Gwyneth Paltrow: The Beginning

His age: 32-34

Duration: 1995-1997

Brad Pitt and Gwyneth Paltrow’s love story began on the set of the 1995 thriller Se7en, where Paltrow portrayed Pitt’s wife. Their on-screen chemistry translated into a real-life romance, with Pitt publicly declaring Paltrow as his “angel” and the “love of [his] life” during his 1996 Golden Globes acceptance speech.

Their engagement in December of that year solidified their commitment to each other, promising a future filled with love and happiness. But seeing as the pair have since been married and had entire families with other people, something clearly didn’t work out.