20 best movies like Love with the Proper Stranger (1963)

An immature, newly unemployed comic must navigate the murky waters of adulthood after her fling with a graduate student results in an unplanned pregnancy.

A mother takes her two sons on an unusual road trip from New York. Pittsburgh, St. Louis and eventually Hollywood in her quest to find a man to take care of them all.

Annie is stuck in a long-term relationship with Duncan – an obsessive fan of obscure rocker Tucker Crowe. When the acoustic demo of Tucker's hit record from 25 years ago surfaces, its discovery leads to a life-changing encounter with the elusive rocker himself.

A pregnant New York social worker begins to develop romantic feelings for her gay best friend, and decides she'd rather raise her child with him, much to the dismay of her overbearing boyfriend.

A 16-year-old girl and her extended family are left reeling after her calculating grandmother unveils an array of secrets on her deathbed.

A Jewish man and a jewish woman meet and while attracted to each other find that their worlds are very different. She is the archetypical Jewish-American-Princess, very emotionally involved with her parents world and the world they have created for her while he is much less dependent on his family. They begin an affair which brings more differences to the surface.

Revolves around a young couple and their friends struggling with adulthood and issues of relationships and commitment. Based on the 2001 Italian film L'ultimo bacio, directed by Gabriele Muccino.

Maggie's plan to have a baby on her own is derailed when she falls in love with John, a married man, destroying his volatile marriage to the brilliant and impossible Georgette. But one daughter and three years later, Maggie is out of love and in a quandary: what do you do when you suspect your man and his ex wife are actually perfect for each other?

Angie lives in the Bensonhurst section of Brooklyn, N.Y. and dreams of a better life than everyone she knows. When she finds that she is pregnant by her boyfriend Vinnie, she decides that she will have the baby, but not Vinnie as a husband. This turns the entire neighborhood upside down and starts her on a journey of self discovery. This journey includes her family, a new lover and her life. Even her best friend Tina has trouble understanding Angie. Written by Tony Fontana

Deals with the lives of the three Irish Catholic McMullen brothers from Long Island, New York, over three months, as they grapple with basic ideas and values — love, sex, marriage, religion and family — in the 1990s. Directed, written, produced by and starring Edward Burns.

Everyone deserves a great love story. But for seventeen-year old Simon Spier it's a little more complicated: he's yet to tell his family or friends he's gay and he doesn't know the identity of the anonymous classmate he's fallen for online.

Shy, straight-A student Ellie is hired by sweet but inarticulate jock Paul, who needs help wooing the most popular girl in school. But their new and unlikely friendship gets tricky when Ellie discovers she has feelings for the same girl.

It's Hollywood, 1958. Small town beauty queen and devout Baptist virgin Marla Mabrey, under contract to the infamous Howard Hughes, arrives in Los Angeles. At the airport, she meets her driver Frank Forbes, who is engaged to be married to his seventh grade sweetheart and is a deeply religious Methodist. Their instant attraction not only puts their religious convictions to the test, but also defies Hughes' number one rule: No employee is allowed to have any relationship whatsoever with a contract actress. Hughes' behavior intersects with Marla and Frank in very separate and unexpected ways, and as they are drawn deeper into his bizarre world, their values are challenged and their lives are changed.

A working girl from New Jersey looks for love with a fast-lane Manhattan salesman from Queens.

A woman at rock bottom must find her way across Los Angeles in order to crash her ex-boyfriend's engagement party.

The story of a young man who arrives in Hollywood during the 1930s hoping to work in the film industry, falls in love, and finds himself swept up in the vibrant café society that defined the spirit of the age.

A young writer begins an affair with an older woman from France whose open marriage to a diplomat dictates that they can meet only between the hours of 5 p.m. to 7 p.m.

Hours after his release from prison, Jesus Quintana pairs up with fellow misfits Petey and Marie for a freewheeling joyride of petty crime and romance.

