Silena is such a fun character to ship because she mixes tons of different kinds of fun opportunities : she's kinda a villain, she's super sweet but can kick-ass when needed, you can easily make her survive TLO or make her live in Elysium or...send her on Calypso's Island! Having Silena sent there after her fight against the Drakon is so interesting!

Just imagine her ending up there, with her face half covered in acid, so Calypso wouldn't even take the time to wonder what a girl did there, she would immediately tend her wounds and take care of her. I then easily see them being friends for a long period of time before feelings come in (they both just had to say goodbye to another love after all). But once the raft would come, I'm not sure : Silena could stay, but I don't see her as the kind to be ok with never seeing her friends and her family ever again.

And that's where Clarilenalypso or Charlenalypso could come in ! With Clarisse or Charles coming to her rescue after months of researches ! And after the awkwardness died down, they would help Calypso adapt back to the world, and grow closer to the point where they'd fell in love with her too, or would just be close enough to accept to both be Silena's partners!