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Singles, Dating & Romance - Coupling-Up Movies Defined by their Era

the dating and mating relationship game
by mswoc • Created 11 years ago • Modified 9 years ago
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  • 29 titles
  • Tony Danza, Paul Michael Glaser, Christine Lahti, Mare Winningham, and Shelley Hack in Single Bars, Single Women (1984)

    1. Single Bars, Single Women

    19841h 40mTV Movie
    5.9 (113)
    The story of shallow young people who gather at singles bars looking for action. In this film, they often find it.
    DirectorHarry WinerStarsTony DanzaPaul Michael GlaserKeith Gordon
  • Classified Love (1986)

    2. Classified Love

    19861h 40mTV Movie
    6.4 (104)
    Three ad agency buddies, who cannot seem to find fulfilling love, decide to place personal ads to find new romance. The resulting blind dates and ultimate results are about what one would expect.
    DirectorDon TaylorStarsMichael McKeanStephanie FaracyDinah Manoff
  • Demi Moore, Rob Lowe, Jim Belushi, and Elizabeth Perkins in About Last Night... (1986)

    3. About Last Night...

    19861h 53m18A70Metascore
    6.3 (19K)
    Chicago singles meet in a bar, live together and call it love. Based on David Mamet's play Sexual Perversity in Chicago.
    DirectorEdward ZwickStarsRob LoweDemi MooreJim Belushi
  • Amy Irving and Peter Riegert in Crossing Delancey (1988)

    4. Crossing Delancey

    19881h 37mPG73Metascore
    6.9 (6K)
    A Manhattan single meets a man through her Jewish grandmother's matchmaker.
    DirectorJoan Micklin SilverStarsAmy IrvingPeter RiegertReizl Bozyk
  • Meg Ryan and Billy Crystal in When Harry Met Sally... (1989)

    5. When Harry Met Sally...

    19891h 35m14A76Metascore
    7.7 (266K)
    Harry and Sally have known each other for years, and are very good friends, but they fear sex would ruin the friendship.
    DirectorRob ReinerStarsBilly CrystalMeg RyanCarrie Fisher
  • Kevin Bacon and Elizabeth Perkins in He Said, She Said (1991)

    6. He Said, She Said

    19911h 55mPG
    5.7 (7.6K)
    The tumultuous relationship between the co-hosts of a morning news segment is explored from the point of view of both the man and the woman.
    DirectorsKen KwapisMarisa SilverStarsKevin BaconElizabeth PerkinsNathan Lane
  • Eddie Murphy in Boomerang (1992)

    7. Boomerang

    19921h 57m13+45Metascore
    5.6 (33K)
    A successful executive and womanizer finds his lifestyle choices have turned back on him when his new female boss turns out to be an even bigger deviant than he is.
    DirectorReginald HudlinStarsEddie MurphyRobin GivensHalle Berry
  • Matt Dillon, Bridget Fonda, Campbell Scott, and Kyra Sedgwick in Singles (1992)

    8. Singles

    19921h 39mPG71Metascore
    6.8 (35K)
    A group of young adults in their twenties, who share an apartment in the city of Seattle, ponder on love and face all the challenges of adulthood.
    DirectorCameron CroweStarsBridget FondaCampbell ScottKyra Sedgwick
  • Ethan Hawke, Winona Ryder, and Ben Stiller in Reality Bites (1994)

    9. Reality Bites

    19941h 39mPG67Metascore
    6.6 (57K)
    A documentary filmmaker and her fellow Generation X graduates face life after college, looking for work and love in Houston.
    DirectorBen StillerStarsWinona RyderEthan HawkeJaneane Garofalo
  • Waiting to Exhale (1995)

    10. Waiting to Exhale

    19952h 4m14A
    6.0 (13K)
    Follows four very different African-American women and their relationships with men.
    DirectorForest WhitakerStarsWhitney HoustonAngela BassettLoretta Devine
  • Nia Long, Larenz Tate, and Isaiah Washington in Love Jones (1997)

    11. Love Jones

    19971h 49m14A65Metascore
    7.3 (6.2K)
    A poet and photographer in Chicago explore their growing relationship while discussing love with friends. When she tests his feelings, romantic complications follow.
    DirectorTheodore WitcherStarsLarenz TateNia LongIsaiah Washington
  • How to Be a Player (1997)

    12. How to Be a Player

    19971h 33mR
    5.3 (9.5K)
    A playboy gets the tables turned on him when a party is arranged with all of the women he has been two-timing are in attendance.
    DirectorLionel C. MartinStarsBill BellamyNatalie Desselle ReidLark Voorhies
  • Robert Downey Jr., Heather Graham, and Natasha Gregson Wagner in Two Girls and a Guy (1997)

