Best films on age gap friendships & May-December romances (older/younger lover)

This is a list of films dealing with a connection between two people who significantly differ in age, whether it's romantic love or any other kind of affection.
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1.
Léon: The Professional (1994)
    1 2 3 4 5 6 7 8 9 10 8.6/10 X  
Mathilda, a 12-year-old girl, is reluctantly taken in by Léon, a professional assassin, after her family is murdered. Léon and Mathilda form an unusual relationship, as she becomes his protégée and learns the assassin's trade. (110 mins.)
Director: Luc Besson
 
2.
Lawn Dogs (1997)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
Newly arrived in an up-market housing development, quiet ten-year-old Devon doesn't quite fit in. Ignoring the urgings of her social-climbing father... (101 mins.)
Director: John Duigan
“ Friendship ” - dunyadoom
 
3.
Towelhead (2007)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
A young Arab-American girl struggles with her sexual obsession, a bigoted Army reservist and her strict father during the Gulf War. (124 mins.)
Director: Alan Ball
 
4.
Fish Tank (2009)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
Everything changes for 15-year-old Mia when her mum brings home a new boyfriend. (123 mins.)
Director: Andrea Arnold
 
5.
The Ballad of Jack and Rose (2005)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
A father and daughter isolated on an island off the East Coast and living on a once thriving commune grapple with the limits of family and sexuality. (112 mins.)
Director: Rebecca Miller
 
6.
Notes on a Scandal (2006)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
A veteran high school teacher befriends a younger art teacher, who is having an affair with one of her 15-year-old students. However, her intentions with this new "friend" also go well beyond platonic friendship. (92 mins.)
Director: Richard Eyre
 
7.
The Piano Teacher (2001)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
A young man romantically pursues his masochistic piano teacher. (131 mins.)
Director: Michael Haneke
 
8.
The Vicious Kind (2009)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
A man tries to warn his brother away from the new girlfriend he brings home during Thanksgiving, but ends up becoming infatuated with her in the process. (92 mins.)
“ Protagonist and his brother's girl 13 year difference, but this doesn't show so much. ” - dunyadoom
 
9.
All Things Fair (1995)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
Malmö, Sweden during the Second World War. Stig is a 15 year old pupil on the verge of adulthood. Viola is 37 years old and his teacher... (130 mins.)
Director: Bo Widerberg
 
10.
An Education (2009)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
A coming-of-age story about a teenage girl in 1960s suburban London, and how her life changes with the arrival of a playboy nearly twice her age. (100 mins.)
Director: Lone Scherfig
 
11.
Oldboy (2003)
    1 2 3 4 5 6 7 8 9 10 8.4/10 X  
After being kidnapped and imprisoned for 15 years, Oh Dae-Su is released, only to find that he must find his captor in 5 days. (120 mins.)
Director: Chan-wook Park
 
12.
Another Earth (2011)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
On the night of the discovery of a duplicate Earth in the Solar system, an ambitious young student and an accomplished composer cross paths in a tragic accident. (92 mins.)
Director: Mike Cahill
 
13.
Maurice (1987)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
After his lover rejects him, a young man trapped by the oppressiveness of Edwardian society tries to come to terms with and accept his sexuality. (140 mins.)
Director: James Ivory
 
14.
Beau Pere (1981)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
After her mother dies, fourteen-year-old Marion falls in love with her stepfather, Remy. (123 mins.)
Director: Bertrand Blier
 
15.
Half Nelson (2006)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
An inner-city junior high school teacher with a drug habit forms an unlikely friendship with one of his students after she discovers his secret. (106 mins.)
Director: Ryan Fleck
“ Friendship ” - dunyadoom
 
16.
In My Father's Den (2004)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
A disillusioned war journalist's return home is blighted when he becomes implicated in the mysterious disappearance of a teenage girl he has befriended. (127 mins.)
Director: Brad McGann
“ Friendship ” - dunyadoom
 
17.
Fitzgerald (2002 TV Movie)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
Renowned writer F. Scott Fitzgerald is living the last months of his life with his youthful secretary, confidant, and protégé who later wrote a memoir of their time together. (96 mins.)
Director: Henry Bromell
 
18.
Tideland (2005)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
Because of the actions of her irresponsible parents, a young girl is left alone on a decrepit country estate and survives inside her fantastic imagination. (120 mins.)
Director: Terry Gilliam
 
19.
Digging to China (1997)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
10-year-old Harriet dreams of leaving her home, where she doesn't feel she's needed by her mother and sister Gwen... (98 mins.)
Director: Timothy Hutton
“ Friendship ” - dunyadoom
 
