By request of the KBZ community, we’ve been asked to highlight the 25 best coming-of-age films featuring younger men with older women. This is another special edition article where we’ll look at various films from The Graduate (1967) to the early 1980’s ‘golden age of male jailbait films’ that included Private Lessons (1981) and My Tutor (1983) to recent films where young males come of age with an older female in No Hard Feelings (2023) and The Idea of You (2024).
Most of the films we’ll outline in this article are from our collections of Teen & College Comedy Films and Drama Films About Teens & Young Adults. Both of these collections include every teen drama and comedy from the last 50+ years and you can find some of these films listed in previous articles where we outlined The Best 1980’s Sex Comedies and lesser-known Teen Comedies by decade.
Before we dive into our rankings of these coming-of-age films we’re going to use some criteria to help define and refine our list. First, to be included on our list, the film must primarily focus on coming-of-age themes involving a romance or affair between a younger man and older woman. This will exclude films such as Animal House (1979), Caddyshack (1980), The Last American Virgin (1982) and American Pie (1999). While each of these films has strong coming-of-age themes, the younger male with an older female arc in each film is a minor subplot from Otter’s (Tim Matheson) fling with Mrs. Wormer (Verna Bloom) in Animal House to Finch’s (Eddie Kay Thomas) seduction by Stifler’s Mom (Jennifer Coolidge) in American Pie.
Second, we’re going to have to set both an age baseline and age range for films on our list. For our age baseline, we’ll set that at the early teen years. For our age range, we’ll include early teen years to early twenties. Though we’ll focus primarily on the teenage years, there are some great films that explore mature coming-of-age themes like Cha Cha Real Smooth (2022) and The Idea of You (2024) so we’ll be a little loose with the early twenties end range.
Third, we’re going to focus this list on larger age discrepancies between the younger man and older woman, so we’ll also exclude coming-of-age films that primarily focus on romances between a younger male teen and older female teen. This would affect coming-of-age films like Lucas (1986), Eight Days a Week (1997), The Girl Next Door (2000), The French Kissers (2009), Love at First Hiccup (2009), Love is the Word (2013), My Extraordinary Summer with Tess (2019) and Falcon Lake (2022). While all of these are great coming-of-age films (and we highly recommend checking out), they won’t be included on this specific list but will likely make one of our future lists highlighting some of the best overall coming-of-age films.
Fourth, though many of these coming-of-age films with young teen men and older women appeared during a wave of teen-focused films the early 1980’s, a good majority of these films aren’t very good. For every great subgenre film like Class (1983) there’s also a very bad film like Homework (1982). Though we’ll list most of these bad films below, some are better left to the annals of time (and your teenage memories).
Fifth, we’re also going to exclude films that, while focusing on coming-of-age themes, are often much more focused on a separate, stronger theme. These include:
- Films About Incest. Ma Mere (2004), Savage Grace (2007) and Grand Jeté (2022) are all coming-of-age films but the primary focus of the film is about incest between a mother and her son.
- Films About Infidelity. Affairs between an older woman and younger man are the main focus of The Good Girl (2002), A Good Lawyer’s Wife (2003), Queen of Hearts (2019) and Last Summer (2023). All of these films tackle themes of infidelity much more so than coming-of-age themes.
- Films About Murder Plots. They’re Playing With Fire (1984), Wicked Minds (2003), Beautiful (2009). Dirty Teacher (2013) and Careful What You With For (2015) are all examples of films with a romance between a younger man and older woman, but the main thread of these films involves murder.
- Films About Stalkers. Though the majority of stalker films involves an older male stalking a younger female, there are a few films featuring an older female stalking a younger male. Films such as Deep End (1971), Coffin Rock (2009), Bad Sister (2015) and The Boy Next Door (2015) do involve an older woman in a romance with a younger man, but these films focus on obsession and subsequent stalking as their main narratives.
- Reincarnation, Scandal and Medical Issues. Other films we reviewed for this list didn’t fit into a specific subgenre listed above but rather combined themes of coming-of-age, a disparate age-related romance and unique themes. Notes on a Scandal (2006) featured a romance between a male teen student (Andrew Simpson) and older female teacher (Cate Blanchett) but is much more about the subsequent scandal at the school. Reincarnation is the theme of Birth (2004) involving a woman’s (Nicole Kidman) deceased husband who has been reincarnated as a young boy (Cameron Bright). And Nitram (2021) does involve coming-of-age themes and a romance between the young Nitram (Caleb Landry Jones) and older Helen (Essie Davis), but the film is much more about the psychological deterioration of Nitram leading to the deadliest mass shooting in Australian history.
