Yup, they dated. Weird. I know. (27 photos)

Kim Kardashian & Nick Cannon

Jennifer Connelly & Josh Charles

Matthew Perry & Heather Graham

Travis Stork & Carrie Underwood

Sharon Stone & Christian Slater

Chris O’Donnell & Reese Witherspoon

Anna Paquin & Logan Marshall-Green

Jake Gyllenhaal & Minka Kelly

Ashlee Simpson & Gregory Smith

Joshua Jackson & Rosario Dawson

Kylie Minogue & Lenny Kravitz

Shemar Moore & Toni Braxton

Christian Bale & Drew Barrymore

Jordana Brewter & Mark Wahlberg

Ellen Barkin & Johnny Depp

Val Kilmer & Cher

Emma Thompson & Hugh Laurie

Kathy Griffin & Jack Black

Jewel & Sean Penn

Ashley Greene & Ian Somerhalder

Drew Barrymore & David Arquette

Topher Grace & Camilla Belle

Jessica Simpson & Billy Corgan

Jessica Biel & Derek Jeter

Eddie Murphy & Toni Braxton

Cameron Diaz & Edward Norton

Winona Ryder & David Duchovny