20.
Tyrannosaur (2011)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
Joseph, a man plagued by violence and a rage that is driving him to self-destruction, earns a chance of redemption that appears in the form of Hannah, a Christian charity shop worker. (92 mins.)
Director: Paddy Considine
“ Friendship protagonist-neighbour boy ” - dunyadoom
 
21.
Barfi! (2012)
    1 2 3 4 5 6 7 8 9 10 8.2/10 X  
Three young people learn that love can neither be defined nor contained by society's definition of normal and abnormal. (151 mins.)
Director: Anurag Basu
 
22.
L.I.E. (2001)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A 15-year-old Long Island boy loses everything and everyone he knows, soon becoming involved in a relationship with a much older man. (97 mins.)
Director: Michael Cuesta
 
23.
Mary and Max (2009)
    1 2 3 4 5 6 7 8 9 10 8.2/10 X  
A tale of friendship between two unlikely pen pals: Mary, a lonely, eight-year-old girl living in the suburbs of Melbourne, and Max, a forty-four-year old, severely obese man living in New York. (92 mins.)
Director: Adam Elliot
“ Friendship ” - dunyadoom
 
24.
The Lover (1992)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
In 1929 French Indochina, a French teenage girl embarks on a reckless and forbidden romance with a wealthy, older Chinese man, each knowing that knowledge of their affair will bring drastic consequences to each other. (115 mins.)
 
25.
The Beautiful Person (2008 TV Movie)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
Sixteen-year old Junie changes high school mid-year, following the death of her mother. She finds herself in the same class as her cousin Mathias... (97 mins.)
 
26.
Ali: Fear Eats the Soul (1974)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
An almost accidental romance is kindled between a German woman in her mid-sixties and a Moroccan migrant worker around twenty-five years younger. They abruptly decide to marry, appalling everyone around them. (94 mins.)
 
27.
You Are Alone (2005)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
A dark drama which takes a looks at how far its characters will go to relieve loneliness, even if only for an hour. (84 mins.)
Director: Gorman Bechard
 
28.
The Consequences of Love (2004)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
An introverted man's life changes completely when he finds himself attracted to a young bar-maid. (100 mins.)
 
29.
The Girl in the Café (2005 TV Movie)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
Lawrence, an aging, lonely civil servant falls for Gina, an enigmatic young woman. When he takes her to the G8 Summit in Reykjavik, however, their bond is tested by Lawrence's professional obligations. (94 mins.)
Director: David Yates
 
30.
The Band's Visit (2007)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
A band comprised of members of the Egyptian police force head to Israel to play at the inaugural ceremony of an Arab arts center, only to find themselves lost in the wrong town. (87 mins.)
Director: Eran Kolirin
 
31.
Down in the Valley (2005)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
Set in the present-day San Fernando Valley, the project revolves around a delusional man who believes he's a cowboy and the relationship that he starts with a rebellious young woman. (108 mins.)
Director: David Jacobson
 
32.
Ghost World (2001)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
With only the plan of moving in together after high school, two unusually devious friends seek direction in life. As a mere gag, they respond to a man's newspaper ad for a date, only to find it will greatly complicate their lives. (111 mins.)
Director: Terry Zwigoff
 
33.
Lolita (1997)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
A man marries his landlady so he can take advantage of her daughter. (137 mins.)
Director: Adrian Lyne
 
34.
Head-On (2004)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
In 'Gegen die Wand' Cahit, a 40-something male from Mersin in Turkey has removed everything Turkish from his life... (121 mins.)
Director: Fatih Akin
 
35.
A Short Film About Love (1988)
    1 2 3 4 5 6 7 8 9 10 8.3/10 X  
An innocent virgin spies on his frontal neighbor and falls in love with her, thus starts using tricks on her which he hopes will lead to them meeting. (86 mins.)
 
36.
The Fall (2006)
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  
In a hospital on the outskirts of 1920s Los Angeles, an injured stuntman begins to tell a fellow patient, a little girl with a broken arm, a fantastic story of five mythical heroes. Thanks to his fractured state of mind and her vivid imagination, the line between fiction and reality blurs as the tale advances. (117 mins.)
Director: Tarsem
“ Friendship ” - dunyadoom
 
37.
Breathe In (2013)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
When a foreign exchange student arrives in a small upstate New York town, she challenges the dynamics of her host family's relationships and alters their lives forever. (98 mins.)
Director: Drake Doremus