And sixth, we had to follow our rule for all of KBZ’s film listings where we only list films that have a 4.0/10 or higher rating and were released after 1970 (though we’ll make one exception for this rule to include a 1967 film that is a classic of this subgenre with our specific criteria).
Our complete list of Teen & College Comedies features over 794+ films from 1967– 2024 and our complete list of Drama Films About Teens & Young Adults features over 1,953+ films from 1955 – 2024. These collections feature all the best coming-of-age films throughout the past five decades so subscribe to our newsletter to get updated when we release more coming-of-age themed film lists.
We have embedded a compilation video of the Best Coming-of-Age Films – Younger Men with Older Women and more details on these films can be found in the list below. Note: We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to Amazon.com and affiliated sites.
Best Coming-of-Age Films – Younger Men with Older Women
Honorable Mentions: 40 Carats (1973), Coach (1978), Homework (1982), Norman Love Rose (1982), A Night in Heaven (1983), No Small Affair (1984), Devil in the Flesh (1986), A Tiger’s Tale (1987), Moondance (1995), The Man in the Attic (1995), My Teacher’s Wife (1995), Try Seventeen (2002), Uranya (2006), The Blonde with the Bare Breasts (2010), Cougars, Inc. (2011), The Dish & The Spoon (2011), The Cowards Who Looked to the Sky (2012), The Maid (2014), Dreamland (2016), Miss Stevens (2016), Breath (2017), Before the Dawn (2019), Dreamland (2019), Wild Seas (2022), Babygirl (2024) and Bridget Jones: Mad About the Boy (2025).
Rank 25-1:
#25 Private Lessons (1981) Where to Stream / Buy: Tubi
#24 Cha Cha Real Smooth (2022) Where to Stream / Buy: Apple TV+
#23 The Idea of You (2024) Where to Stream / Buy: Amazon
#22 Mammal (2016) Where to Stream / Buy: Apple TV+
#21 My Mistress (2014) Where to Stream / Buy: Amazon
#20 Tadpole (2002) Where to Stream / Buy: Amazon
#19 An American Affair (2008) Where to Stream / Buy: Amazon
#18 One Last Thing (2005) Where to Stream / Buy: Amazon
#17 My Tutor (1983) Where to Stream / Buy: Amazon
#16 No Hard Feelings (2023) Where to Stream / Buy: Amazon
#15 Gotcha (1985) Where to Stream / Buy: Amazon
#14 Year of Enlightment (1986) Where to Stream / Buy: YouTube
#13 Losin’ It (1982) Where to Stream / Buy: Amazon
#12 Weird Science (1985) Where to Stream / Buy: Amazon
#11 Saturday Night Fever (1977) Where to Stream / Buy: Amazon
#10
Loverboy
Plot: Delivering pizzas doesn’t pay much — especially when Randy Bodek (Patrick Dempsey) needs to earn enough to fund next semester’s college tuition. During a routine delivery, however, Randy meets a sexy older woman named Alex (Barbara Carrera). The pair become lovers, and soon she’s recommending Randy‘s services to all her unhappily married friends — just order a pizza with extra anchovies and tip well. But, as Randy soon learns, life as a professional gigolo can get pretty complicated.
KBZ’s Take: Though Loverboy was released at the tail end of the 1980’s, it’s a spiritual successor to many of the ‘male jailbait’ sex comedies that came before it. While many of those earlier films were focused on the shock value of a younger teen male with an older woman, Loverboy takes a more comedic approach of a younger man suddenly desired by much older women.
Patrick Dempsey would have his breakout moment in the TV series, Grey’s Anatomy, but for much of the 1980’s and 1990’s he was an underrated actor in cult classics such as Can’t Buy Me Love (1987) and Run (1991). Loverboy is one of his best early roles and is arguably his best comedic performance of his decades long career.
Additional Lists: The Best 1980’s Sex Comedies #19
Where to Stream / Buy: Amazon
#9
Vision Quest
Plot: After deciding he needs to do something meaningful with his life, high school wrestler Louden Swain sets out on a mission to drop weight and challenge the area’s undefeated champion, which creates problems with his teammates and health. Matters are complicated further when Louden’s father takes in an attractive female drifter who’s on her way to San Francisco.
