Look, I understand your point and I shouldn't consider any woman being nice to me as flirting.... But in this particular case, she just asked me for my phone number yesterday so she could quote " get to know me better and continue the conversation over the weekend." We have odd work weeks and this is the start of our weekend.
I don't think there is any mystery about that part anymore. I had asked if she was seeing John and she said no, they are just friends.
As for John, he was denied for the role he really wanted to apply to for very dumb reasons and I am very upset for him. There is nothing I can personally do about improving his situation as the things he hates about our company are not within my or even my superior's control. He has told me he can't leave either as he can't find a job elsewhere.
I want to be supportive of John, but I am even trying to push it in this direction, its just going there on its own and I am currently not stopping it as she is an awesome person I would like to get to know better.
You are right though, there is no option where "I get the girl" and not burn bridges and not torch themental health of my coworker. Even if I said no, he will still be hurt as she is clearly not interested in him. Just to a lesser degree.
I know, such a breath of fresh air!