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