43 Couples Who Were Dating In 1999 That I'm Like "Wait, What?" And 14 Who Are Somehow Still Together
It's just so weird to see Freddie Prinze Jr. with someone that isn't Sarah Michelle.
First off, couples that were dating in 1999 that definitely aren't anymore:
Freddie Prinze Jr. and Kimberly McCullough:

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Ryan Reynolds and Kristen Johnston:

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Ellen DeGeneres and Anne Heche:

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Fred Durst and Carmen Electra:

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Richie Sambora and Heather Locklear:

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Sofia Coppola and Spike Jonze:

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Gwen Stefani and Gavin Rossdale:

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Susan Sarandon and Tim Robbins:

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Andre Agassi and Brooke Shields:

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Luke Wilson and Drew Barrymore:

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Ben Affleck and Gwyneth Paltrow:

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Billy Bob Thornton and Laura Dern:

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Ethan Hawke and Uma Thurman:

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Madonna and Guy Ritchie:

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Claire Danes and Ben Lee:

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Jennifer Lopez and Diddy:

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Johnathon Schaech and Christina Applegate:

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Jennifer Love Hewitt and Carson Daly:

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David Copperfield and Claudia Schiffer:

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Tom Cruise and Nicole Kidman:

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Q-Tip and Janet Jackson:

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Tommy Lee and Pamela Anderson:

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Antonio Banderas and Melanie Griffith:

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Melissa Etheridge and Julie Cypher:

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Rebecca Romijn and John Stamos:

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Eddie Furlong and Natasha Lyonne:

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David Duchovny and Tea Leoni:

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Dennis Quaid and Meg Ryan:

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Jude Law and Sadie Frost:

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Angelina Jolie and Jonny Lee Miller:

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Julia Roberts and Benjamin Bratt:

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Alec Baldwin and Kim Basinger:

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Reese Witherspoon and Ryan Phillippe:

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Mariah Cary and Luis Miguel:

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Katie Holmes and this guy:

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Elizabeth Hurley and Hugh Grant:

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Kelsey and Camille Grammer:

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Halle Berry and Eric Benet:

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Nick Lachey and Jessica Simpson:

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Sheryl Crow and Owen Wilson

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Jared Leto and Cameron Diaz:

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David Arquette and Courteney Cox:

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Ashton Kutcher and January Jones:

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And now for the couples that have been together since 1999. Truly a celeb miracle:
Elton John and David Furnish:

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Sarah Jessica Parker and Matthew Broderick:

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Danny DeVito and Rhea Perlman:

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Tom Hanks and Rita Wilson:

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Donald Trump and Melania Trump:

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Michael J. Fox and Tracy Pollan:

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Kyra Sedgwick and Kevin Bacon:

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Kurt Russel and Goldie Hawn:

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Maury Povich and Connie Chung:

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Cindy Crawford and Rande Gerber:

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Sting and Trudie Styler:

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David and Victoria Beckham:

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Will Smith and Jada Pinkett Smith:

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And Faith Hill and Tim McGraw:

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