OMG They Dated?!: Hot Mess Fashion Edition

Brooke Shields and Liam Neeson

Samaire Armstrong and Aaron Paul

Colin Hanks and Busy Phllips

Megan Fox and This Guy from your Childhood

Leann Rimes and This Guy from your Childhood

Chris Pratt and the girl from Revenge

Jennifer Love Hewitt and Patrick Wilson

Ben Foster and Kiki

Rosario Dawson and Jay Z

Rosario Dawson and Joshua Jackson

Colin Firth and Meg Tilly

Matthew McCounaughey and Ashley Judd

JRM and Toni Collette

Ben Stiller and Jeanne Tripplehorn

Brad Pitt and Robin Givens

Brad Pitt and Thandie Newton

Brad Pitt and Sinitta

Channing Tatum and Amanda Bynes

Eve and Stevie J

Rachel Leigh Cook and Shane West

Helen Hunt and Matthew Broderick

Cher and Tom Cruise

George Clooney and Kelly Preston

Halle Berry and Danny Wood

Paula Abdul and John Stamos

Josh Groban and January Jones

Kathy Griffin and Jack Black (no hot mess fashion ... but a hot mess nonetheless)

Bon Jovi and Diane Lane

Rick James and Linda Blair

Natalie Portman and Lucas Haas

Natalie Portman and Moby

Michael Sheen and Kate Beckinsale (pretty well known but Michaels outfit ...)

Quentin Tarantino and Mira Sorvino

Matthew Perry and Julia Roberts

Dylan McDermott and/or Dermot Mulroney and Julia Roberts

Christian Slater and Rosie Perez

Kangaroo Jack and Sarah Michelle Gellar

Ryan Gosling and Sandra Bullock

Shemar Moore and Halle Berry

Shemar Moore and Toni Braxton

Whoopi and Timothy Dalton (they look fine but i had no idea they were together lol)

Source: + some google searching.