George Clooney & Kelly Preston – 1989
Even if dating apps were a thing back in the day, Hollywood heartthrob George Clooney wouldn’t need them because he can easily find a pretty, intelligent, and talented woman to date. He got romantically involved with actress Kelly Preston during the late ’80s, and their relationship lasted for about two years.
They lived in a house together and took care of a pig named Max. Months after breaking up in 1989, he moved on fast and married Talia Balsam. Their marriage ended in 1993, and he ultimately tied the knot with barrister Amal Alamuddin in 2014. Meanwhile, Preston passed away at the age of 57 in 2020.
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