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Movies Like Mary Jane's Not a Virgin Anymore

If you liked Mary Jane's Not a Virgin Anymore (1998), a comedy and drama movie directed by Sarah Jacobson, 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. 1Just Before I Go

    Just Before I Go (2015)

    ★ 6.4/10Also comedy and drama

    Ted Morgan has been treading water for most of his life. After his wife leaves him, Ted realizes he has nothing left to live for. Summoning the courage for one last act, Ted decides to go home and face the people he…

  2. 2The Giant Mechanical Man

    The Giant Mechanical Man (2012)

    ★ 6.5/10Also comedy and drama

    An offbeat romantic comedy about a silver-painted street performer and the soft spoken zoo worker who falls for him.

  3. 3He Said, She Said

    He Said, She Said (1991)

    ★ 5.9/10Also comedy and drama

    Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing their very different opinions…

  4. 4Numb

    Numb (2007)

    ★ 5.9/10Also comedy and drama

    Hudson Milbank is a successful Hollywood screenwriter who suddenly and strangely finds himself without any emotional feelings. He tries doctor after doctor and shrink after shrink, but nothing works. The Golf Channel…

  5. 5Fast Times at Ridgemont High

    Fast Times at Ridgemont High (1982)

    ★ 6.8/10Also comedy and romance

    A group of Southern-California high school students ignore their studies in favor of indulging in their teenage distractions.

  6. 6Delirious

    Delirious (2007)

    ★ 6.3/10Also comedy and drama

    Les, a small-time celebrity photographer desperate to make it big, befriends Toby, a homeless young man with no direction except a vague desire to become an actor. When by chance, Toby becomes romantically involved…

  7. 7Sidewalks of New York

    Sidewalks of New York (2001)

    ★ 6.1/10Also comedy and drama

    The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives…

  8. 8XX/XY

    XX/XY (2002)

    ★ 6/10Also drama and comedy

    Three friends begin a dangerous three-way relationship that spirals out of control, leading to dire consequences that haunt them ten years later.

  9. 9Love & Sex

    Love & Sex (2000)

    ★ 6.2/10Also comedy and drama

    When her rather explicit copy is rejected, magazine journalist Kate is asked by her editor to come up with an article on loving relationships instead, and to do so by the end of the day. This gets Kate thinking back…

  10. 10Is 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…

  11. 11The Big Picture

    The Big Picture (1989)

    ★ 5.9/10Also comedy and romance

    Hollywood beckons for recent film school grad Nick Chapman, who is out to capitalize on the momentum from his national award-winning student film. Studio executive Allen Habel seduces Nick with a dream deal to make his…

  12. 12How to Please a Woman

    How to Please a Woman (2022)

    ★ 6.3/10Also romance and comedy

    When her all-male house-cleaning business gets out of control, a mature woman must embrace her own sexuality, if she is to make a new life for herself.

  13. 13The Panic in Needle Park

    The Panic in Needle Park (1971)

    ★ 6.8/10Also drama and romance

    A stark portrayal of life among a group of heroin addicts who hang out in Needle Park in New York City. Played against this setting is a low-key love story between Bobby, a young addict and small-time hustler, and…

  14. 14Valley Girl

    Valley Girl (1983)

    ★ 6/10Also comedy and romance

    Julie, a girl from the valley, meets Randy, a punk from the city. They are from different worlds and find love. Somehow they need to stay together in spite of her trendy, shallow friends.

  15. 15Young People Fucking

    Young People Fucking (2007)

    ★ 5.9/10Also comedy and drama

    On a Tuesday night, five couples have separate sexual adventures. Matt and Kris, friends for years, want to have an only-once, no-strings good time. Abby and Andrew, married, celebrate his birthday, but it's marred by…

  16. 16The Wackness

    The Wackness (2008)

    ★ 6.4/10Also drama and comedy

    Set in New York City in the sweltering summer, The Wackness tells the story of a troubled teenage drug dealer, who trades pot for therapy sessions with a drug-addled psychiatrist. Things get more complicated when he…

  17. 17Peace, 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.

  18. 18Other People's Money

    Other People's Money (1991)

    ★ 6.1/10Also comedy and drama

    When a corporate raider threatens a hostile takeover of a 'mom and pop' company, the patriarch of the company enlists the help of his wife's attractive daughter—who is a lawyer—to stop the takeover. However, the raider…

  19. 19The Baltimorons

    The Baltimorons (2025)

    ★ 6.3/10Also comedy and drama

    A newly sober man's Christmas Eve dental emergency leads to an unexpected romance with his older dentist as they explore Baltimore together.

  20. 20The Life List

    The Life List (2025)

    ★ 6.9/10Also romance and comedy

    When her mother sends her on a quest to complete a teenage bucket list, a young woman uncovers family secrets, finds romance — and rediscovers herself.

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