Personally my nomination is:
(SHOW ME THE ATROCIOUS SCRIPT!!) Jerry Maguire
I actually left a first date with a guy I quite liked just to get out of the cinema to avoid watching any more of this awful film. In it Tom Cruise leaves his confident business-woman fiance who is bisexual (eww!) and offers him a threesome (guys hate threesomes apparently!) and sets up with his single-mum secretary (don't worry she's widowed, not divorced! Unlike Renee Zellweger who plays her...) who lives with her sister (childless, divorced and super-miserable). There's a scene where Tom and the secretary are out on the town and you see the divorced sister at a "divorced women's club" (are there such things? I find none on Google, possibly because divorced women are able to participate in normal society and don't need a special club) sat around complaining about their ex-husbands (if there were such clubs would they do this? couldn't they go drinking or join salsa classes?) and then sat alone smoking (evil! evil!) in a darkened kitchen while ms. widowed laughs with TC in the driveway.
Any more nominations?