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Was treibt eine solch hübsche junge Dame dazu, mit einem Haufen Langweiler herumzuhängen?
Considering that the preposition mit should be followed by a dative form, I would be tempted to say Langweilern (Plural Dative) instead. I wonder why Langweiler is the correct word here? I suppose it is not the dative form.
It is "Haufen" (=pile) that is in dative, not the content of the pile. The content of something can be expressed with a genitive construction, as in this case.
