I caught that look too. At the time, I couldn't decide if it was intentional, or just bad acting. If it was intentional, I suspect it's a nod to her mental instability, rather than some convoluted plan to go after his off-island money.
My guess is that later this season, she will turn out to be an obsessive, jealous, paranoid stalker. Moreover, while in the hospital, she created a complex fantasy life for her and Hurly; which we'll get to see.
This speaks to two "Things you wouldn't know without the movies":
1) Women who pursue men first, are insane.
2) Short, husky guys just can't get a break.
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Building an artificial intelligence that appreciates Mozart is easy. Building an A.I. that appreciates a theme restaurant is the real challenge - Kit Roebuck - Nine Planets Without Intelligent Life
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