In contrast to the common trope of older men and younger women in Hollywood, there are several movies where women romance younger men, referred to as “May-December romance.” Below are 10 movies that showcase such relationships.
The Lifeguard (2013)
is a thought-provoking drama that follows Leigh, a 30-something former lifeguard turned journalist, who returns to her hometown to escape the pressures of adulthood. While there, she falls for a much younger teenage boy named Little Jason, and they begin a steamy romance that quickly becomes an affair. As their relationship intensifies, Leigh’s life spirals out of control, leading to some unexpected events. With great performances by Kristen Bell and David Lambert, “The Lifeguard” is a powerful exploration of the complexities of love, youth, and the search for meaning.
Where to Watch: “The Lifeguard”
- Streaming: You can stream “The Lifeguard” on fuboTV, Paramount Plus Apple TV Channel, and Amazon Prime.
- Free with Ads: Watch for free with ads on The Roku Channel, Crackle, Popcornflix, Pluto TV, and Freevee.
- Rental/Download: Rent or download on DIRECTV online.
The English Teacher (2013)
Julianne Moore stars as Linda Sinclair, a high school English teacher who takes an interest in a former student, Jason Sherwood, who returns to town after a failed career as a playwright. Determined to help Jason achieve his dreams, Linda mounts his play with the help of the school’s drama department. As they work together, Linda and Jason begin to develop feelings for each other, leading to a complicated and emotional romance. With great performances by the entire cast, “The English Teacher” is a charming and heartwarming romantic comedy that will leave you feeling good.
Where to Watch: “The English Teacher”
- Streaming: You can stream “The English Teacher” on Amazon Prime Video, fuboTV, and Fandor Amazon Channel.
- Free with Ads: Watch for free with ads on Peacock, Peacock Premium, VUDU Free, Tubi TV, Redbox, Crackle, Popcornflix, Pluto TV, and Freevee.
The Mother (2003)
“The Mother” tells the story of May, a middle-aged grandmother who lives a quiet life with her husband, Toots, in northern England. When Toots suddenly dies while their children are visiting, May falls into a deep depression and a sense of isolation. In an attempt to fill the void in her life, May takes refuge in the arms of Darren, a burly handyman who is half her age and married. To make matters even more complicated, Darren is also sleeping with May’s daughter, Paula. As May embarks on this illicit and unconventional affair, she begins to confront the complexities of love, loss, and aging. Anne Reid delivers an understated yet powerful performance as May, while Daniel Craig is enigmatic and convincing as the captivating Darren. “The Mother” may not be the best “Older Woman Younger Man” movie, but it is known for its standout performances and unusual premise.
Where to Watch: “The Mother (2003)”
- Streaming: “The Mother (2003)” can be streamed on Amazon Prime in select locations. Please note that availability may vary by region.
I Am Love (2009)
“I Am Love” is a cutting-edge melodrama that explores the passions and desires of the wealthy Recchi family in Milan. The story revolves around Emma, the wife of the patriarch Tancredi Recchi who is set to inherit his family fortune. Emma’s life takes an unexpected turn when she stumbles upon Antonio, her son’s best friend who is a talented chef. Emma quickly becomes enamored with Antonio and the two begin an intimate and physical relationship. As Emma’s infatuation with Antonio grows stronger, she begins to question her own identity and her place in the Recchi family. Tilda Swinton delivers a standout performance as Emma, drawing us into her world of forbidden love and self-discovery. “I Am Love” has been praised for its stunning visuals, compelling storytelling, and timeless themes of love, power, and self-actualization.
Where to Watch: “I Am Love”
- Streaming: Amazon Prime Video, Hoopla, DIRECTV, Magnolia Selects
- Free with Ads: VUDU Free, Tubi TV, Pluto TV
- Rental: Amazon Video, Google Play Movies, YouTube, Vudu, Apple TV, Microsoft Store
- Download: Apple TV, Amazon Video, Google Play Movies, YouTube, Vudu, Microsoft Store
Mammal (2016)
“Mammal” is a powerful and emotionally charged film that explores the themes of love, grief, and family. Margaret’s son is missing, presumed dead, and she takes the news without much apparent emotion. As she struggles to come to terms with her loss, Margaret befriends Joe, a shiftless teenager living on the streets of her unsavory borough. Margaret offers Joe a bed, board, and a degree of mothering, and the two form a deep and complex relationship that takes on a distinctly Oedipal quality. The film explores the intensity and complexity of the bond between a mother and a child, and how that bond can be transformed and redefined in unexpected ways. Rachel Griffiths and Barry Keoghan deliver powerful and nuanced performances that create a rock-solid center to this delicately handled immersion in love and grief. “Mammal” is a tense and poignant film that will leave a lasting impression on viewers.
