The 6 Best May-December Romances on Film

Many of us end up dating a partner who is relatively close to us in age, but love – or sexual attraction – can span decades. We’re all used to male actors (and producers) preferring to star opposite progressively younger co-stars as they age, but every so often a genuinely excellent movie comes along that has something to say about that age difference. Here are, in our refined opinion, the six best films dealing with May-December romances that you can watch today!

6. Behind the Candelabra (2013)

Steven Soderbergh's Behind the Candelabra - Liberace on Stage

This biopic of Liberace could have been a great many things. In the hands of Steven Soderbergh (Oceans 11) and Richard LaGravenese (The Last Five Years), it manages to simultaneously talk about how relationships with extreme age disparity can also have an extreme power disparity and how straight America can bury its face in the sand rather than deal openly with queer culture. Scott Thorson (Matt Damon), visiting Las Vegas, is befuddled that seemingly no one can tell that Liberace (Michael Douglas) is gay. Thorson and Liberace are quickly taken with one another, and the film tracks their five-year relationship as fame and ego threaten to tear them apart. Not all of the romantic relationships on this list are necessarily healthy, and Liberace’s with Thorson certainly wasn’t, but Behind the Candelabra is nevertheless an insightful, tender, angry film.

Behind the Candelabra is available now on DVD and blu-ray, and members of Amazon Prime or HBO Go can stream it free online.

5. An Education (2009)

Lone Sherfig's An Education - Women Directors

Directed with grace and insight by Lone Scherfig (One Day), An Education adopts the memoir of Lynn Barber. In it, Carey Mulligan (Suffragette) plays a smart young schoolgirl seduced by Peter Sarsgaard (Blue Jasmine), who sweeps her away to night clubs and concerts before slowly revealing that – surprise – this adult man seducing a 16-year-old girl may be a bit shadier than he appears on the surface. Scripted by Nick Hornby, one of this generation’s more sensitive writers on the intersection of love and pop culture, this is the go-go-60’s coming-of-age story to Brooklyn‘s working class 50’s milieu, but both films are insightful and thoughtful about class and power. But really, the film doesn’t work without Carey Mulligan, a rare talent who can portray intelligent naivete, girlish maturity, thoughtful obsession. Seeing Mulligan navigate the tricky minefield of expectation, lust, culture, and class is a genuine joy, and An Education walks that line with ease.

An Education is available now on DVD and blu-ray, and to pay to stream On Demand. It is also currently free to stream for Amazon Prime members with a Tribeca Short List subscription.

4. The Diary of a Teenage Girl (2015)

Marielle Heller's Diary of a Teenage Girl - Women Directors 2

On some level, The Diary of a Teenage Girl should be far more off-putting than it is. Adapted from a graphic novel of the same name, the story follows Minnie (Bel Powley), a 15-year-old in 1970’s San Francisco who loses her virginity to her mother’s boyfriend (Alexander Skarsgård) and begins experimenting with her sexuality while courting the older man. The Marielle Heller-directed film understands how creepy Minnie’s relationship is, unlike Woody Allen’s Manhattan, but that doesn’t mean she tones down the the comedy or the character study. Bel Powley is particularly good here as she deals with a combination of need and disgust, obsession and revulsion, in a surprisingly sophisticated performance. The Diary of a Teenage Girl is a smart sexual coming-of-age with a sharp sense of humor, and it knows exactly what it’s saying about older men, younger women, and this particular time and place.

The Diary of a Teenage Girl is available now on DVD and blu-ray, and to pay to stream On Demand.

3. Harold & Maude (1971)

Hal Ashby's Harold and Maude

There are a lot of people out there who have never seen Harold and Maude. Hopefully this list will start correcting that, because this is a funny movie, albeit a dark one. While most movies portray relationships between younger men and older women as unhealthy, Harold and Maude has fun with the pairing between morbid 20-something Harold and his growing attraction to no-nonsense 79-year-old Maude. The story a sweetly low-key romcom in which two people who didn’t see much reason to live find a way to take some joy out of life, rather than just focusing on death.

Harold and Maude is available now on DVD and blu-ray from the Criterion Collection, and to pay to stream On Demand. It is also currently free to stream for Amazon Prime members with a Starz channel subscription.

2. Carol (2015)

Todd Haynes' Carol -- Rooney Mara and Cate Blanchett Meet at the Store

I’ve written extensively about Carol already, and I don’t see myself stopping any time soon. It’s that good. In it, a young shopgirl named Therese (Rooney Mara) meets Carol (Cate Blanchett), an older married woman with whom she strikes up an immediate rapport. The two come together at first in an unlikely friendship, but it quickly becomes apparent that both sides are interested in more. Carol, a more experienced lesbian whose best friend (Sarah Paulson) was her former partner, awakens something in Therese that had previously lied dormant. But Carol’s husband has other ideas, and soon it begins to feel like society itself – or at least the patriarchy in general – is arrayed against Carol and Therese’s newfound romance. We may be getting fewer romances on our big screens each year, but if those we get are even half as good as this one, that’s a trade-off I’ll happily take.

Carol is available now on DVD and blu-ray, and to pay to stream On Demand.

1. The Graduate (1967)

Mike Nichols' The Graduate - Smoking

Perhaps the most iconic May-December romance of all time despite a surprisingly small age difference between Dustin Hoffman and Anne Bancroft, The Graduate has stayed relevant for one reason: It’s really, really good. Benjamin Braddock is just finishing college, and he has no idea where to go from here. He mostly just spends time lounging in the pool… at least until he meets Mrs. Robinson, a sophisticated older woman with whom he begins an affair. But when he begins to fall in love with Mrs. Robinson’s daughter, Elaine, his life begins to get a lot more awkward – though, of course, no less formless. With amazing performances, beautiful editing, and one of the most iconic final shots in film history, The Graduate is the most fitting place to end a list like this.

The Graduate is available now on DVD and blu-ray from the Criterion Collection, and to pay to stream On Demand. It is also currently free to stream for Amazon Prime members with a Tribeca Short List subscription.



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