Chris and Winia
As you may guess by its postion at the top, this is my favorite pairing in all of Scrapped Princess.

Why it works:
Chris and Winia have common ground.  They both grew up largely alone, and both felt jealous of the closeness Pacifica and her siblings had.  When Chris kidnapped Winia, the story of her life forced him to remember his own loneliness, once upon a time.  Winia was able to read Chris's jealousy, and made him lose his cool in his battle with Shannon (no mean feat).  Later, Chris saved Winia from the Peacemaker's attack on her village.  Obviously Winia made enough impression on Chris for him to send her a letter talking about the moon in the glass gorge that night (when he kidnapped her).  And he made enough impression on her for her to leave her town and go to see him, just because she thought he was lonely.  Even after being wordlessly snubbed at the gates to Chris's house, Winia continued to keep her optimism.

Why it doesn't work:
Class differences?  I don't think the Countess who adopted Chris would put up a fuss over it, though.  After all, remember how she spread the news of Winia's letter to Chris, making it out to be a love letter?  The only other reason I can think of would be that one or both of them 'belong with somebody else.'  I know I've heard arguments for Chris and Pacifica, but I don't really see it.

Why I like it:
From the moment Chris took Winia to the glass gorge, I fell in love with this pairing.  Something about the ordinary girl and the 'bad' boy, perhaps?  Winia's sweetness softens Chris, and she had the power to make him falter in a fight with her words of truth concerning him.  Some of the moments between these two (like their meeting in the capital and later, near the end of the show after Fulle died) absolutely sent a shiver down my spine.  The way their relationship begins is gold, too.  Falling for the guy who kidnapped you?  And the letters being passed back and forth . . . I just can't help but think how right it is.

A Happy Ending?

I got my way with this one ^_~  Though they had their ups and downs, the last episode reveals Chris in a new role . . . Winia's husband.  Yum.
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