Movies Like Older Women with Young Boys

If you liked Older Women with Young Boys (1985), a movie directed by Drea, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
My Awkward Sexual Adventure (2012)
★ 6.7/10
A hyper-repressed and schlubby accountant (Jonas Chernick) strikes a deal with a worldly but disorganized stripper (Emily Hampshire): he'll help her with her crushing debt if she helps him become a better lover.
2
A Good Old Fashioned Orgy (2011)
★ 5.8/10
A group of 30-year-olds who have been friends since high school attempt to throw an end-of-summer orgy.
3
Deep End (1971)
★ 7/10
London, England. Mike, a fifteen-year-old boy, gets a job in a bathhouse, where he meets Susan, an attractive young woman who works there as an attendant.
4
Out of the Blue (2022)
★ 5.9/10
After spending time in prison following an assault charge, Connor Bates now works in a library and spends his free time running, swimming, and trying to piece his world back together. When he meets Marilyn Chambers…
5
The Graduate (1967)
★ 7.6/10
A disillusioned college graduate finds himself torn between his older lover and her daughter.
6
Auto Focus (2002)
★ 6.4/10
A successful TV star during the 1960s, former "Hogan's Heroes" actor Bob Crane projects a wholesome family-man image, but this front masks his persona as a sex addict who records and photographs his many encounters…
7
The Good Girl (2002)
★ 6.2/10
A discount store clerk strikes up an affair with a stock boy who considers himself the incarnation of Holden Caulfield.
8
The Only Living Boy in New York (2017)
★ 6.3/10
When a young man learns that his overbearing father is having an affair, he tries to stop it, only to be seduced by the older woman as well.
9
Snack Shack (2024)
★ 7.4/10
Inseparable best friends AJ and Moose decide to run the local pool's snack shack after their plan to sell home-brewed beer goes down the drain. Things take a turn when they meet Brooke, an effortlessly cool lifeguard…
10
The Postman Always Rings Twice (1981)
★ 6.5/10
The sensuous wife of a lunch wagon proprietor and a rootless drifter begin a sordidly steamy affair and conspire to murder her Greek husband.
11
W.E. (2011)
★ 6.3/10
In 1998, an auction of the estate of the Duke and Duchess of Windsor causes great excitement. For one woman, Wally Winthrop, it has much more meaning. Wally becomes obsessed by their historic love story. As she learns…
12
One Hour Photo (2002)
★ 6.7/10
Sy Parrish has lovingly developed photographs for the Yorkin family since their son was a baby. But as the Yorkins' lives become fuller, Sy's only seems lonelier, until he eventually convinces himself he's part of…
13
Heatwave (2022)
★ 6.2/10
A woman's life takes an unexpected turn when she falls for her boss's wife. She must soon defend herself as she becomes entangled in a web of malice.
14
Strictly Sexual (2008)
★ 6.1/10
Two successful women, sick and tired of dating and relationships, decide to keep two young men in their pool house for strictly sexual purposes.
15
Careful What You Wish For (2015)
★ 6.1/10
A guy gets more than he bargained for after entering into an affair with the wife of an investment banker. Soon, a suspicious death and substantial life insurance policy embroil him in a scandal.
16
The Last Tycoon (1976)
★ 6.3/10
Monroe Stahr, a successful movie producer, pursues a beautiful and elusive young woman — all the while working himself to death.
17
Original Sin (2001)
★ 6.2/10
A young man is plunged into a life of subterfuge, deceit and mistaken identity in pursuit of a femme fatale whose heart is never quite within his grasp.
18
Good Luck to You, Leo Grande (2022)
★ 7/10
Nancy Stokes, a retired schoolteacher, is pretty sure she has never had good sex. Now that her husband has died, she is determined to take a tour of sexual vistas that until now she has only imagined. She even has a…
19
Focus (2015)
★ 6.9/10
Nicky, an accomplished con artist, gets romantically involved with his disciple Jess but later ends their relationship. Years later, she returns as a femme fatale to spoil his plans.
20
The Postman Always Rings Twice (1946)
★ 7.1/10
A married woman and a drifter fall in love, then plot to murder her husband.