Where to Watch: “Mammal (2016)”
- Streaming: Not available for streaming.
- Rental: You can rent “Mammal (2016)” on Google Play, Plex, prmovies, Amazon Prime Video, and iTunes.
- Download: Not available for download.
Bull Durham (1988)
“Bull Durham” is a classic sports comedy-drama film directed by Ron Shelton. The film stars Kevin Costner as a veteran minor league baseball player, who is tasked with mentoring a young pitcher “Nuke” LaLoosh, played by Tim Robbins, on and off the field. As the season progresses, the two men become romantically involved with the same woman, Annie, a baseball devotee who each year takes her pick of players from the Durham Bulls. Susan Sarandon delivers a stand-out performance as Annie, a gorgeous and witty woman who challenges both men on and off the field. The film provides a humorous and insightful look into the world of baseball and the human relationships that shape it.
Where to Watch: “Bull Durham”
- Streaming: Max, Spectrum TV, Prime Video, Vudu, Apple TV, Redbox, Hulu, HBO.
- Rental/Purchase: Amazon, iTunes, Google Play, Microsoft Store, YouTube, AMC on Demand.
How Stella Got Her Groove Back (1998)
Based on Terry McMillan’s semi-autobiographical novel, “How Stella Got Her Groove Back” is a romantic comedy-drama directed by Kevin Rodney Sullivan. The film follows Stella, a successful 40-year-old San Francisco stockbroker and single mother played by Angela Bassett. In desperate need of a break, Stella takes a trip to Jamaica, where she meets a 20-years-younger man, Winston, played by Taye Diggs. Despite their age difference, the two fall in love, leading to a heartwarming and boundary-breaking relationship. The film provides a refreshing perspective on love, aging, and interracial relationships.
Where to Watch: “How Stella Got Her Groove Back”
- Streaming: fuboTV, MGM Plus Roku Premium Channel, MGM Plus
- Free with Ads: Tubi TV.
- Rental/Purchase: Apple TV, Amazon Video, Google Play Movies, YouTube, Vudu, Microsoft Store, DIRECTV online, AMC on Demand.
Dreng (2011)
“Dreng” is a Danish coming-of-age film directed by Peter Gantzler. The film follows an 18-year-old boy who has just graduated from high school and is working at a summer job. He is seduced by a 36-year-old single mother, Sanne, played by Lene Maria Christensen, and soon finds himself drawn into a world of sensuality and an intense love affair that forces him to confront his newly discovered sides. The film portrays the realistic experiences and struggles of the characters and their complex relationship, leaving viewers wondering if the young man will be able to question and review his decisions as he navigates through his newfound passions.
And While We Were Here (2012)
“And While We Were Here” is a romantic drama film directed by Kat Coiro. The film stars Kate Bosworth as a married woman named Jane, who travels to the island of Ischia with her husband, a musician, to work on a writing project. While there, Jane becomes involved in an affair with a much younger man, played by Iddo Goldberg. The film provides a stunning visual feast for viewers, showcasing the beauty of the island, its classical music, score, and fashion sense. The film attempts to mimic Italian Neo-realism, and Bosworth delivers an affecting performance as a woman caught between two worlds, trying to make sense of her emotions and desires.
Where to Watch: “And While We Were Here”
- Streaming: Hoopla, True Story
- Free with Ads: Peacock, Peacock Premium, YouTube Free, Crackle, Pluto TV.
- Rental/Purchase: Redbox, Apple TV, Amazon Video, FlixFling online.
5 To 7 (2014)
“5 to 7” is a romantic drama film directed by Victor Levin. The film stars Anton Yelchin as Brian, a struggling young writer who meets a French middle-aged lady, Arielle, played by Bérénice Marlohe. Arielle is married to a diplomat named Valery, and both of them realize they are romantically attracted to each other. Arielle reveals that every day between 5 and 7 in the evening, she and her husband are allowed to have an affair with anyone, as long as it is confined within those time limits. The film explores the complexity of relationships and the different forms of love that exist in the world.
