During lost Sawyer conned lots of women and broke their hearts.For example,Cassedi fell in cinta with him and got hurt when he left herand coned her. And she's only one example...
However,on the island he fell in cinta eith the wrong women.From all the women he fell in cinta with Kate,who fell in cinta 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 cinta him back like he does,he waspunished for what he did.