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For decades, there’s been a certain relationship trope in movies that we haven’t exactly been a fan of, and that’s men being romantically involved with younger women. Now, we’re not saying that all these films are bad movies — honestly, we’ll watch Humphrey Bogart and Lauren Bacall any day. But because these types of romances have been so normalized, we really don’t often see enough stories about the opposite: women who have relationships with younger men. And when we do, we talk about them like they’re anomalies or somehow taboo — think The Graduate or Daniel Craig-led The Mother, in which older women pursue their daughter’s romantic interests.
In recent years, we’ve seen a positive shift in some depictions of women who pursue, date, or have relationships with younger men, even if it’s hardly the cinematic mainstay we’d like it to be. New additions to the genre like Something’s Gotta Give show that these dynamics don’t have to be any more complicated than when older men date younger women — which, as we’ve pointed out, happens so often in film that we’d struggle to round it down to a top 500.
From hidden gems like The Good Girl, starring 21-year-old Jake Gyllenhaal and 32-year-old celebrity crush Jennifer Aniston to the decidedly darker The Reader, starring Kate Winslet in her Oscar-winning performance, these movies all took a stab at showing the real-world Olivia Wilde-Harry Styles dynamic on-screen, for better or for worse. Read on to see which of your favorite actors have coupled up with slightly-to-much older ladies for a movie romance.
A version of this article was originally published on Oct 2021.