KBZ’s Take: Vision Quest is one film we had an internal debate on as it fits in multiple subgenres from coming-of-age films to sports dramas. However, where the film won out for this list (and it’s ranking here) is that the entire film is centered around Louden Swain’s (Matthew Modine) coming-of-age romance with the older Carla (Linda Fiorentino).
Despite the film’s obvious similarities to The Karate Kid (1984) and it’s well known reputation as one of the best films about wrestling, it’s Modine and Fiorentino’s chemistry in the film that elevates it beyond similar subgenre fare.
Where to Stream / Buy: Amazon
#8
Rushmore
Plot: When a beautiful first grade teacher (Olivia Williams) arrives at a prep school, she soon attracts the attention of an ambitious teenager named Max (Jason Schwartzman), who quickly falls in love with her. Max turns to the father (Bill Murray) of two of his schoolmates for advice on how to woo the teacher. However, the situation soon gets complicated when Max’s new friend becomes involved with her, setting the two pals against one another in a war for her attention.
KBZ’s Take: Technically, there is no actual ‘romance’ in this film between teen student Max Fischer (Jason Schwartzman) and his older teacher Rosemary Cross (Olivia Williams). However, it’s a classic coming-of-age tale with Max’s antics escalating during his feud with Herman (Bill Murray) for Rosemary’s affection.
Many of the subgenre’s earlier films all followed the same formula when it came to a teenager’s crush on his or her teacher, but Wes Anderson flipped that formula on its head with one of the quirkiest, yet funniest, coming-of-age films.
Where to Stream / Buy: Amazon
#7
Malena
Plot: In 1941, Renato was 13 years old and although the world was at war, nothing ever happened in this sleepy village in Sicily. Until the day he discovered something that would change his life forever… Malna, the beautiful young war widow who was the obsession of every man and the envy of every woman. Because of her, Renato will come to learn all of life’s lessons and find himself in places he never could have imagined.
KBZ’s Take: Malena has similarities to another film on our list – Summer of ’42 (1971). Both films feature a woman alone (whose husband is away at war) and a teenager obsessed with the isolated beauty. However, while both films are primarily coming-of-age tales, Malena transitions into a much different film by its second and third act.
While the film is still about teen Renato’s (Giuseooe Sulfaro) infatuation with the older Malena (Monica Bellucci), it also focuses on themes of objectification of beauty and war-time treatment of perceived ‘outsiders’. It isn’t lighthearted subgenre fare like most films on our list, but it’s a film that will stay with you long after viewing.
Where to Stream / Buy: Amazon
#6
Class
Plot: Naive Midwestern prep student Jonathan (Andrew McCarthy) bonds with his more worldly roommate, Skip (Rob Lowe), who takes the small-town boy under his wing. At Skip’s urging, the inexperienced Jonathan is emboldened to seek out older women in the cocktail lounges of nearby Chicago, where he meets and beds the alluring Ellen (Jacqueline Bisset), who unfortunately turns out to be Skip’s mother. The division between the friends is further deepened when a cheating scandal engulfs the school.
KBZ’s Take: Unlike many of the other early 1980’s ‘male jailbait’ films, Class actually is a more realistic coming-of-age story and one of the best of its era. It’s entirely plausible that Jonathan (Andrew McCarthy) would meet and fall for Ellen (Jacqueline Bisset).
Though the remainder of the story is a bit predictable, it’s still engaging due to a stellar cast with McCarthy, Bisset, Rob Lowe, Cliff Robertson, John Cusack, Alan Ruck and Virginia Madsen. It’s also one of the better films of the subgenre to balance an adult theme with drama and comedy.
The film foregoes raunchiness to bring ‘class’ to the subgenre theme of young teens in love with older women. If you still haven’t seen this film, it’s one of the better films of the subgenre and highly recommended.
Additional Lists: Top Teen & College Comedies You Haven’t Seen – 1980 – 1984 #1, The Best 1980’s Sex Comedies #8
Where to Stream / Buy: Amazon
#5
5 to 7
Plot: A young writer begins an affair with an older woman from France whose open marriage to a diplomat dictates that they can meet only between the hours of 5 p.m. to 7 p.m.
KBZ’s Take: 5 to 7 is one of our personal favorite films of the subgenre and is a film we highly recommend checking out (especially if you like other subgenre films on this list). It’s a film that tackles mature coming-of-age films unlike other films on our list.
Whereas teen coming-of-age films deal with the transition of childhood to adulthood, coming-of-age films featuring a person in their early 20’s tend to focus on the various paths that adulthood provides. An example of these different themes can be found in The Breakfast Club (1985) compared to St. Elmo’s Fire (1985).