For Tobe, a nerdy, horny, frizzy-haired cineaste who doesn't quite fit in with the average contemporary teen, the pinnacle of womanhood is Monica Velour, a soft-core actress who reached the zenith of her career in the 1980s. When Tobe learns that his love idol is headlining hundreds of miles away at the Gentlemen's Petting Zoo in Indiana, he drives off with carefree glory, filled with the hope of meeting her.

An American girl on vacation in Italy finds an unanswered "letter to Juliet" -- one of thousands of missives left at the fictional lover's Verona courtyard, which are typically answered by a the "secretaries of Juliet" -- and she goes on a quest to find the lovers referenced in the letter.

The separation of a long married couple goes awry when they fall for each other again.

A woman on the brink of a marriage proposal is told by a friend that she should date other men before spending the rest of her life with her boyfriend.

An unmarried 40-year-old woman turns to a turkey baster in order to become pregnant. Seven years later, she reunites with her best friend, who has been living with a secret: he replaced her preferred sperm sample with his own.

Mia, an aspiring actress, serves lattes to movie stars in between auditions and Sebastian, a jazz musician, scrapes by playing cocktail party gigs in dingy bars, but as success mounts they are faced with decisions that begin to fray the fragile fabric of their love affair, and the dreams they worked so hard to maintain in each other threaten to rip them apart.

During their travels from Chicago to New York, Harry and Sally Will debate whether or not sex ruins a perfect relationship between a man and a woman. Eleven years later, and they're still no closer to finding the answer.

Henry and Nicky are small town pals from blue collar families with only a short time before they ship off to World War II. Henry begins romancing new-to-town Caddie Winger, believing her to be wealthy. Mischievious and irresponsible, Nicky gets into trouble which forces the other two to become involved, testing their relationship, as well as the friendship between the boys.

A womanizing poet falls into the hands of a psychiatrist with a straying wife.

Wayne Dobie is a shy cop whose low-key demeanor has earned him the affectionate nickname "Mad Dog." After Mad Dog saves the life of Frank Milo, a crime boss and aspiring stand-up comedian, he's offered the company of an attractive young waitress named Glory for a week. At first both are uneasy about the arrangement, but they eventually fall in love. However, the situation becomes complicated when Milo demands Glory back.

One man does all he can to veil his Asian heritage; the other takes great pains to hide his sexual orientation. Both of these things begin to change when Ryan is hired to prepare film star Ning for a fashion shoot, and the men develop a bond.

Straitlaced Princeton University admissions officer, Portia Nathan is caught off-guard when she makes a recruiting visit to an alternative high school overseen by her former college classmate, the freewheeling John Pressman. Pressman has surmised that Jeremiah, his gifted yet very unconventional student, might well be the son that Portia secretly gave up for adoption many years ago.

A Hollywood-set romantic tale of a guy who is content to live his life without a job yet with the love of his life, a young actress.

Miles buys himself a state-of-the-art computer that starts expressing thoughts and emotions after a having champagne spilled down on him. Things start getting out of hand when both Miles and Edgar, how the computer calls himself, fall in love with Madeline, an attractive neighbour.

Overachieving actress, Rebecca (Moore), must come to grips with her failing marriage to stay-at-home dad, Tom (Duchovny). While Rebecca's slacker brother, Tobey (Billy Crudup), can't seem to commit to his aspiring-novelist girlfriend, Elaine (Maggie Gyllenhaal). As both relationships spin out of control, the two couples embark on a quest to rediscover the magic and romance of falling in love in New York.

In this coming-of-age comedy, Tim Dunphy is leading a go-nowhere existence, spending his days smoking pot and hanging out with his best friend, Drugs Delaney. But Tim's lazy days of getting high are jettisoned after a brush with the law convinces his blue-collar dad to send him to a Connecticut prep school. The one saving grace of the new school is Jane, a fellow student Tim falls for immediately.

Charlie Lang is a simple, kindhearted New York City cop. When he realizes he has no money to tip waitress Yvonne Biasi, Lang offers her half the winnings of his lottery ticket. Amazingly, the ticket happens to be a winner, in the sum of $4 million. True to his word, Lang proceeds to share the prize money with Biasi, which infuriates his greedy wife, Muriel. Not content with the arrangement, Muriel begins scheming to take all the money.

