They either seemed like an off-fitting pair or we have long forgotten that they were an item. These are Hollywood’s most odd couples.
Jon Cryer, 50, once romanced Demi Moore, 52. Sadly, he says his “inaugural Hollywood romance” ended when he stopped by Demi’s place one night, only to have her housekeeper reveal that she was “out with her boyfriend.”
Christina Applegate, 43, and Brad Pitt, 51, walked the red carpet together in 1989 — but never made it past the first date! “We went to the MTV Movie Awards, and I ditched him,” confesses Christina. “I left with somebody else!”
Kelly Preston, 52, and George Clooney, 53, dated for two years beginning in 1987, sharing a home in Hollywood and custody of a potbellied pig named Max, which George kept after the couple split.