Most Popular "Older Woman Younger Man Relationship" Titles
- Movies or TV
- IMDb Rating
- Instant Watch Options
- In Theaters
- On TV
- Release Year
1. The Grand Budapest Hotel (2014)
R | 99 min | Adventure, Comedy, Drama
The adventures of Gustave H, a legendary concierge at a famous hotel from the fictional Republic of Zubrowka between the first and second World Wars, and Zero Moustafa, the lobby boy who becomes his most trusted friend.
2. Arrested Development (2003– )
TV-PG | 22 min | Comedy
Level-headed son Michael Bluth takes over family affairs after his father is imprisoned. But the rest of his spoiled, dysfunctional family are making his job unbearable.
4. The Curious Case of Benjamin Button (2008)
PG-13 | 166 min | Drama, Fantasy, Romance
Tells the story of Benjamin Button, a man who starts aging backwards with bizarre consequences.
6. Don Jon (2013)
R | 90 min | Comedy, Drama, Romance
A New Jersey guy dedicated to his family, friends, and church, develops unrealistic expectations from watching porn and works to find happiness and intimacy with his potential true love.
7. L.A. Confidential (1997)
R | 138 min | Crime, Drama, Mystery
As corruption grows in 1950s LA, three policemen - one strait-laced, one brutal, and one sleazy - investigate a series of murders with their own brand of justice.
8. Animal House (1978)
R | 109 min | Comedy
At a 1962 College, Dean Vernon Wormer is determined to expel the entire Delta Tau Chi Fraternity, but those trouble-makers have other plans for him.
9. The Girl Next Door (2004)
R | 108 min | Comedy, Drama, Romance
A teenager's dreams come true when a former porn star moves in next door and they fall in love.
11. 8 Mile (2002)
R | 110 min | Drama, Music
A young rapper, struggling with every aspect of his life, wants to make the most of what could be his final opportunity but his problems around gives him doubts.
12. The L Word (2004–2009)
TV-MA | 50 min | Drama, Romance
Follows the lives and loves of a small, close-knit group of lesbians living in Los Angeles as well as the friends and family members that either support or loath them.
13. The Graduate (1967)
Approved | 106 min | Comedy, Drama, Romance
A disillusioned college graduate finds himself torn between his older lover and her daughter.
14. What's Eating Gilbert Grape (1993)
PG-13 | 118 min | Drama
Gilbert has to care for his brother Arnie and his obese mother, which gets in the way when love walks into his life.
15. Wedding Crashers (2005)
R | 119 min | Comedy, Romance
John Beckwith and Jeremy Grey, a pair of committed womanizers who sneak into weddings to take advantage of the romantic tinge in the air, find themselves at odds with one another when John meets and falls for Claire Cleary.
16. That's My Boy (2012)
R | 116 min | Comedy
While in his teens, Donny fathered a son, Todd, and raised him as a single parent up until Todd's 18th birthday. Now, after not seeing each other for years, Todd's world comes crashing down when Donny resurfaces just before Todd's wedding.
17. Mamma Mia! (2008)
PG-13 | 108 min | Comedy, Musical, Romance
The story of a bride-to-be trying to find her real father told using hit songs by the popular '70s group ABBA.
18. American Wedding (2003)
R | 96 min | Comedy, Romance
It's the wedding of Jim and Michelle and the gathering of their families and friends, including Jim's old friends from high school and Michelle's little sister.
19. Behaving Badly (2014)
R | 97 min | Comedy
Teenager Rick Stevens has a crush on Nina Pennington. They form a friendship and embark on a rock n' roll journey together while Nina deals with her overbearing boyfriend, Kevin.
20. Sex and the City (2008)
R | 145 min | Comedy, Drama, Romance
A New York writer on sex and love is finally getting married to her Mr. Big. But her three best girlfriends must console her after one of them inadvertently leads Mr. Big to jilt her.
22. The Reader (2008)
R | 124 min | Drama, Romance
Post-WWII Germany: Nearly a decade after his affair with an older woman came to a mysterious end, law student Michael Berg re-encounters his former lover as she defends herself in a war-crime trial.
