Here we've displayed a list of the best May-december Romance films : The Graduate(1967), Manhattan(1979), The Best Offer(2013), Jane Eyre(1944), Tristana(1970), Lamhe(1991), Shadowlands(1993), Middle of the Night(1959), Love in the Afternoon(1957), Venus(2006), Goodbye Again(1961), Smouldering Fires(1925) ... ...
8.0/10
Comedy, Drama
USA
1967
105 Minutes
Dustin Hoffman Anne Bancroft Katharine Ross William Daniels Murray Hamilton Elizabeth Wilson Brian Avery Walter Brooke Norman Fell Alice Ghostley Buck Henry
college graduate lawyer college student sexy woman amusing sad witty california hotel campus family home wedding may-december romance post-college aimless youth new love growing up love temptation 1960s
A disillusioned college graduate finds himself torn between his older lover and her daughter.
7.9/10
Drama, Comedy
USA
1979
96 Minutes
Woody Allen Diane Keaton Mariel Hemingway Michael Murphy Meryl Streep Anne Byrne Karen Ludwig Michael O'Donoghue Tisa Farrow Helen Hanft Bella Abzug
writer teenager ex-wife friend lover witty playful touching new york city apartment central park delicatessen dating may-december romance loneliness loss love triangle new york city growing up love
The life of a divorced television writer dating a teenage girl is further complicated when he falls in love with his best friend's mistress.
7.8/10
Drama, Romance
Italy
2013
124 Minutes
Jim Sturgess Geoffrey Rush Donald Sutherland Sylvia Hoeks Dermot Crowley Liya Kebede Philip Jackson Kiruna Stamell
auctioneer heiress art expert friend suspenseful thrilling emotional auction house villa collection women unintended consequences confinement obsession may-december romance mystery love 2010s
A lonely art expert working for a mysterious and reclusive heiress finds not only her art worth examining.
7.5/10
Drama
USA
1944
96 Minutes
Joan Fontaine Orson Welles Margaret O'Brien Peggy Ann Garner John Sutton Sara Allgood Henry Daniell Agnes Moorehead Aubrey Mather Edith Barrett Barbara Everest
governess pretty woman aristocrat housekeeper maid young girl emotional melodramatic dark england countryside estate yorkshire moors forbidden love romance may-december romance poverty class distinctions forbidden love love
After a harsh childhood, orphan Jane Eyre is hired by Edward Rochester, the brooding lord of a mysterious manor house, to care for his young daughter.
7.5/10
Drama
Spain|Italy|France
1970
98 Minutes
Catherine Deneuve Fernando Rey Franco Nero Jesus Fernandez Lola Gaos Vicente Soler
orphan nobleman artist guardian dark emotional household city toledo, spain may-december romance love exploitation illness amputation death love growing up fall revenge 1890s
Shortly after her mother's death, an innocent and youthful woman will find refuge into the household of her middle-aged aristocratic guardian, who will submit her to his sexual advances.
7.4/10
Romance
India
1991
180 Minutes
Anil Kapoor Sridevi Deepak Malhotra Waheeda Rehman Anupam Kher Dippy Sagoo
young man young woman daughter governess friend engaging emotional india london unrequited love accidental death infatuation may-december romance discovery pursuit 1990s
When the young Viren comes to India for the first time, he is captivated by Pallavi. When he learns she is already spoken for, he returns to London a broken man. When he gets the news of ... See full summary »
7.3/10
Drama
UK
1993
130 Minutes
Anthony Hopkins Debra Winger Edward Hardwicke Michael Denison Joseph Mazzello John Wood Robert Flemyng Peter Howell Peter Firth
writer poet son professor wife tender endearing sad oxford university pub england tragic death illness writers marriage may-december romance c.s. lewis discovery love transformation
C.S. Lewis, a world-renowned Christian theologian, writer and professor, leads a passionless life until he meets spirited poet Joy Gresham from the U.S.
