- Why they could get together: After the deaths of Shannon and Nadia, Sayid could use a lady in his life, and Kate is still sad from the loss of Sawyer to Juliet. She's running around with Flocke's crew now, so it seems possible that these two could eventually get to knocking boots.
- Why they shouldn't: Both characters need someone a little more genteel to balance them out. Putting these two together just seems like a recipe for a badass, who-can-outdo-who disaster — the illegal, torture kind. Not to mention Sawyer would probably get himself killed if he ever tried to take Freckles back.
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