23. American Pie 2 (2001)
R | 108 min | Comedy, Romance
The continuing bawdy adventures of a group of friends reuniting after their first year of college.
24. Water for Elephants (2011)
PG-13 | 120 min | Drama, Romance
A veterinary student abandons his studies after his parents are killed and joins a traveling circus as their vet.
25. Grandma's Boy (2006)
R | 94 min | Comedy
A 35 year old video game tester has to move in with his grandma and her two old lady roommates.
26. You Don't Mess with the Zohan (2008)
PG-13 | 113 min | Action, Comedy
An Israeli Special Forces Soldier fakes his death so he can re-emerge in New York City as a hair stylist.
27. Enter the Void (2009)
Not Rated | 161 min | Drama, Fantasy
A U.S. drug dealer living in Tokyo is betrayed by his best friend and killed in a drug deal. His soul, observing the repercussions of his death, seeks resurrection.
29. Unfaithful (2002)
R | 124 min | Drama, Romance, Thriller
A New York suburban couple's marriage goes dangerously awry when the wife indulges in an adulterous fling.
30. Hall Pass (2011)
R | 105 min | Comedy, Romance
Rick and Fred, two husbands who are having difficulty in their marriages, are given a Hall Pass by their wives: for one week, they can do whatever they want.
31. Harold and Maude (1971)
GP | 91 min | Comedy, Romance
Young, rich, and obsessed with death, Harold finds himself changed forever when he meets lively septuagenarian Maude at a funeral.
32. Y Tu Mamá También (2001)
R | 106 min | Adventure, Comedy, Drama
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.
36. Sunset Blvd. (1950)
Not Rated | 110 min | Drama, Film-Noir
A hack screenwriter writes a screenplay for a former silent-film star who has faded into Hollywood obscurity.
37. Extract (2009)
R | 92 min | Comedy, Crime, Romance
Joel, the owner of an extract plant, tries to contend with myriad personal and professional problems, such as his potentially unfaithful wife and employees who want to take advantage of him.
38. Something's Gotta Give (2003)
PG-13 | 128 min | Comedy, Drama, Romance
A swinger on the cusp of being a senior citizen with a taste for young women falls in love with an accomplished woman closer to his age.
40. Bernie (2011)
PG-13 | 104 min | Comedy, Crime, Drama
In small-town Texas, an affable mortician strikes up a friendship with a wealthy widow, though when she starts to become controlling, he goes to great lengths to separate himself from her grasp.
42. Ken Park (2002)
Not Rated | 93 min | Drama
Ken Park is about several Californian skateboarders' lives and relationships with and without their parents.
43. All About Eve (1950)
Approved | 138 min | Drama
An ingenue insinuates herself in to the company of an established but aging stage actress and her circle of theater friends.
45. In the Land of Women (2007)
PG-13 | 97 min | Comedy, Drama, Romance
L.A. soft-porn writer Carter Webb is frustrated enough after his actress girlfriend dumps him to need a serious break. He decides to spend it with his grandmother, who can't really take ... See full summary »
46. The Producers (2005)
PG-13 | 134 min | Comedy, Musical
After putting together another Broadway flop, down-on-his-luck producer Max Bialystock teams up with timid accountant Leo Bloom in a get-rich-quick scheme to put on the world's worst show.
47. The Secret of My Succe$s (1987)
PG-13 | 111 min | Comedy
A talented young man can't get an executive position without rising through the ranks, so he comes up with a shortcut, which also benefits his love life.
48. Becoming Jane (2007)
PG | 120 min | Biography, Drama, Romance
A biographical portrait of a pre-fame Jane Austen and her romance with a young Irishman.
49. Fun Size (2012)
PG-13 | 86 min | Comedy
Wren's Halloween plans go awry when she's made to babysit her brother, who disappears into a sea of trick-or-treaters. With her best friend and two nerds at her side, she needs to find her brother before her mom finds out he's missing.
50. The Good Girl (2002)
R | 93 min | Comedy, Drama, Romance
A discount store clerk strikes up an affair with a stock boy who considers himself the incarnation of Holden Caulfield.