Older Female/Younger Male Relationship
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- DirectorRobert MulliganStarsJennifer O'NeillGary GrimesJerry HouserDuring his summer vacation on Nantucket Island in 1942, a youth eagerly awaiting his first sexual encounter finds himself developing an innocent love for a young woman awaiting news on her soldier husband's fate in WWII.
- DirectorBart FreundlichStarsCatherine Zeta-JonesJustin BarthaAndrew CherryIn New York City, a single mom captivates her new neighbor, a much younger man.
- DirectorBen YoungerStarsUma ThurmanMeryl StreepBryan GreenbergA career driven professional from Manhattan is wooed by a young painter, who also happens to be the son of her psychoanalyst.
- DirectorJacob TierneyStarsLiane BalabanJay BaruchelTaylor BaruchelA Montreal high school student who believes he is the reincarnation of Lev Trotskiy starts a revolution against apathy among his fellow students.
- DirectorAlfonso CuarónStarsMaribel VerdúGael García BernalDaniel Giménez CachoIn Mexico, two teenage boys and an older woman embark on a road trip and learn a thing or two about life and each other.
- DirectorStephen DaldryStarsKate WinsletRalph FiennesBruno GanzPost-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.
- DirectorHal AshbyStarsRuth GordonBud CortVivian PicklesYoung, rich, and obsessed with death, Harold finds himself changed forever when he meets lively septuagenarian Maude at a funeral.
- DirectorKeith BeardenStarsKim CattrallDustin IngramBrian DennehyWhen an awkward teen meets his favorite porn star, whose career peaked in the '80s, an unexpected friendship follows as the young man gets a glimpse inside Monica Velour's current life as a single mom struggling to make ends meet.
- DirectorBenedek FliegaufStarsEva GreenMatt SmithLesley ManvilleA woman's consuming love forces her to bear the clone of her dead beloved. From his infancy to manhood, she faces the unavoidable complexities of her controversial decision.
- DirectorLewis John CarlinoStarsJacqueline BissetRob LoweAndrew McCarthyA young man in private school spends one crazy night out, and only later does he learn more about the woman who enlivened his night.
- DirectorGiuseppe TornatoreStarsMonica BellucciGiuseppe SulfaroLuciano FedericoAmidst the war climate, a teenage boy discovering himself becomes love-stricken by Malèna, a sensual woman living in a small, narrow-minded Italian town.
- DirectorMike NicholsStarsDustin HoffmanAnne BancroftKatharine RossA disillusioned college graduate finds himself torn between his older lover and her daughter.
- DirectorZoe R. CassavetesStarsParker PoseyMelvil PoupaudGena RowlandsSince college, Nora hasn't had much luck with men. Now in her 30s, she works in a NYC hotel going nowhere. That is, until she meets Julien.
- DirectorMilton KatselasStarsLiv UllmannEdward AlbertGene KellyForty year old Norwegian-American divorcée Ann Stanley owns her own Manhattan based real estate agency specializing in upscale Manhattan apartments. She lives with her seventeen year old daughter Trina Stanley, and her mother, Maud Ericson, who acts more the teenager than Trina. Largely because of her uptight and regimented attitude, Ann has had no love in her life since divorcing her ex-husband, character actor Billy Boylan, an irresponsible man who she still loves as a friend and who she sees whenever he is in town between acting jobs and whenever he needs money from her. Ann's uptight attitude seems to have softened slightly ever since returning from a trip to Greece with Maud. What she has not told anyone is that her softened attitude is from a romantic one night only liaison with a young American man she met by happenstance by an out of the way Greek beach, he who tried to get her to be more carefree, if only for that one night. Purely by coincidence, she meets that man again in New York. He is twenty-two year old Peter Latham, a steel heir who is an acquaintance of Trina's. While Ann's family and friends encourage her to pursue a relationship with a wealthy southern gentleman client named J.D. Rogers, Peter pursues Ann behind the scenes, while Maud believes Peter wants to court Trina. Peter is falling in love with Ann. Although she admits she is flattered by Peter's declaration, Ann may not be able to get over the difference in their ages, regardless of what she may be feeling about him. If she can let go of that repressed attitude, she may give herself the opportunity to examine if she truly does have romantic feelings for Peter, and what to do about them if they do exist. Dealing with an issue with Trina, discussing Billy's own life with him, and meeting Peter's friends and family may give Ann some insight into the matter.
- DirectorIstván SzabóStarsAnnette BeningMichael GambonMaury ChaykinSet in 1930s London, this movie involves stage actors and actresses and their experiences with love and revenge.
- DirectorPeter DouglasStarsAnn-MargretC. Thomas HowellCharles DurningA young man falls for his girlfriend's mother.
- DirectorRon SheltonStarsKevin CostnerSusan SarandonTim RobbinsA fan who has an affair with one minor-league baseball player each season meets an up-and-coming pitcher and the experienced catcher assigned to him.
- DirectorChristopher DuddyStarsJason JurmanWarren KoleJoe Mantegna2 friends graduate college and start at a law firm. Hogan is into cougars. Spence needs his employer's recommendation for Yale Law so being with his wife isn't smart. He helps Hogan start Cougar Club.
- DirectorGabriel AghionStarsCatherine DeneuveVincent LindonMathilde SeignerOn his wedding day, Antoine falls madly in love with Léa, his mother-in-law.
- DirectorPenny MarshallStarsTom HanksElizabeth PerkinsRobert LoggiaAfter wishing to be made big, a teenage boy wakes the next morning to find himself mysteriously in the body of an adult.
- DirectorBlake EdwardsStarsAudrey HepburnGeorge PeppardPatricia NealA young New York socialite becomes interested in a young man who has moved into her apartment building, but her past threatens to get in the way.
- DirectorStephen FrearsStarsMichelle PfeifferRupert FriendKathy BatesThe son of a courtesan retreats into a fantasy world after being forced to end his relationship with the older woman who educated him in the ways of love.
- DirectorScott WheelerStarsJack CullisonPhilip MarlattJoseph BootonA group of nerdy college guys who can't seem to connect with girls their own age discover the excitement of hooking up with sexy older women.
- DirectorTod WilliamsStarsJeff BridgesKim BasingerJon FosterA writer's young assistant becomes both pawn and catalyst in his boss's disintegrating household.
- DirectorJohn McKayStarsAndie MacDowellImelda StauntonAnna ChancellorThree 40-something women in a small English town meet weekly for a ritual of gin, cigarettes, and sweets -- and swap stories arguing which of them has the most pathetic love life. Kate is the headmistress at the local school; her best friends are the town's police chief and a cynical, thrice-divorced doctor. When Kate begins a fling with a handsome younger man, less worldly than her friends but passionate and sincere, the other women can't simply be happy for the couple's unusual new romance. In jealousy they promptly take it upon themselves to break up the pair, taking drastic measures which result in unintended outcomes, some happy and some tragic.