After his first marriage to actress Talia Balsam ended, George Clooney became one of Hollywood’s most famous bachelors. The couple tied the knot in 1989 but divorced in 1993 after just four years. Following the split, Clooney made headlines during a 1995 interview with Barbara Walters, where he famously declared he would never marry again, citing the failure of his first marriage.
During his bachelor years, Clooney kept his love life private, regularly denying rumors about relationships with Croatian model Monika Jaksic and actress Katie Holmes. While many of his co-stars were settling down, Clooney chose to stay single, maintaining his status as one of Hollywood’s most eligible bachelors.

However, his outlook on marriage changed when he met Amal Alamuddin (now Amal Clooney), a human rights lawyer. The two tied the knot in 2014, proving that even the most confirmed bachelors can change their minds when they meet the right person.