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Celebrity hookups in 1999

Hollywood cycles through hook-ups and bust-ups like there's no tomorrow. Trying to work out who is with who at any one time is sometimes challenging! See who hooked up in 1999. This list has been viewed 8,317 times.
This list has 954 members. See also Celebrity hookups by year, Celebrity events in 1999, 1999
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  • Jennifer Syme and Keanu Reeves
    Jennifer Syme and Keanu Reeves Keanu Reeves and Jennifer Syme dated from 1999 to 2000.
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    rank #1 · 2 3
  • Jamie White and Tom Welling
    Jamie White and Tom Welling Tom Welling and Jamie White were married for 13 years. They dated for 1 year after getting together in Jun 1999. After a 1 year engagement they married on 5th Jul 2002. 13 years later they separated in Dec 2012 and divorced on 22nd Nov 2015.
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    rank #2 · 32 63 43
  • Eric Clapton and Melia McEnery
    Eric Clapton and Melia McEnery Melia McEnery and Eric Clapton have been married for 19 years. They were dating for 3 years after getting together in 1999 and were married on 1st Jan 2002.
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    rank #3 · 7 34 13
  • Nick Cannon and Nicole Scherzinger
    Nick Cannon and Nicole Scherzinger Nicole Scherzinger and Nick Cannon dated from 1999 to 2000.
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    rank #4 ·
  • Jay-Z and Aaliyah
    Jay-Z and Aaliyah Aaliyah and Jay-Z dated from 1999 to July, 2000.
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    rank #5 · 23 3 2
  • Kim Kardashian and Damon Thomas
    Kim Kardashian and Damon Thomas Damon Thomas and Kim Kardashian West were married for 4 years. They dated for 4 months after getting together in Sep 1999 and married on 22nd Jan 2000. 4 years later they divorced in Feb 2004.
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    rank #6 · 1 2 1
  • Aaliyah and Damon Dash
    Aaliyah and Damon Dash Damon Dash and Aaliyah were in a relationship for 1 year before Aaliyah died aged 22.
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    rank #7 · 28 9 4
  • Mark Calaway and Sara Calaway
    Mark Calaway and Sara Calaway Sara Calaway and Mark Calaway were married for 6 years. They dated for 10 days after getting together in 1999. After a 1 year engagement they married on 21st Jul 2000. 6 years later they divorced on 25th Apr 2007.
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    rank #8 · 35 73 64
  • Omar Epps and Sanaa Lathan
    Omar Epps and Sanaa Lathan Sanaa Lathan and Omar Epps dated from 1999 to March, 2002.
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    rank #9 · 15 14 8
  • Lyle Lovett and April Kimble
    Lyle Lovett and April Kimble April Kimble and Lyle Lovett have been engaged for 18 years. They started dating in 1999 and after 4 years were engaged in 2003.
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    rank #10 · 11
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