A lot of what she's doing is worse than just loathsome: (Minor spoilers ahead)
She stole a psychiatrist's files on her patients and published them on a web site, just to hurt the psychiatrist.
She tricked a guy who makes investments for his clients to invest most of their money in a stock that she knew was going to lose most of its value, just to hurt that guy.
In both cases, she really hurt the clients of the person she was actually after. And there were a lot of them. I wonder how many people were put out of a job, lost their lives' savings, lost their marriages, were driven into severe depressions, and/or suicide. More recently, she just told a pregnant girl who thinks that "Emily" is her best friend that her boyfriend isn't the father of the baby. That's not nearly as bad as the other two things I mentioned of course, but it's remarkable because she did it to a person who loves her. She is a truly horrible person, but the show is still pretty entertaining.moreless
Thank you. That was one of the two I got wrong. Sam was the first option I ruled out, because those legs seemed to belong to a shorter person than Jared Padalecki. (The other one was the one with the skull. I couldn't really imagine that nose on that guy's face. I guess I haven't been observing him closely enough, or not recently enough or something).
Umm, number 9 of 10 in the "clue me in" (well the one i got, anyway), was of DEAN Winchester, not Sam. Now Jared Padalecki did play a Dean, but in that other show he didn't chop monsters heads off, he just got his heart broken by a girl suffering from 'bad boy' symptoms.