Where to Watch: “5 to 7”
- Streaming: AMC+ Amazon Channel, AMC+ Roku Premium Channel, DIRECTV
- Free with Ads: Tubi TV
- Rental/Purchase: Apple TV, Amazon Video online
- Download: Apple TV, Amazon Video, Google Play Movies, YouTube.
The Piano Teacher (2001)
This movie is a dark psychological thriller that explores the complicated relationship between Erika Kohut (played by Isabelle Huppert), a piano professor at the Vienna music conservatory, and her younger student, Walter (Benoît Magimel). The film is based on a controversial novel by Elfriede Jelinek, and it is not an easy one to watch. The story is disturbing, exploring themes of power, control, and desire, as Erika and Walter engage in a sado-masochistic relationship that ultimately leads to tragedy. Huppert delivers a stunning performance as the troubled and repressed Erika, and Haneke’s direction is masterful in its exploration of the human psyche.
Where to Watch: “The Piano Teacher”
- Streaming: Max, Criterion Channel
- Rental/Purchase:
- Buy (Download): Amazon Video, Google Play Movies, YouTube, Apple TV
- Rent: Amazon Video, Google Play Movies, YouTube, Apple TV online
The Reader (2008)
“The Reader” is a powerful film that deals with the complexities of a young man’s coming-of-age in the arms of an older woman who turns out to be a former concentration camp guard. The film is set in two different timelines, one in which the two characters meet and fall in love, and another in which they meet again years later in a courtroom. Kate Winslet gives a haunting and unforgettable performance as the enigmatic and existentially decimated woman, and the film is a beautifully flawed masterpiece that explores the nature of guilt, shame, and redemption.
Where to Watch: “The Reader”
- Streaming: Amazon Prime Video, Hoopla
- Free with Ads: VUDU Free, Tubi TV
- Rental/Purchase:
- Rent: Apple TV, Amazon Video, Google Play Movies, YouTube, Vudu, Microsoft Store, Redbox, DIRECTV online
- Download: Apple TV, Amazon Video, Google Play Movies, YouTube, Vudu, Microsoft Store, Redbox, AMC on Demand, DIRECTV.
The Rebound (2009)
“The Rebound” is a romantic comedy that follows a 40-year-old divorcee named Sandy (played by Catherine Zeta-Jones) as she attempts to create a new life for her family in New York. Along the way, she meets a 25-year-old good-looking babysitter named Aram (Justin Bartha), and sparks fly between the two. Despite the fact that the movie follows a familiar formula, it has its moments, and Zeta-Jones delivers a solid performance as the cradle-robbing businesswoman.
Where to Watch: “The Rebound”
- Streaming: Starz Apple TV Channel, Hoopla, Starz, DIRECTV, Starz Amazon Channel
- Free with Ads: The Roku Channel, VUDU Free, Tubi TV, Pluto TV, Freevee
- Rental/Purchase:
- Rent: Amazon Video, Google Play Movies, YouTube, Vudu, Microsoft Store, Apple TV online
- Download: Amazon Video, Google Play Movies, YouTube, Vudu, Apple TV, Microsoft Store.
Secret Love: The Schoolboy and the Mailwoman (2005)
This movie tells the story of a schoolboy who falls in love with a 37-year-old mailwoman. The two are from different social classes, and she is married, making their relationship even more complicated. The subject matter is interesting and fresh, exploring what happens when love goes madly for someone, regardless of social differences. The film is well acted, and the story is both moving and thought-provoking.
Adore (2013)
“Adore” is an experimental movie that tells the story of two older women, Lil (Naomi Watts) and Roz (Robin Wright), who fall for each other’s sons. The movie is based on Doris Lessing’s “The Grandmothers,” and it has a very unconventional storyline. The movie is thought-provoking and explores themes of love, desire, and family dynamics. The performances by Watts and Wright are excellent, and the movie is well worth a watch for those who are open to unconventional storytelling.
