Gwyneth Paltrow and Brad Pitt

Gwyneth Paltrow and Brad Pitt’s romance started on the set of the David Fincher thriller, Se7en back in 1995. Pitt was 31 years old and already had a burgeoning career, while Paltrow was only 22 and was just starting to learn her way around show business. The couple was obsessed with each other and refused to work every second of being single. They were one of the most popular couples during this era.

The following year, in 1996, Pitt proposed to the actress. Back then, they were inseparable, and they were so giddy about their love for each other that Brad even gushed about how excited he was to start a family with Gwyneth in the future. They dated for a total of four years and decided to end things in 1997. Since then, the two went their separate ways. The investments they have now in their separate lives are worth it.