Brad Pitt And Jennifer Aniston Didn't Date For Years After They First Met

In 1998, Brad Pitt and Jennifer Aniston's managers conspired to bring them together again. Aniston was no longer with Tate Donovan and Pitt had famously called off his engagement to Gwyneth Paltrow. This time around, sparks flew. Speaking to Diane Sawyer in 2004, Aniston described her date with Pitt as "a really easy evening. It was really fun," (via YouTube). The following year, Aniston and Pitt made their official red carpet debut at the Emmy Awards. 

Aniston wore a brown sequined gown, whereas Pitt looked peak '90s with his tiny silver sunglasses and spiked hair. Also in 1999, Aniston and Pitt made a typically high-profile public appearance at a Sting concert, in which Aniston revealed her blinding diamond and platinum engagement ring. Not just any bauble, Aniston's engagement ring was specially designed by Pitt in collaboration with Silvia Damiani and apparently took him seven months to perfect.

On July 29, 2000, Aniston and Pitt married in California, with the "Friends" star wearing a gorgeous, sleeveless Lawrence Steele gown. That year also marked their first appearance as a married couple at the Emmys, two years after their first red carpet. When 2001 rolled around, Pitt had a cameo on "Friends" as a character who (ironically) hates Rachel Green, the beloved character played by Aniston. Up until then, things seemed perfect.