George Clooney and Karen Duffy are known to have been on at least one date when the appeared together at the Emmys on September 10, 1995. They are rumored to have had a brief romance around this time.
Daily Mail article:
STYLE: Spookily similar to George’s ex-wife Talia, this ex-model was an MTV host when they found themselves moving in the same Hollywood circles. Heavy flirtation ensued.
TIMELINE: One month.
A TRUE ROMANCE? Just a handful of dates back in 1996, but they remain good friends — she went on holiday with him last year.
SHE SAID: ‘I could never fall in love with a man with a pet pig, and George’s pig is disgusting.’
PR RATING: 9/10. She helped his lady-killer reputation begin to take hold.
Couple Profile Source