7.2/10
Drama
USA
1959
118 Minutes
Kim Novak Fredric March Glenda Farrell Albert Van Dekker Martin Balsam Lee Grant Lee Philips Edith Meiser Joan Copeland Betty Walker Lou Gilbert
receptionist widower mother sister daughter father melodramatic gutsy factory office diner restaurant car party may-december romance divorce disapproval engagement business jealousy
A widowed businessman becomes obsessed with one of his employees, the divorcée Betty Preisser.
7.2/10
Romance
USA
1957
130 Minutes
Audrey Hepburn Gary Cooper Maurice Chevalier Van Doude John McGiver Lise Bourdin Audrey Wilder Paul Bonifas
private investigator musician millionaire playboy witty charming paris hotel train station opera house jealousy romance may-december romance lying love discovery 1950s
A middle-aged playboy becomes fascinated by the daughter of a private detective who has been hired to entrap him with the wife of a client.
7.1/10
Romance, Drama
UK
2006
95 Minutes
Peter O'Toole Leslie Phillips Jodie Whittaker Richard Griffiths Vanessa Redgrave Julian Rhind-Tutt Cathryn Bradshaw Kate Lock Corin Redgrave Liam McKenna Meg Wynn Owen
actor friend great-niece wife witty endearing london apartment museum seaside friendship troubled youth cancer death may-december romance art love pursuit 2000s
Life for a pair of veteran actors gets turned upside down after they meet a brash teenager.
7.1/10
Romance
France|USA
1961
120 Minutes
Ingrid Bergman Yves Montand Anthony Perkins Jessie Royce Landis Jackie Lane Pierre Dux Jean Clarke David Horne Lee Patrick Diahann Carroll
businessperson boyfriend mother friend cool confident paris apartment office may-december romance love triangle infidelity aging forbidden love 1960s
A successful business woman, dissatisfied with her current, philandering lover, starts an affair with a much younger man.
7.1/10
Drama
USA
1925
80 Minutes
Pauline Frederick Laura La Plante Malcolm McGregor Tully Marshall Wanda Hawley Helen Lynch George Cooper
manager secretary sister friend committee member newlywed engaging moving office factory apartment park ambition marriage of convenience rumors sister relationship self-sacrifice may-december romance quest sacrifice
A successful businesswoman falls in love with one of her (much younger) factory workers. She doesn't know that he is in love with her younger sister.
7.0/10
Drama
UK
1980
123 Minutes
Art Garfunkel Theresa Russell Harvey Keitel Denholm Elliott Daniel Massey Dana Gillespie William Hootkins Ania Marson
husband wife psychiatrist doctor police detective bleak intense uneasy hospital police station bedroom vienna party jealousy alcohol adultery sex suicide attempt may-december romance temptation
A psychiatrist, living in Vienna, enters a torrid relationship with a married woman. When she ends up in the hospital from an overdose, an inspector becomes set on discovering the demise of their affair.
7.0/10
Drama
USA
1973
108 Minutes
William Holden Kay Lenz Roger C. Carmel Marj Dusay Joan Hotchkis Jamie Smith Jackson Norman Bartold Lynn Borden Shelley Morrison Dennis Olivieri Eugene Peterson
real estate agent hippie neighbor dog lighthearted emotional uneasy los angeles house beach may-december romance culture clash peer pressure forbidden love transformation 1970s
A young girl tries to find her way in life, suffering from her own naivety and sincerity.
6.9/10
Comedy
UK|Canada
1997
93 Minutes
John Hurt Jason Priestley Fiona Loewi Sheila Hancock Maury Chaykin Gawn Grainger Elizabeth Quinn
author actor girlfriend touching charming england movie theater long island, n.y. mansion infatuation class distinctions may-december romance homosexuality transformation love 1990s
Giles De'Ath (Sir John Hurt) is a widower who doesn't like anything modern. He goes to movies and falls in love with movie star Ronnie Bostock (Jason Priestly). He then investigates ... See full summary »
6.9/10
Comedy
USA
1953
95 Minutes
Marilyn Monroe Lauren Bacall Betty Grable David Wayne Cameron Mitchell William Powell Rory Calhoun Alex D'Arcy Fred Clark
model millionaire businessman widower fortune hunter amusing charming playful new york city apartment romance wealth wedding may-december romance love quest 1950s
Three women set out to find eligible millionaires to marry, but find true love in the process.