With 5 to 7, the focused theme is on finding the love of your life who happens to be much older, married, has children and is in an open marriage. How you might approach that situation, while falling deeper in love, is the unique aspect to the film that will resonate with anyone who believes in soulmates.
Where to Stream / Buy: Amazon
Plot: Over the summer of 1942 on Nantucket Island, three friends — Hermie, Oscy and Benjie — are more concerned with getting laid than anything else. Hermie falls in love with the married Dorothy, whose husband is an army pilot recently sent to the battlefront of World War II.
KBZ’s Take: Summer of ’42 is the best film on our list that balances multiple coming-of-age themes all at once. It has some comedy with typical teen coming-of-age antics, but it’s a much more powerful and dramatic film when it focuses on the emerging relationship of teen Hermie (Gary Grimes) and the older Dorothy (Jennifer O’Neill).
Like Malena (2000), Summer of ’42 is set during a wartime era. However, this film examines the emotional connection between Hermie and Dorothy and goes beyond typical teenage obsession. It’s a film as much about loss as it is about situations that can define someone’s life.
The film was very popular in 1971 and has endured as one of the best coming-of-age films for the last four decades. For younger viewers, this is a film you won’t want to miss as it’s one of the best of the entire subgenre.
Additional Lists: Top Teen & Young Adult Drama Film You Haven’t Seen (Part 1) #10
Where to Stream / Buy: Amazon
Plot: Ecstatic when his parents leave on vacation for a few days, high school senior Joel Goodsen (Tom Cruise) cuts loose with his best friend Miles. After an attempt at securing the services of a prostitute goes slightly awry, Joel hires gorgeous Lana (Rebecca De Mornay) for a night of delight. Stunned by the amount of Lana’s “bill” the next morning, Joel grows frantic after he crashes his father’s Porsche. In an effort to raise lots of money fast, a desperate Joel turns the house into a brothel.
KBZ’s Take: Risky Business is one of the more subtle Sex Comedies that tackles mature coming-of-age themes. Unlike other subgenre films of the era, the film passes on juvenile raunchiness to explore the relationship between Joel (Tom Cruise) and Lana (Rebecca De Mornay). The film doesn’t focus as much on the age difference between the two, as it elevates a typical coming-of-age sexual situation into one of business opportunities and partnerships.
Cruise had already established himself as an up and coming teen actor in Taps (1982), Losin’ It (1983) and The Outsiders (1983), and Risky Business was more or less his first starring role where he shines throughout as the teen who initially takes on more than he can handle. This was not only Tom Cruise’s breakout film but also helped launch the career of Rebecca De Mornay.
Additional Lists: The Best 1980’s Sex Comedies #4
Where to Stream / Buy: Amazon
#2
The Graduate
Plot: Benjamin, a recent college graduate very worried about his future, finds himself in a love triangle with an older woman and her daughter.
KBZ’s Take: We realize we’ll likely get some heat for putting The Graduate as #2 on our list as it’s generally considered the best film of the subgenre involving a younger teen with an older woman. And there is no doubt it is a great film that helped establish this specific theme of the subgenre and gave us the classic older woman archetype in Mrs. Robinson (Anne Bancroft).
However, the film is a bit dated, and we felt our #1 selection explored more current and relatable coming-of-age themes. With that said, The Graduate is a classic film of the subgenre and one that no fan of coming-of-age films should miss.
Where to Stream / Buy: Amazon
Plot: In Mexico, two teenage boys and an attractive older woman embark on a road trip and learn a thing or two about life, friendship, sex, and each other.
KBZ’s Take: Any of our Top 5 films on this list could easily be #1 but Y tu mamá también edged them all out based on a few factors.
It’s one of the best films of the entire subgenre to explore multiple coming-of-age themes including sex, the fragility of friendship, loss and entry into adulthood. And it does so in a raw and unfiltered manner.
There are also standout performances in the film from all three leads including Maribel Verdú and future stars Diego Luna and Gael Garcia Bernal. You can never take your eyes away from the interaction between the trio and never want it to end. This is a result of Alfonso Cuarón’s direction that turns a typical road movie into one where additional emotional layers reveal themselves as the story progresses.
While The Graduate (1967) established the subgenre theme of younger men with older women, Y tu mamá también reinvented the theme with a deconstruction of how various coming-of-age situations can be torn apart through a fantasized and taboo romance that teenagers are entirely unprepared for.
Where to Stream / Buy: Amazon