    13. Two Girls and a Guy

    19971h 24m14A66Metascore
    5.5 (8.9K)
    Two girls wait outside a young actor's door and find out he's had them both as "only" girlfriend the last ten months. They wait inside after breaking in. When Blake comes home he just can't stop lying but they stay.
    DirectorJames TobackStarsRobert Downey Jr.Heather GrahamNatasha Gregson Wagner
  • Cameron Diaz in There's Something About Mary (1998)

    14. There's Something About Mary

    19981h 59m14A69Metascore
    7.1 (345K)
    A man gets a chance to meet up with his dream girl from high school, even though his date with her back then was a complete disaster.
    DirectorsBobby FarrellyPeter FarrellyStarsCameron DiazMatt DillonBen Stiller
  • Renée Zellweger and Chris O'Donnell in The Bachelor (1999)

    15. The Bachelor

    19991h 41m14A31Metascore
    5.1 (19K)
    A commitment-phobic man goes in search of a bride, including his fed-up girlfriend, to inherit his grandfather's one hundred million dollar inheritance.
    DirectorGary SinyorStarsChris O'DonnellRenée ZellwegerArtie Lange
  • The Brothers (2001)

    16. The Brothers

    20011h 46mR50Metascore
    6.3 (5.3K)
    Four friends begin to question women and relationships when one of them announces impending nuptials.
    DirectorGary HardwickStarsMorris ChestnutShemar MooreD.L. Hughley
  • Ashley Judd in Someone Like You (2001)

    17. Someone Like You

    20011h 37mPG-1332Metascore
    6.1 (29K)
    After being jilted by her boyfriend, a talk show talent scout writes a column on the relationship habits of men which gains her national fame.
    DirectorTony GoldwynStarsAshley JuddGreg KinnearHugh Jackman
  • Vivica A. Fox, Morris Chestnut, and Anthony Anderson in Two Can Play That Game (2001)

    18. Two Can Play That Game

    20011h 30m14A35Metascore
    6.1 (7.9K)
    An arrogant career woman plays a series of heartless mind-games with her boyfriend to "put him in line," only to discover that he has a few tricks up his own sleeve.
    DirectorMark BrownStarsVivica A. FoxMorris ChestnutAnthony Anderson
  • 30 Years to Life (2001)

    19. 30 Years to Life

    20011h 50mR56Metascore
    5.9 (305)
    A group of friends each face an emotional crisis as they approach thirty years of age.
    DirectorVanessa MiddletonStarsErika AlexanderMelissa De SousaTracy Morgan
  • Taye Diggs and Sanaa Lathan in Brown Sugar (2002)

    20. Brown Sugar

    20021h 49mPG58Metascore
    6.5 (11K)
    Friends since childhood, a magazine editor and a hip-hop record executive stumble into romantic territory.
    DirectorRick FamuyiwaStarsTaye DiggsSanaa LathanYasiin Bey
  • Matthew McConaughey and Kate Hudson in How to Lose a Guy in 10 Days (2003)

    21. How to Lose a Guy in 10 Days

    20031h 56mPG45Metascore
    6.5 (311K)
    An advertising executive and ladies' man, to win a big campaign, bets that he can make a woman fall in love with him in 10 days.
    DirectorDonald PetrieStarsKate HudsonMatthew McConaugheyAdam Goldberg
  • Charisma Carpenter in See Jane Date (2003)

    22. See Jane Date

    20031h 30mTV-PGTV Movie
    5.7 (1.9K)
    A single girl living in New York tries to impress her high school nemesis by inventing the perfect boyfriend as her date to an impending wedding, then embarks on a string of blind dates to fill the bill.
    DirectorRobert BerlingerStarsCharisma CarpenterHolly Marie CombsDavid Lipper
  • Jamie Foxx in Breakin' All the Rules (2004)

    23. Breakin' All the Rules

    20041h 25mPG46Metascore
    5.6 (6.6K)
    Inspired by his fiancée (who dumped him), a man publishes a break-up hand-book for men, becoming a best-selling author in the process.
    DirectorDaniel TaplitzStarsJamie FoxxGabrielle UnionMorris Chestnut
  • Jennifer Aniston, Drew Barrymore, Jennifer Connelly, Ben Affleck, Kevin Connolly, Bradley Cooper, Ginnifer Goodwin, Scarlett Johansson, and Justin Long in He's Just Not That Into You (2009)

    24. He's Just Not That Into You

    20092h 9mPG47Metascore
    6.4 (192K)
    This Baltimore-set movie of interconnecting story arcs deals with the challenges of reading or misreading human behavior.
    DirectorKen KwapisStarsGinnifer GoodwinJennifer AnistonJennifer Connelly
  • Katherine Heigl and Gerard Butler in The Ugly Truth (2009)

    25. The Ugly Truth

    20091h 36m14A28Metascore
    6.4 (240K)
    An uptight television producer takes control of a morning show segment on modern relationships hosted by a misogynistic man.
    DirectorRobert LuketicStarsKatherine HeiglGerard ButlerBree Turner

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