#4: Clint Eastwood

While Clint Eastwood has only been married twice, the former actor and political figure has had numerous relationships and romantic encounters throughout the years. He was married to his first wife, Maggie Johnson, from 1953 to 1984 and they had two children together, Kyle and Alison.

They had an open marriage, throughout which Eastwood had different romantic affairs. He married his second wife, Dina Ruiz, in 1996, and the couple divorced in 2014; they had one daughter together, Morgan. His son Scott, who followed his father’s footsteps in the entertainment industry, was born in 1986 to Jacelyn Reeves, Eastwood’s then-girlfriend.