During ロスト Sawyer conned lots of women and broke their hearts.For example,Cassedi fell in 愛 with him and got hurt when he left herand coned her. And she's only one example...
However,on the island he fell in 愛 eith the wrong women.From all the women he fell in 愛 with Kate,who fell in 愛 with Jack.It's like a punishment for him for breaking lots of women's heart.Although she has feelings for him but she can never 愛 him back like he does,he waspunished for what he did.