Did you ever think of that after all the women Sawyer conned and all the women he broke thier heart's,someone really broke his....
During lost Sawyer conned lots of women and broke their hearts.For example,Cassedi fell in amor with him and got hurt when he left herand coned her. And she's only one example...
However,on the island he fell in amor eith the wrong women.From all the women he fell in amor with Kate,who fell in amor 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 amor him back like he does,he waspunished for what he did.