Britney. She vows to be a virgin and promptly gives it up to a member of N'sync (this isnt where the bad taste ends, unfortunately) then she marries a guy (in a drunken stupor) that she could have actually had a good life with because he was a friend before their marriage, and they got it annulled 55 hours later because her daddy told her that since there was no prenup, he could ruin her. Then she steals and marries Mr Trailer Trash Daddy and gets pregnant, smokes and drinks, and is constantly watched by social services because she doesnt know the first thing about taking care of herself, let alone a child.
Jamie Lynn hasnt had any major relational screwups yet. although, judging by how perfectly shes imitating her big sister, that might not be in the far off future.
so lets give the stupid award to jamie lynn instead, for being a lemming in itty bitty cutoffs and stickers and string "tops" If shes lucky maybe she can land a catch like Federline for herself! Better yet, being the big philanderer that he is, Federline might just make himself available to be jamie lynns first of many grooms.