6.9/10
Biography, Drama
UK
1972
100 Minutes
Dorothy Tutin Scott Antony Helen Mirren Lindsay Kemp Michael Gough John Justin Aubrey Richards Peter Vaughan
sculptor governess writer suffragette muse creative fascinating inspiring melodramatic paris london artist's studio art artistic struggle henri gaudier may-december romance world war i sculpting rise transformation
Biographical movie of the life of French sculptor Henri Gaudier-Brzeska (Scott Antony).
6.8/10
Comedy
USA
1941
101 Minutes
Lewis Stone Mickey Rooney Kathryn Grayson Fay Holden Ann Rutherford Sara Haden Ian Hunter Gene Reynolds
teen boy girlfriend secretary mother father lighthearted witty high school family home small town midwest may-december romance first love graduation final exams teen angst love quest growing up 1940s
Andy Hardy is about to graduate from high school and thinks he's pretty big stuff, so he hires a secretary, Kathryn Land. Kathryn and Polly Benedict, Andy's girlfriend, help him pass his ... See full summary »
6.7/10
Romance, Drama
USA
2008
111 Minutes
Penélope Cruz Ben Kingsley Dennis Hopper Peter Sarsgaard Patricia Clarkson Deborah Harry Antonio Cupo
professor student poet son best friend passionate somber new york city college may-december romance commitment student-teacher relationship father/son relationship love temptation 2000s
Cultural critic David Kepesh finds his life, which he indicates is a state of "emancipated manhood", thrown into tragic disarray by Consuela Castillo, a well-mannered student who awakens a sense of sexual possessiveness in her teacher.
6.7/10
Comedy
USA
1953
99 Minutes
William Holden David Niven Maggie McNamara Tom Tully Dawn Addams Fortunio Bonanova Gregory Ratoff Hardy Kruger Johanna Matz
young woman playboy girlfriend father lighthearted cheeky charming new york city apartment store window ledge bedroom battle of sexes virginity father/son relationship may-december romance false accusations quest temptation 1950s
Two aging playboys are both after the same attractive young woman, but she fends them off by claiming that she plans to remain a virgin until her wedding night. Both men determine to find a way around her objections.
6.7/10
Musical, Romance
USA
1955
126 Minutes
Fred Astaire Leslie Caron Terry Moore Thelma Ritter Fred Clark Charlotte Austin Larry Keating Kathryn Givney Kelly Brown Sara Shane Numa Lapeyre
millionaire orphan secretary lighthearted cheery winsome france paris new york city boarding school wealth may-december romance secret philanthropy discovery love 1950s
A wealthy American has a chance encounter with a joyful young French woman, and anonymously pays for her education. She writes letters to her mysterious benefactor, nicknaming him from the description given by some of her fellow orphans.
6.6/10
Comedy
USA
1954
98 Minutes
Dick Powell Debbie Reynolds Anne Francis Alvy Moore Glenda Farrell Horace MacMahon Herb Vigran Les Tremayne Mara Lane Maidie Norman Rita Johnson
writer juvenile delinquent best friend secretary girlfriend attorney cheeky amusing playful passionate los angeles las vegas cabin backwoods coffee shop bedroom may-december romance writing romantic dilemma living together
A Hollywood screenwriter takes in a runaway girl who's more woman than he can handle.
