Gwyneth Paltrow and Ben Affleck
In 1997, Gwyneth Paltrow began dating Ben Affleck, and the two dated on and off until 2000. They met while appearing in Shakespeare in Love together. After they broke up, Affleck began dating Jennifer Lopez, proposing to her for the first time not long after. After Ben and Jen got married 20 years later, Paltrow posted a supportive message on Instagram.
Gwyneth Paltrow And Ben Affleck (Kevin Mazur/Inactive/Getty Images)
Melissa Gilbert and Rob Lowe
In 1980, Melissa Gilbert and Rob Lowe began dating, and were together for seven years. In 1986, he proposed to her, but just one year later, they had called in quits. Just seven weeks after their breakup, Gilbert married actor Bo Brinkman in 1988.
Melissa Gilbert and Rob Lowe (Time Life Pictures/DMI/The LIFE Picture Collection/Getty Images)
