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Celebrities That Were An Item A Long Time Ago (66 pics)

Posted in Lifestyle » Celebs   16 Aug 2016   / 6370 views

You probably don’t even remember that these celebrities were dating back in the day.
 

Adam Brody and Rachel Bilson

Rachel and Adam started dating during the first season of The O.C. and called it quits in 2006.

Cameron Diaz and Matt Dillon

Cameron and Matt, who costarred in 1998's There's Something About Mary, dated between 1995 and 1998.

Jack Nicholson and Lara Flynn Boyle

Jack had an on-and-off romance with Lara for about six years.

Josh Groban and January Jones

Josh and January dated from 2003-2006.

Salma Hayek and Edward Norton

Salma and Edward were in a relationship for multiple years in the beginning of the 2000s.

Jennifer Lopez and Diddy

After her 1998 divorce from Ojani Noa, J Lo dated Diddy for almost a year and a half.

Kristen Johnston and Ryan Reynolds

Ryan and Kristen briefly dated before Ryan's romance with Alanis Morissette.

Jennifer Esposito and Bradley Cooper

Bradley married Jennifer in 2006, and the couple divorced in 2007. Bradley then went on to date Renée Zellweger.

Emma Stone and Kieran Culkin

Emma and Kieran were rumored to be an item around 2009 and 2010.

Gwen Stefani and Tony Kanal

Gwen's breakup from bandmate Tony inspired multiple songs on No Doubt's Tragic Kingdom album.

Brooke Shields and Andre Agassi

Brooke started seeing Andre in 1993, and the duo were married from 1997 to 1999.

Kate Hudson and Alex Rodriguez

Kate paired up with Alex in 2009 after her divorce from Chris Robinson.

Sarah Jessica Parker and Robert Downey Jr.

SJP and RDJ were an item from 1984 until 1991.

Julia Roberts and Lyle Lovett

Julia and Lyle were married from 1993-1995.

Katie Holmes and Chris Klein

Katie and Chris were a pair from 2000 to 2005, during which they became engaged.

Alanis Morissette and Ryan Reynolds

Ryan became engaged to Alanis in 2004, but they split in 2007 after deciding not to walk down the aisle.

Kelly Preston and George Clooney

George and Kelly lived together while dating in 1988.

Penelope Cruz and Tom Cruise

Tom and Penelope appeared together in 2001's Vanilla Sky and fizzled out in 2004.

Lance Armstrong and Sheryl Crow

Lance and Sheryl lasted from 2003 to 2006, during which they were engaged.

Jennifer Lopez and Wesley Snipes

Jennifer and Wesley were reportedly together for a short time in 1994.

Helen Hunt and Hank Azaria

Hank and Helen were married from 1999 to 2000, but in 2001 Helen began a relationship with Matthew Carnahan.

Julia Roberts and Kiefer Sutherland

Julia and Kiefer worked on Flatliners in 1990 and announced their engagement shortly after. Julia called off the wedding just three days before the nuptials were set to take place on June 14, 1991.

Alyssa Milano and Scott Wolf

Alyssa and Scott fell in love in 1994.

Mila Kunis and Macaulay Caulkin

Mila was 18 when she started dating Macaulay. Their romance lasted eight years and ended in early 2011.

John Krasinski and Rashida Jones

John and Rashida dated before working on The Office together.

Ashley Judd and Michael Bolton

Ashley and Michael wrapped up their romance in 1997.

Heather Graham and Heath Ledger

Heath and Heather had a short relationship in 2000.

Christina Applegate and Brad Pitt

Christina and Brad got together briefly in 1988.

Megan Fox and David Gallagher

Megan cozied up to David in 2003.

Busy Philipps and Colin Hanks

Busy and Colin dated after they both attended Loyola Marymount University.

Jennifer Aniston and Tate Donovan

Jennifer and Tate were an item for almost three years before they broke up in 1998.