6.6/10
Drama
USA
1978
109 Minutes
Brooke Shields Keith Carradine Susan Sarandon Frances Faye Antonio Fargas Gerrit Graham Mae Mercer Diana Scarwid Barbara Steele Matthew Anton Seret Scott
prostitute photographer daughter madam husband melodramatic moving shocking new orleans brothel st. louis red-light district prostitution mother/daughter relationship loss of innocence virginity may-december romance sex forbidden love growing up
A teenage girl lives as a prostitute in New Orleans in 1917.
6.5/10
Musical
USA
1948
119 Minutes
Mickey Rooney Tom Drake June Allyson Perry Como Ann Sothern Betty Garrett Janet Leigh Marshall Thompson Jeanette Nolan Richard Quine Clinton Sundberg
lyricist composer actress singer best friend touching melodramatic hollywood, calif. broadway theater london new york city may-december romance alcohol songwriting friendship depression success rise fall love
Fictionalized story of the songwriting partnership of Richard Rodgers and Lorenz Hart.
6.5/10
Romance
USA
1990
103 Minutes
Susan Sarandon James Spader Jason Alexander Kathy Bates Eileen Brennan Steven Hill Rachel Levin Corey Parker Renee Taylor Jonathan Penner Barbara Howard
ad executive waitress widower friend love interest associate amusing sultry tender st. louis diner dinner party new york city bar class distinctions secret tragic death may-december romance jewish identity sex
Lust turns to love for a 40-ish working-class woman and a 20-ish yuppie adman with little in common.
6.4/10
Drama
Israel
1972
77 Minutes
Michal Bat-Adam Gabi Oterman Joseph Shiloach Levana Finkelstein Avner Hizkiyahu Moshe Tal Zivi Avramson Naomi Bachar Yehuda Efroni Esther Grotes Elisheva Michaeli
young boy brother sister-in-law grandmother rabbi love interest mellow charming powerful emotional jerusalem family home temple israel love triangle religious beliefs marriage innocence may-december romance family
The love of Nissim for his widowed sister-in-law, Rosa, in the Old City of Jerusalem at the turn of the century. Under a (very old) Jewish religious law, Nissim has the duty to marry his childless sister-in-law on the death of his brother.
6.4/10
Romance
USA
1960
100 Minutes
Clark Gable Sophia Loren Vittorio De Sica Marietto Paolo Carlini Claudio Ermelli Giovanni Filidoro
lawyer sister-in-law nephew brother italian american charming melodramatic heartwarming amusing naples, italy island family home village office capri reunion funeral custody battle may-december romance
Days before his wedding, a Philadelphia lawyer travels to Naples in Southern Italy to settle the estate of his late brother, only to find that he has an Italian nephew who is being cared for by his maternal aunt, a cabaret singer.
6.3/10
Comedy, Drama
France
1999
105 Minutes
Nathalie Baye Bulle Ogier Jacques Bonnaffé Mathilde Seigner Audrey Tautou Robert Hossein Édith Scob Marie Rivière Hélène Fillières Micheline Presle Emmanuelle Riva
beautician love interest coworker widower business owner witty charming paris beauty salon train station new love may-december romance relationships romance aging love transformation 1990s
Employees of a beauty parlor in search of love and happiness.
6.3/10
Romance
USA
1935
77 Minutes
Sylvia Sidney Herbert Marshall Philip Reed Holmes Herbert Catherine Doucet Astrid Allwyn
playwright secretary fiancée actor boss love interest playful lighthearted office apartment theater stage california beach may-december romance plays life imitating art jealousy misunderstanding marriage
A young secretary falls in love with her boss, a middle-aged playwright. Complications ensue when her boss' son falls for her.
6.3/10
Horror
USA
1981
115 Minutes
Albert Finney Diane Venora Gregory Hines Edward James Olmos Tom Noonan Dick O'Neill
detective criminologist native american creature coroner mayor gory eerie tense new york city park crime scene murder lycanthropy myth shapeshifting investigation may-december romance metamorphosis mystery
A New York cop investigates a series of brutal deaths that resemble animal attacks.
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