From Gen-X to Gen-Y: a journey in film

In search of  a credible female protagonist from Reality Bites to Frances Ha

Clockwise from top-left: Stills from Reality Bites (1994),
 Kicking and Screaming (1995),
Frances Ha (2012) and Damsels in Distress (2011).

Why do nice guys finish last?

The question contained in the title is a recurring theme in the films of Whit Stillman, which are largely autobiographical. With the release of Damsels in Distress (covered in these articles by The Atlantic, Wall Street Journal and The New Yorker) late last year after a thirteen year hiatus, it seemed befitting to relive some of the most memorable moments from his previous work. Even the initial sampler to Damsels, which can be viewed here, demonstrates the actual "problem" of female attraction to the dark male character. By reviewing what went before, we can probably shed some light on the topic at hand.

In this first clip taken from the Oscar-nominated Metropolitan (1990), we can get a flavor for Stillman's comedy of manners. As Nick Pinkerton in The Village Voice put it,  the film presents us with

the milieu of its writer-director—Preppie, Yuppie, Urban Haute Bourgeoisie—and treated it, not as something to be pilloried or taken for granted, but as a suitable subject for his characters' study, even defense ... It applied the emotional delicacy of the 19th-century courtship novel to the sexual revolution's aftermath—for Stillman, something more ambiguous and disorienting than the accepted version of escape from barren, pre-orgasmic Puritanism.