Where to Watch: “Adore”
- Streaming: Hoopla
- Rental/Purchase:
- Buy (Download): Apple TV, Amazon Video, Google Play Movies, YouTube, Vudu, Microsoft Store, Redbox, DIRECTV, AMC on Demand
- Rent: Amazon Video, Microsoft Store, Apple TV, Google Play Movies, YouTube, Vudu, Redbox, DIRECTV online
Unfaithful (2002)
“Unfaithful” is a thriller that explores the consequences of an affair between a married woman, Connie (Diane Lane), and a young bookseller named Paul (Olivier Martinez). The movie is famous for its steamy love scenes and nudity, but it is also a well-crafted thriller that explores the psychology of infidelity. Lane delivers a powerful performance as a woman torn between her desire for Paul and her loyalty to her husband, and the movie is a must-see for fans of erotic thrillers.
Where to Watch: “Unfaithful”
- Streaming: Hulu
- Rental/Purchase:
- Buy (Download): Apple TV, Amazon Video, Google Play Movies, YouTube, Vudu, Microsoft Store, DIRECTV, AMC on Demand
- Rent: Apple TV, Amazon Video, Google Play Movies, YouTube, Vudu, Microsoft Store, DIRECTV, Spectrum On Demand online
In the House (2012)
“In the House” is a clever, wickedly teasing reflection on the creative process, mentorship, and the power of fiction to create alternate lives and identities. The film follows a precocious student who infiltrates a classmate’s family and submits stories about them for a class. The teacher is shocked at first, but quickly becomes complicit in the story, even as it crosses dangerous territory. The film presents a charged atmosphere of dangerous sensuality and subversive humor that puts its French writer-director on the map. As the story progresses, the viewer is put in the same position as the characters. Although the film seems to run out of places to go at times, for most of its running time, it’s a deliciously clever divertissement.
Where to Watch: “In the House”
- Streaming: Fandor Amazon Channel
- Rental/Purchase:
- Buy (Download): Kino Now, Apple TV, Amazon Video, Google Play Movies, YouTube, Microsoft Store
- Rent: Apple TV, Amazon Video, Google Play Movies, YouTube, Microsoft Store, Kino Now online
Notes on a Scandal (2006)
“Notes on a Scandal” is a dynamic and sensual success company that ultimately leads to no one succeeding in the end. The film follows Cate Blanchett’s free-spirited art teacher, Sheba Hart, who sleeps with a 15-year-old student. However, it’s her friendship with a nosy co-worker that leads to her being arrested for the affair. The older woman, played brilliantly by Judi Dench, is shocked at the extent of the treachery, and the film explores the consequences of keeping secrets. Although it’s a sensual picture, it can also be scary at times. Blanchett’s performance as the naive teacher who realizes the wrong she’s done is outstanding.
Where to Watch: “Notes on a Scandal”
- Rental/Purchase:
- Buy (Download): Amazon Video, Google Play Movies, YouTube, Vudu, Microsoft Store, DIRECTV, AMC on Demand
- Rent: Amazon Video, Google Play Movies, YouTube, Vudu, Microsoft Store, DIRECTV online
Queen of Hearts (2019)
“Queen of Hearts” is a powerful and suspenseful film that delves into the consequences of an affair. The movie follows Anne, a successful lawyer and doting mother, who puts both her family and career at risk when she embarks on a relationship with her young stepson. The film deftly presses all the buttons to fuel our curiosity about how far things are going to go and what the consequences will be. As events turn much darker, the well-managed pace and a certain sense of integrity remain paramount even as shocking facets of Anne’s character are revealed.
Where to Watch: “Queen of Hearts”
- Streaming: Viaplay
- Free with Ads: The Roku Channel, Plex, Tubi TV
- Rental/Purchase:
- Rent: Google Play Movies, YouTube, Apple TV online
- Download: Apple TV, Google Play Movies, YouTube
A Short Film About Love (1988)
The way Kieslowski manages to portray the sheer tenderness of love here is simply beyond words. The film explores the relationship between a younger man and an older promiscuous woman whom he spies on from his window. She does not believe in love and is way beyond the naivety of a teenager who thinks he’s in love but is only infatuated with her. Kieslowski eventually grounds his story in the unexpected epiphany Magda experiences through the younger man. See this lyrical and affecting tale, and you’ll be moved to reconsider your own views on the subject. Moreover, it remains one of the best romantic films ever made.
Where to Watch: “A Short Film About Love”
- Streaming: Criterion Channel
