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Maybe it's just me, but I think the most interesting route they could have taken this Kyou/Tomoya After Story romance is forking off to different storyline at the point where she is introduced as Ushio's teacher.
From there, she and Tomoya could start keeping in contact under the guise of keeping him up to date with Ushio at school or "emergencies". Then they'll start meeting together, having that whole "it's complicated vibe" before they finally start dating, and she'll act as something of a stepmother/friend to Ushio (totally different from the chemistry between her and Fuko, btw). Along the line, things would get complicated, "I'm still thinking about Nagisa while I'm dating you", blah blah blah.
It seems very vanilla on paper, but I'm picturing this scenario very vividly and it seems like the most structurally sound approach to a Kyou After based on the series canon. I'd completely rule out marriage, though, as it'd seem way too hokey and unrealistic for Tomoya to have moved on that quickly and for them to have a "happily ever after" considering all that happened....bs.
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