I think we need to mix this up a bit...
First you piss in her drink, every single time she leaves the room... I don't care if you don't have to "go", just do it anyways. Secondly, ruin most of her clothes with some scissors... but do it so they're unwearable, and not "creatively fashionable". I hate that shit. Third, take some pictures of her when she doesn't suspect it... naked probably, put them up on a website (I suggest Rate My Body.com, as I have had some previous experience with it

) then email geeks telling them about it. Next you buy her lots of things to make up for it and gain her trust. Then you stab her in her sleep, in front of her boyfriend while she's wearing granny undies.