A few celebrity couples from the past to remind you how times have changed (24 Photos)

Madonna & Sean Penn

Billy Joel & Elizabeth Weber Small

Joshua Bowman & Miley Cyrus — A particularly devastating loss if you ask me

Orson Welles & Delores del Rio

Carrie Fisher & Paul Simon, 1983

George Clooney & Kelly Preston

Mandy Moore & Zach Braff, 2005

Jimi Hendrix & Devon Wilson, 1970

Bruce Jenner & Chystie Scott, 1977

Eddie Murphy & Nicole Mitchell, 1999

Jane Seymour & Michael Attenborough, 1971

Michael Douglas & Brenda Vaccaro

Anthony Kiedis & Ione Skye

Matthew Perry & Julia Roberts, 1996

Sean “Puff Daddy” Combs & Jennifer Lopez, 1999

Mandy Moore & Andy Roddick

Richard Gere & Cindy Crawford

Erin Everly & Axl Rose

Whitney Houston & Jermaine Jackson, 1984

Mariah Carey & Derek Jeter, 1997

Jean-Luc Godard & Anna Karina, 1961

Natalie Portman & Lukas Haas, 2004

Sidney Poitier and Juanita Hardy, 1959