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Those answers were ridiculous, couldn't Celeste see the future results from the actions they would take? Though all of them could potentially be happy depending on choices, some would be happier than others. So she didn't actually give him an answer she just evaded the question.
The same about improving their lives. For instance, even Setsuna could see that if Minako valued love more than a long live then he would make her a lot happier than otherwise, and half a dozen children would be an improvement compared to more than a millennium alone, and being forced to only have one child.
And Setsuna herself would certainly be happier, than she has been on her lonely vigil.
Incidentally, the only one I shipped was Setsuna, she seemed to actually care about Grey, and showed a degree of consideration.
I'm just left disappointed after such a downer ending, having him be a slave to duty and Serenity, the woman who came across as a bigger bitch than the enemies in this story, with her only moment of acting somewhat nice was while she was a mindwammied Djinn.
"That's pretty much the end of Grey, a touch of realism here. Stuck in a relationship that the Silver Crystal couldn't bring love back into (Sorry, Sky, but i just cannot see anything less than significant rewriting of the character by mind control magic ever putting something close to love or trust back in that relationship."
Well, then have him refuse his duty? After all that's happened to him, why would he want to be anywhere near Serenity and the other Senshi?
It's sad that the author thinks unhappiness is necessary for a story to feel realistic, when there are actually women he could easily have been happy with, without his personality needing to be overwritten.
Nebula did have feelings for Pluto after all.