List of Films Featuring May–December Romances

This is a list of mainstream movies featuring significant 'May-December' romances.

An Affair to Remember (1957)

Alfred Stieglitz: The Eloquent Eye (2001)
American Beauty (1999)
An American Haunting (2006)
An American in Paris (1951)
An Education (2009)
Atlantic City (1980)[1]
Austin Powers in Goldmember (2002)
Autumn in New York (2000)[2]
The Ballad of Jack and Rose (2005)
Beautiful Girls (1996)
Bell, Book and Candle (1958)
Big Daddy (1999)
The Big Sleep (1946)
Black Swan (2010)
Blame it on Rio (1984)
Breezy (1973)
Bulworth (1998)
Casablanca (1942)
The Cat's Meow (2001)
Chaplin (1992)
Charade (1963)
Circle of Two (1980)
Code 46 (2003)
Crazy Heart (2009)
The Crush (1993)[1]
La Cucina (2007)
Daddy Long Legs (1955)
Damage (1992)
Der blaue Engel (1930)
Dr. T and the Women (2000)
The Edge (1997)
Election (1999)
Elegy (2008)
Fair Love
Forty Carats (1973)[3]
Fresh Horses (1988)
Frida (2002)
Funny Face (1957)
Get Smart (2008)
Ghost World (2001)
The Girl in the Cafe (2005)
Girl with a Pearl Earring (2003)
Great Balls of Fire! (1989)
Gigi (1958)
Girl with Green Eyes (1964)[1]
Goldfish Memory (2003)
As Good as It Gets (1997)[3]
The Governess (1998)
Gregory's Two Girls (1999)
Guinevere (1999)[1]
Happy Endings (2005)
To Have and Have Not (1944)[3]
Hello, Schoolgirl (2008) - 30 year old civil servant and 17 year old schoolgirl
High Society (1956)
Homo Faber (1991)
The Horse Whisperer (1998)[3]
Husbands and Wives (1992)
How to Marry a Millionaire (1953)
Ikiru (1952)
Inside Daisy Clover (1965)
Interview with the Vampire (1994)[4]
Irresistible (2006)
Jane Eyre (1944)
The January Man (1989)
Kandukondain Kandukondain (2000)
Knickerbocker Holiday (1944)
Kurukkante Kalyanam (1982)
L.A. Story (1991)
Last Chance Harvey (2008)
Last Tango in Paris (1972)[4]
The Last Time (2006)
Léon (1994)
Limelight (1952)
Lisa (1989)
Little Women (1994)
Lolita (1962)[4]
Lost in Translation (2003)[4]
Love in the Afternoon (1957)[4]
Manhattan (1979)[5]
Me Without You (2001)
A Midsummer Night's Sex Comedy (1982)
Mighty Aphrodite (1995)
Mini's First Time (2006)
The Misfits (1961)
Murphy's Romance (1985)
My First Mister (2001)
Network (1976)
North by Northwest (1959)
Oldboy (2003)
The Opposite of Sex (1998)
Pale Rider (1985)
Palindromes (2004)
Paris, Texas (1984)
A Perfect Murder (1998)[3]
Petulia (1968)
Pineapple Express (2008)
Poison Ivy (1992)
Pretty Baby (1978)
Pretty Woman (1990)
The Quiet American (1958)
The Quiet American (2002)
Raja (2003)
Rio Bravo (1959)
Sabrina (1954)[3]
Sabrina (1995)
Secretary (2001)
Shopgirl (2005)[6]
Sin City (2005)[7][8]
Six Days Seven Nights (1998)[3]
Smart People (2008)
Something's Gotta Give (2003)[4]
This Is My Father (1998)
The Sound of Music (1965)
South Pacific (1958)
Stardom (2000)
Starting Out in the Evening (2007)
Stealing Beauty (1996)
Suburban Girl (2008)
Susan Slept Here (1954)
It Started in Naples (1970)[3]
Taxi Driver (1976)
Times Square (1980)
Towelhead (2007)
Twinky (1969)
Under Solen (1998)
Watchmen (2009)
Whatever Works (2009)
Wish You Were Here (1987)
Wonder Boys (2000)
True Grit (2010)
Shanghai Kiss (2007)

Older Woman/Younger Man Movies 

40 Carats (1973)
A Tiger's Tale (1987)
Ali: Fear Eats the Soul (1974
All That Heaven Allows
American Pie film series
Being Julia (2004)
Belle maman (Beautiful Mother) (1998)
Big (1988)
Breakfast at Tiffany's (1961) (Character Paul "Fred" Varjak's relationship with an older "matron" figure.)
Bull Durham (1988)
Cheri (2009)
Class (1983)
Cougar Club (2007)
Crush (2001)
Diva (1981)
The Door in the Floor (2004)
The Private Lives of Elizabeth and Essex (1939)
Sunset Boulevard (1950)
Far from Heaven (2002) [4]
The Good Girl (2002)
Goodbye Again (1961)
The Graduate (1967)[4]
Harold and Maude (1971)[4]
Hello Schoolgirl (2008)
Heading South (2005)
How Stella Got Her Groove Back (1998)[4]
I Could Never Be Your Woman (2007)
Impromptu (1992)
In Praise of Older Women (1978)
In the Bedroom (2001)
Life as a House (2001)
Losin' It (1983)
The Love Letter (1999)[1]
Lovely & Amazing (2001)
Meeting Venus (1991)
The Mother (2003)[1]
A Night in Heaven (1983)
Notes on a Scandal (2006)
P.S. (2005)[9]
The Pallbearer (1996)
Prime (2005)
Private Lessons (1981)
The Rebound (2009)
The Reader (2008)
Reckless (1997)
Rushmore (1998)
Sanky Panky (2007)
Something's Gotta Give (2003)
Summer of '42 (1971)
Tazza: The High Rollers (2006)
Tadpole (2002)
Tim (1979)[4]
White Palace (1990)
Unfaithful (2002)
Y tu mamá también (2001)

Older Man/Younger Man Movies

Chris & Don (2008)
Food of Love (2002)
L.I.E. (2001)
Love and Death on Long Island (1997)
Love Is the Devil: Study for a Portrait of Francis Bacon (1998)
Milk (2008)
The Opposite of Sex (1998)
Sugar (2004)
Sunday Bloody Sunday (1971)
Total Eclipse (1995)
Victim (1961)
Wilde (1997)

Older Woman/Younger Woman Movies

Desert Hearts (1985)
I've Heard the Mermaids Singing (1987)
High Art (1998)
Loving Annabelle (2006)
Notes on a Scandal (2006)
Bilitis (1977)