lol painful ironies.
Orrrrr just tell me hey new girl shut up no one cares and I can um just roll with whatever. I'm warning you now tho I love timelines. A lot. Obnoxiously a lot.
