Gwyneth Paltrow and Brad Pitt
Gwyneth Paltrow and Brad Pitt dated from 1994 until 1997, with the two even getting engaged while Paltrow was just 24 years old. However, they ended up separating, with Paltrow admitting that she was not feeling ready for marriage quite yet. She eventually marries Coldplay frontman Chris Martin and Brad Pitt married Jennifer Aniston.
January Jones and Ashton Kutcher
In the late 1990’s, Ashton Kutcher and January Jones were still not quite household names. They both worked as models for clothing brand Abercrombie & Fitch, which is when they met and began dating. The couple lived together for a time but eventually broke up, with Jones saying that dating “is too hard in this town [Hollywood].”