Courteney Cox and Michael Keaton

Courteney and Michael ended their relationship of five and a half years in 1995.

Jason Schwartzman and Zooey Deschanel

Jason and Zooey were an item until 2005.

Cher and Richie Sambora

Cher and Richie dated for about two years in the '90s.

Marla Sokoloff and James Franco

Marla and James were an item before he started dating Ahna O'Reilly in 2006.

Jennifer Love Hewitt and Joey Lawrence

Jennifer and Joey stepped out together in 1996.

Michelle Trachtenberg and Pete Wentz

Michelle and Pete got together in 2006, before he got engaged to Ashlee Simpson in 2008.

Kirsten Dunst and Jake Gyllenhaal

Kirsten and Jake were an item for almost two years before breaking up in 2002.

Demi Moore and Emilio Estevez

Demi and Emilio had a quick fling between 1986 and 1987.

Drew Barrymore and David Arquette

Drew and David linked up in 1991.

Katy Perry and Travie McCoy

Katy's romance with Travie from Gym Class Heroes ended in 2009.

Nicky Hilton and Kevin Connolly

Nicky and Kevin were a pair for two years.

Moby and Natalie Portman

Moby said of his time with Natalie, "As far as the very brief affair that I had with Natalie, it's made me a target of a lot of nerd wrath."

Tyra Banks and Seal

Heidi Klum wasn't the first model to catch Seal's eye - he also dated Tyra in 1992.

Winona Ryder and Matt Damon

Winona and Matt matched up in 1997.

Courtney Love and Edward Norton

Courtney and Edward were engaged for six months during their 1996 to 1999 relationship.

Melissa Gilbert and Rob Lowe

Rob and Melissa dated on and off from 1981 to 1987.

Jennifer Garner and Michael Vartan

After Jennifer's divorce from Scott Foley in 2003, she sparked a relationship with Alias costar Michael that lasted for about six months.

Madonna and Sean Penn

Madonna and Sean got married in 1985 but were divorced by 1989.

Whitney Houston and Ray J

Whitney matched up with a much younger Ray J in 2008.

Minka Kelly and Donald Faison

Minka dated Donald for about a year before they broke up in 2005 and she coupled up with musician John Mayer.

Hilary Duff and Joel Madden

Hilary was 16 when she started dating Joel in 2004; they broke up in 2006.

Leelee Sobieski and Sean Lennon

Leelee and Sean were a duo in 2003.

Jennifer Aniston and John Mayer

Jennifer and John debuted their love on the red carpet in February 2009, but broke up shortly after.

Tara Reid and Carson Daly

Carson and Tara broke off their engagement in 2001.

Cameron Diaz and Justin Timberlake

Justin and Cameron were an item from 2003 to 2007, when they issued a joint statement about their breakup.

Ellen Barkin and Johnny Depp

Johnny and Ellen got together in the early '90s.

January Jones and Ashton Kutcher

January and Ashton were together for about three years before breaking up in 2001.

Owen Wilson and Sheryl Crow

Sheryl released a song in 2002 titled "Safe and Sound" about her relationship with Owen.

James Franco and Ahna O'Reilly

James and Ahna spent five years together after they started dating in 2006.

Cindy Crawford and Richard Gere

Cindy and Richard were married from 1991 to 1995.

Brad Pitt and Juliette Lewis

Juliette was just 16 when she started dating Brad, who was 10 years older, in the '90s.

Sandra Bullock and Ryan Gosling

Ryan and Sandra got together between 2002 and 2003.

Gwyneth Paltrow and Brad Pitt

Brad and Gwyneth were engaged for six months but called the union off in 1997.

Wilmer Valderrama and Mandy Moore

Wilmer and Mandy got romantic from 2001 to 2002.

Angelina Jolie and Billy Bob Thornton

Angelina and Billy Bob met in 1999 while filming Pushing Tin and were married in 2000. They divorced in 2002 with Angelina taking custody of their newly adopted son, Maddox.




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