Shortly after Gwyneth and Brad called off their engagement, he famously began dating Jennifer Aniston. Of course, it wasn’t long before Brad and Jen were engaged, and by the year 2000, they were married. Their marriage was ultimately short-lived, with the pair announcing their separation early in 2005.

Gwyneth Paltrow is said to have been filled with pain over Brad Pitt ’s marriage to Jennifer Aniston in 2000. The Shakespeare in Love actress is said to have revealed her agony while speaking at the 2000 Toronto Film Festival, when a journalist’s query about her ex-fiancé’s nuptials caught her off guard, RadarOnline.com can reveal.