Fortune hunter Holly Golightly finds herself captivated by aspiring writer Paul Varjak, who's moved into her building on a wealthy woman's dime. As romance blooms between Paul and Holly, Doc Golightly shows up on the scene, revealing Holly's past.

A young girl named Juno gets herself pregnant and tries to stand on her own, but soon learns a few lessons about being grown up.

Providing the romantic comedy genre with a decidedly queer twist, THE ONE is an effortlessly charming tale which proves that love is never simple! Hunky Daniel couldn’t have it better: great parents, a successful career and his beautiful fiancée Jen. But in his seemingly perfect life, there is one temptation- he has a thing for his adorable, openly gay former college classmate Tommy. After a few drinks, Daniel succumbs to his repressed desires sending these two on a torrid affair. Funny how love and lust have a way of messing up even the best laid plans of man!

After being discharged from the Army, Brian Flanagan moves back to Queens and takes a job in a bar run by Doug Coughlin, who teaches Brian the fine art of bar-tending. Brian quickly becomes a patron favorite with his flashy drink-mixing style. Brian adopts his mentor's cynical philosophy on life and goes for the money. He leaves his artist girlfriend Jordan Mooney for Bonnie, a wealthy, high-powered executive. Brian soon must chose between the two, as he evaluates his options.

Left broke and homeless by his wealthy parents' divorce, a young man moves in with an old friend and finally meets the woman of his dreams -- only to discover she's already dating his friend.

Director Jean Renoir’s entrancing first color feature—shot entirely on location in India—is a visual tour de force. Based on the novel by Rumer Godden, the film eloquently contrasts the growing pains of three young women with the immutability of the Bengal river around which their daily lives unfold. Enriched by Renoir’s subtle understanding and appreciation for India and its people, The River gracefully explores the fragile connections between transitory emotions and everlasting creation.

Aspiring architect Tom Thompson is told by mysterious Ruth Abernathy that his best friend, "Bill," has taken his own life. Except that Tom has never met Bill and neither have his incredulous friends. So when Tom foolishly agrees to give the eulogy at Bill's funeral, it sets him on a collision course with Ruth -- who is revealed to be Bill's oversexed mother -- and Julie DeMarco, the longtime crush Tom hasn't seen since they were teens.

A woman struggles to escape the clutches of her overbearing, co-dependent mother, while gradually falling for a sexy, sophisticated attorney.

A sex therapist goes through puberty after the successful removal of a benign tumor resting against his pituitary gland. He experiences all the changes and effects of puberty over a three-week period.

As a young New York couple goes from college romance to marriage and the birth of their first child, the unexpected twists of their journey create reverberations that echo over continents and through lifetimes.

The lives of two struggling musicians, who happen to be brothers, inevitably change when they team up with a beautiful, up-and-coming singer.

In Manhattan, the British limousine driver Alfie is surrounded by beautiful women, having one night stands with all of them and without any sort of commitment. His best friends are his colleague Marlon and his girl-friend Lonette. Alfie has a brief affair with Lonette, and the consequences of his act forces Alfie to reflect over his lifestyle.

At her husband's funeral, Pearl (Shirley MacLaine), Jewish mother of two divorced and antagonistic daughters, meets an old Italian friend (Marcello Mastroianni) of her husband, whose advice years previously had stopped the husband leaving home. For 23 years he, now a widower, has secretly loved Pearl...

A New York schoolteacher hits a midlife crisis when, in quick succession, her husband leaves, her adoptive mother dies and her biological mother, an eccentric talk show host, materializes and turns her life upside down as she begins a courtship with the father of one of her students.

An unusual, real-world romance involving relatable people, with one catch - there are three of them! You Me Her infuses the sensibilities of a smart, grounded indie rom-com with a distinctive twist: one of the two parties just happens to be a suburban married couple.