I don't think Ben loved her, like everything else she was just a possession. Plus she betrayed him and that's a no no. Also, Ben doesn't strike me as someone who gives a damn when someone on the island dies.
I think you're spot on with his relationship with Juliet, he always seemed more fascinated by her, than in love. I do think Ben gives a damn about some people on the Island though, he's still not over Alex and she died 3 years ago at this point.
Alex was his "daughter" and as far as I can tell she's the only exception. I never saw him get weepy over anybody else. Heck his biggest bond was with John and when John died and Ben had to bury he him he was all snark.
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I really do think he'd be sad. I mean, the man had tears in his eyes when they said goodbye during (I believe) "The Man From Tallahassee."
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I wanna seeee.
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