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Movies Like Love with the Proper Stranger

If you liked Love with the Proper Stranger (1963), a comedy and drama movie directed by Robert Mulligan, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

  1. 1New York, New York

    New York, New York (1977)

    ★ 6.5/10Also romance and drama

    An egotistical saxophone player and a young singer meet on V-J Day and embark upon a strained and rocky romance, even as their careers begin a long uphill climb.

  2. 2Moonstruck

    Moonstruck (1987)

    ★ 6.8/10Also comedy and drama

    37-year-old Italian-American widow Loretta Castorini believes she is unlucky in love, and so accepts a marriage proposal from her boyfriend Johnny, even though she doesn't love him. When she meets his estranged younger…

  3. 3Funny Girl

    Funny Girl (1968)

    ★ 7.1/10Also comedy and drama

    The life of famed 1930s comedienne Fanny Brice, from her early days in the Jewish slums of New York, to the height of her career with the Ziegfeld Follies, as well as her marriage to the rakish gambler Nick Arnstein.

  4. 4High Society

    High Society (1956)

    ★ 6.8/10Also comedy and romance

    With socialite Tracy Lord about to remarry, her ex-husband - with the help of a sympathetic reporter - has 48 hours to convince her that she really still loves him.

  5. 5Is This Thing On?

    Is This Thing On? (2025)

    ★ 6.6/10Also comedy and drama

    As their marriage quietly unravels, Alex faces middle age and an impending divorce, seeking new purpose in the New York comedy scene while Tess confronts the sacrifices she made for their family—forcing them to…

  6. 6200 Cigarettes

    200 Cigarettes (1999)

    ★ 5.8/10Also comedy and drama

    In 1981 New York City, a collection of twentysomethings try to cope with relationships, loneliness, desire and their individual neuroses on New Years Eve.

  7. 7Sweet and Lowdown

    Sweet and Lowdown (1999)

    ★ 6.8/10Also comedy and drama

    In the 1930s, jazz guitarist Emmet Ray idolizes Django Reinhardt, faces gangsters and falls in love with a mute woman.

  8. 8Begin Again

    Begin Again (2014)

    ★ 7.2/10Also comedy and romance

    Gretta, a budding songwriter, finds herself alone after her boyfriend Dave ditches her. Her life gains purpose when Dan, a record label executive, notices her talent.

  9. 9Letters to Juliet

    Letters to Juliet (2010)

    ★ 7/10Also comedy and drama

    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 the "secretaries of Juliet"…

  10. 10Trust

    Trust (1990)

    ★ 6.8/10Also drama and comedy

    After being thrown away from home, pregnant high school dropout Maria meets Matthew, a highly educated and extremely moody electronics repairman. The two begin an unusual romance built on their sense of mutual…

  11. 11Quartet

    Quartet (2012)

    ★ 6.5/10Also drama and comedy

    Cissy, Reggie, and Wilf are in a home for retired musicians. Every year, there is a concert to celebrate Composer Giuseppe Verdi's birthday and they take part. Jean, who used to be married to Reggie, arrives at the…

  12. 12The Switch

    The Switch (2010)

    ★ 6.2/10Also comedy and romance

    Kassie is a smart, fun-loving single woman who, despite her neurotic best friend Wally’s objections, decides it’s time to have a baby – even if it means doing it herself… with a little help from a charming sperm donor…

  13. 135 to 7

    5 to 7 (2014)

    ★ 7.1/10Also comedy and romance

    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.

  14. 14Coyote Ugly

    Coyote Ugly (2000)

    ★ 6.3/10Also comedy and drama

    Graced with a velvet voice, 21-year-old Violet Sanford heads to New York to pursue her dream of becoming a songwriter only to find her aspirations sidelined by the accolades and notoriety she receives at her "day" job…

  15. 15Bedrooms and Hallways

    Bedrooms and Hallways (1998)

    ★ 6.1/10Also comedy and drama

    At the suggestion of a straight friend, gay man Leo joins a men’s group, where he causes some upsets by declaring his attraction to one of its members.

  16. 16The Goodbye Girl

    The Goodbye Girl (1977)

    ★ 7/10Also comedy and drama

    After being dumped by her live-in boyfriend, an unemployed dancer and her 10-year-old daughter are reluctantly forced to live with a struggling off-Broadway actor.

  17. 17Stepmom

    Stepmom (1998)

    ★ 7.2/10Also drama and romance

    Jackie is a divorced mother of two. Isabel is the career minded girlfriend of Jackie’s ex-husband Luke, forced into the role of unwelcome stepmother to their children. But when Jackie discovers she is ill, both women…

  18. 18Peace, Love & Misunderstanding

    Peace, Love & Misunderstanding (2011)

    ★ 5.8/10Also comedy and drama

    A conservative lawyer named Diane takes her two teenage children Jake and Zoe to meet their estranged, hippie grandmother in Woodstock after her husband asks for a divorce.

  19. 19The Great Gatsby

    The Great Gatsby (2013)

    ★ 7.3/10Also drama and romance

    Nick Carraway arrives in New York in 1922, an era of loose morals, glittering jazz and bootleg kings. Chasing his own American Dream, Nick encounters the mysterious millionaire Gatsby and his bewitching cousin Daisy…

  20. 20New York Stories

    New York Stories (1989)

    ★ 6.2/10Also comedy and drama

    Three tales of love, ambition, and neurosis unfold in the city that never sleeps. In "Life Lessons" (Martin Scorsese), a tormented painter channels heartbreak into his art. In "Life Without Zoë" (Francis Ford Coppola)…

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