Since launching a video I made about love as an ageless and free agent — see below — I’ve been asked many times about films I recommend where the woman is the older one in the relationship.If you would like to watch my video, click here.

So let’s go. It seems that the only film people know is The Graduate, which is a classic and I love it, but it is definitely not the only one. Also, the relationship between 21-year-old Benjamin and middle-aged Mrs Robinson is pretty dysfunctional and is more of an experience than a real, loving relationship between two people who are in love.

So I have created a small list of films that mix functional and loving relationships between an older woman and a younger man. Some are romantic, some are complicated, some are downright disturbing — but they all have something interesting to say about age, attraction and relationships.

 

In the Bedroom (2001)

I chose it because it stars Marisa Tomei. She is one of those actresses I wish I could see more of because she is not just a photogenic darling but believable in everything she does.

A New England couple’s college-aged son dates an older woman who has two small children and a violent ex-husband who will do anything to stop them seeing each other.

It isn’t a conventional romantic film, but the relationship is central to the story and the consequences are anything but simple.

Prime (2005)

A career-driven professional from Manhattan is wooed by a young painter, who also happens to be the son of her psychoanalyst.

She is 37 and he is only 22, but they do fall in love and enjoy a real relationship. Of course, the fact that his mother is the woman’s therapist makes everything considerably more complicated.

The Graduate (1967)

The Graduate is a classic, but the relationship between Benjamin and Mrs Robinson is dysfunctional rather than a great example of two people simply falling in love.

Benjamin is 21, Mrs Robinson is considerably older, and their affair is tangled up in boredom, manipulation, dissatisfaction and the expectations of the world around them.

Still, it belongs on this list because it is probably the film that introduced several generations to the idea of the older woman/younger man relationship.

 

Brody-The-Graduate-1200.jpgThe Graduate is a classic but the relationship between them is dysfunctional

The Rebound (2009)

In New York City, a single forty-something mother going through a divorce captivates her new neighbour, a charming 25-year-old man who is far more mature and stable than her ex.

Fun, easy watching and, hey, when it’s love, it’s love — not age.

The Piano Teacher (2001)

This is a Michael Haneke film, so no light-hearted film here, but a very good film indeed.

Isabelle Huppert is her fabulous self as a repressed and deeply troubled piano teacher who is romantically pursued by her young student.

No easy watching. You have been warned!

Malizia (1973)

This is a great film, although don’t expect romantic love between any of the protagonists because they are all pretty dysfunctional. I’m including it here because I loved watching it.

I miss these types of films coming from Italy. These days it is all about “look at us, look how beautifully we can do beautiful shots.” Back then, the Italian masters were trying to impress no one and, boom, fantastic films that have made it into cinema history were created.

Malizia is the story of a beautiful housekeeper who becomes a romantic attraction to a widower and his three sons. She is more naive and innocent than the three young men put together, and they take advantage of her.

Brief Crossing (2001)

OK, you probably know I love French cinema, and this one was directed by one of my favourite female directors, Catherine Breillat.

A young French man and an older English woman spend one night together on a ship. A brief fling with no future, but these two seem to love the very fact that whatever they have is temporary and brief.

In any case, we all know that nothing is forever in life!

Good Luck to You, Leo Grande (2022)

And here is a much more recent addition to the list.

Emma Thompson plays Nancy, a 55-year-old widow who hires a much younger sex worker, Leo Grande, played by Daryl McCormack. What begins as a very specific arrangement gradually becomes something much more interesting: a genuine human connection between two people who are not supposed to fit the conventional idea of a romantic couple.

What I particularly like about this film is that it isn’t really about whether an older woman can be attractive to a younger man. It takes that question almost for granted and concentrates instead on intimacy, insecurity, ageing, desire and the possibility of discovering something about yourself later in life.

Emma Thompson and Daryl McCormack were both nominated for BAFTAs for their performances, while Thompson also received a Golden Globe nomination.

And that, really, is what I like about these films. The age difference is interesting, but it doesn’t have to be the whole story.

After all, why should love have an expiry date?