Ashley and Sydney would never get together in the original context of Vagrant Story.
They have known each other for like a day. The majority of that day was 1) Sydney screwing with Ashley’s mind, 2) Sydney being half-dead, and 3) Sydney not actually talking to Ashley…
Ashley and Sydney spend a week together, alone, between the time Lea Monde falls and Sydney returns to the Duke. Whether they “hook up” or not during that time is up to speculation, but it’s far from unfeasible.
Hee~ <3 This debate again~ <3
One of my oldest pieces of headcanon is that Ashley forges blunt fingers for Sydney between the destruction of Lea Monde and the final meeting with the Duke.
…oh that’s a cute headcanon. ; u; AND LET IT BE KNOWN that I actually do ship it—I just think it needs to be handled/developed carefully because of all the things that’d stand AGAINST it.