Poly Pirate Crew Timeline
I should not have been allowed to do this rewatch. I am back on my poly pirate crew bullshit and I'm about to drag a bunch of new followers down with me if I have my way. :P
SO.
About three months before D2 (and 3 months after D1) the crew first forms. They're described as 'hardened mercenaries' 'cutthroats' and 'a bunch of scoundrels' but also as kids who were deemed not worth very much by the Isle. There are bumps and bruises in getting some of them into teamwork but overall, things go really well. Uma quickly inspires confidence by doing things like diving into the sea to rescue Gil or waiting at the mouth of a collapsing cave to make sure her entire crew gets out.
Over that three month interval, the crew not only makes major territory grabs (including Mal's former territory) and even begins to be taken seriously by some of the adults. They also start hanging out and spending most of their time together, so when it comes to doing things like making out as stress relief or going to places together, it's usually with each other. At some point it occurs that they're all pretty much dating each other but they have bigger things to worry about so it's not that big of a deal.
Descendants 2 goes down, Uma's missing for a whole year. Harry takes over and manages to hold down the fort but the crew is a mess without Uma and he knows it. Even people who don't hang around the crew like Ginny Gothel notice how close knit the crew is and can no longer imagine Harry without them. Harriet notes that getting Harry a VK Day application is pointless because he won't leave without his crew. They also note he's been miserable without Uma.
Descendants 3 goes down, Uma returns! The crew is elated but only for a moment. Uma has to tell them the gut punching news that the barrier is going to stay closed forever and they're all going to die on the Isle. Rather than dwell on that, she focuses them on preparing to protect the Isle as supplies dwindle and chaos breaks out. Obviously this crisis is averted by Mal letting down the barrier and setting them all free.
The crew is in Auradon now! They take about a semester to get caught up on educational requirement differences and their 'we're REASONABLY certain they won't destroy Auradon' stamp of remedial goodness. They make things official and enjoy both running wild and having actual DATING moments. During this time, they find an abandoned villa in Auradon that they claim as theirs (by hiding it from everyone else with magic). Then they're officially free to pursue their own interests and they all....split. Everyone is on their own for about a year. Uma's happy for them chasing their dreams but also devastated to lose them. Well, after that year, Drey calls a meeting in a warehouse to see everybody. Harry reveals he's spent that time fixing up the Lost Revenge to be seaworthy and now they can go wherever they want and do whatever they want. The crew gets back together and sets sail for about a year and a half (totally not doing revolutionary things to stop certain escaped villains from hurting kids or bringing down places like the Isle, nooooo).
Uma is invited to be in charge when Mal, Jay, Evie and Ben go off to do some alliance building. She accepts and her crew accompanies her back. Most of them settle the villa and get their 'living on land' ducks in a row, but about six get Uma's office ready and help her out (yes this is from the Merlin verse but IDC, I like it, so it happens here too. :P)
Once Mal and Ben return, Uma's crew goes back to the water. They return periodically but for the most part, they are now full time pirates. After a while they start considering themselves PRETTY MUCH married. During one of these visits back, Drey gets pregnant with the crew's first kid born during the relationship (Valor being born before hand) at about age 26. This kicks off the start of lots of kids. Does this stop them adventuring, treasure hunting or pirating? Absolutely not.
There's a lot of details to fill in in between these but this is the general gist of how I imagine that relationship going.
