Everyone’s a little fascinated with the unconventional. So it’s no surprise that plenty of films have pushed the boundaries of the norm (and sometimes even of the appropriate or legal) to explore relationships that are outside of the box. While some of these May-December romances are entirely on the up and up, others definitely cross the line (we’re looking at you, Lolita). We’ve rounded up some of the most notable romances that portray relationships with significant age differences: some are sexy, some are a little shady, and some are just downright wrong.
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