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    52 Couples Who Were Dating In 1998 That I'm Like "Wait, What?" And 17 Who Are Somehow Still Together

    I will never get over the fact that both Sarah Michelle Gellar and Freddie Prinze Jr. ever dated anyone else but each other.

    Let's start with couples who were dating in 1998 that definitely aren't together anymore...

    Freddie Prinze Jr. and Kimberly McCullough

    at shakespeare in love premiere
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Sarah Michelle Gellar and Jerry O'Connell

    at the emmys
    Nbc / NBCU Photo Bank/NBCUniversal via Getty Images

    Nicole Kidman and Tom Cruise

    at a tom cruise event
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Hugh Grant and Elizabeth Hurley

    in vegas
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Uma Thurman and Ethan Hawke

    in happier times
    Gene Shaw / Getty Images

    Charlize Theron and Stephan Jenkins

    in LA
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Kimora Lee and Russell Simmons

    on a red carpet
    Ron Galella, Ltd. / Ron Galella Collection via Getty Images

    Rebecca Romijn and John Stamos

    they are both wearing pink
    Kmazur / WireImage / Getty Images

    Ashton Kutcher and January Jones

    laughing away their pain
    New York Daily News Archive / NY Daily News via Getty Images

    Cameron Diaz and Matt Dillon

    at a vanity fair party
    Jeff Kravitz / FilmMagic / Getty Images

    Whoopi Goldberg and Frank Langella

    wearing sunglasses
    Ron Galella, Ltd. / Ron Galella Collection via Getty Images

    Mariah Carey and Derek Jeter

    mimi is smiling
    Stan Honda / AFP via Getty Images

    She's at a Yankees game in this picture.

    Matt Damon and Winona Ryder

    leaving a hotel
    Jim Smeal / Ron Galella Collection via Getty Images

    Julia Roberts and Benjamin Bratt

    at the premiere of stepmom
    Kevin.mazur / WireImage / Getty Images

    Joaquin Phoenix and Liv Tyler

    wearing plain 90s clothes
    Ron Galella / Ron Galella Collection via Getty Images

    Matt Damon and Minnie Driver

    he's hugging her and ben affleck is next to him
    Kevin.mazur / WireImage / Getty Images

    Brad Pitt and Jennifer Aniston

    he has the most 90s sunglasses on
    Barry King / WireImage / Getty Images

    Reese Witherspoon and Ryan Phillippe

    at the premiere of pleasentville
    Denny Keeler / Getty Images

    David Arquette and Courteney Cox

    at the premiere of snake eyes
    Denny Keeler / Getty Images

    Bill and Melinda Gates

    in formal attire
    Victor Malafronte / Getty Images

    David Duchovny and Téa Leoni

    at the x files premiere
    Jeff Kravitz / FilmMagic / Getty Images

    Patrick Stewart and Wendy Neuss

    at the emmys
    Nbc / NBCU Photo Bank/NBCUniversal via Getty Images

    Conan O'Brien and Lynn Kaplan

    at the golden globes
    Nbc / NBCU Photo Bank/NBCUniversal via Getty Images

    Rose McGowan and Marilyn Manson

    at a book launch
    Catherine Mcgann / Getty Images

    Ben Affleck and Gwyneth Paltrow

    leaving an airport
    Michael Ochs Archives / Getty Images

    Dylan McDermott and Shiva Rose

    at an ALS fundraiser
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Drew Barrymore and Luke Wilson

    at the ever after premiere
    Michael Ochs Archives / Getty Images

    Alec Baldwin and Kim Basinger

    at the academy awards
    Kmazur / WireImage / Getty Images

    Natasha Lyonne and Ed Furlong

    at an award show in vegas
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Kate Winslet and Jim Threapleton

    at the academy awards
    Jeff Kravitz / FilmMagic / Getty Images

    Claudia Schiffer and David Copperfield

    at the academy awards
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Carson Daly and Jennifer Love Hewitt

    she's in pink he's in a suit
    Steve.granitz / WireImage / Getty Images

    Chris Rock and Malaak Compton-Rock

    sitting
    Kmazur / WireImage / Getty Images

    Helen Hunt and Hank Azaria

    at the academy awrds
    Steve Granitz / WireImage / Getty Images

    Fiona Apple and Paul Thomas Anderson

    at the academy awards
    Steve Granitz / WireImage / Getty Images

    Jack Nicholson and Rebecca Broussard

    at the academy awards
    Steve Granitz / WireImage / Getty Images

    Ellen DeGeneres and Anne Heche

    at the golden globes
    Steve Granitz / WireImage / Getty Images

    Arnold Schwarzenegger and Maria Shriver

    at the out of sight premiere
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Mike Myers and Robin Ruzan

    at the academy awards
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Patricia Arquette and Nicolas Cage

    at a charity event
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Macaulay Culkin and Rachel Miner

    at the mighty premiere
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Lisa Loeb and Dweezil Zappa

    at a movie premiere
    Jeff Kravitz / FilmMagic / Getty Images

    Dennis Quaid and Meg Ryan

    at a movie premiere
    Jeff Kravitz / FilmMagic / Getty Images

    Kelsey Grammer and Camille Grammer-Meyer

    at a movie premiere
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    George Clooney and Céline Balitran

    at the out of sight premiere
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Vanna White and George Santo Pietro

    at carousel of hope
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Christina Applegate and Johnathon Schaech

    at the beloved premiere
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Jim Carrey and Lauren Holly

    at a charity event
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Tim Allen and Laura Deibel

    at the beloved premiere
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Garth Brooks and Sandy Mahl

    He's embracing her
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Melanie Griffith and Antonio Banderas

    at a charity event
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Rhea Perlman and Danny DeVito

    at a hotel
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    And now for the couples that are still together, over 23 years later...

    Sylvester Stallone and Jennifer Flavin

    at a charity event
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Samuel L. Jackson and LaTanya Richardson

    at the academy awards
    Steve Granitz / WireImage / Getty Images

    Goldie Hawn and Kurt Russell

    at a literal ball
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Julianne Moore and Bart Freundlich

    at the academy awards
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Michael J. Fox and Tracy Pollan

    at a movie premiere
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Ted Danson and Mary Steenburgen

    at the prince of egypt premiere
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Tom Hanks and Rita Wilson

    at the saving private ryan premiere
    Jeff Kravitz / FilmMagic, Inc / Getty images

    Sting and Trudie

    in nyc
    Victor Malafronte / Getty Images

    Will and Jada Pinkett Smith

    smiling drinking wine
    Kmazur / WireImage / Getty Images

    Jason Alexander and Daena E. Title

    at the emmys
    Nbc / NBCU Photo Bank/NBCUniversal via Getty Images

    Lisa Kudrow and Michel Stern

    at the emmys
    Nbc / NBCU Photo Bank/NBCUniversal via Getty Images

    Jay and Mavis Leno

    at the emmys
    Nbc / NBCU Photo Bank/NBCUniversal via Getty Images

    Rande Gerber and Cindy Crawford

    at the out of sight premiere
    Jeff Kravitz / FilmMagic, Inc / Getty Images

    Pierce Brosnan and Keely Shaye Smith

    at a red carpet
    Steve Granitz / WireImage / Getty Images

    Faith Hill and Tim McGraw

    sitting at an award show
    Kmazur / WireImage / Getty Images

    Angela Bassett and Courtney B. Vance

    at the premiere of how stella got her groove back
    Michael Ochs Archives / Getty Images

    And last but not least, Elton John and David Furnish

    wearing black
    Kmazur / WireImage / Getty Images

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