46.Ben Affleck and Gwyneth Paltrow

In 1997, just after Gwyneth Paltrow and Brad Pitt split, she started a romance with Ben Affleck. Though their relationship lasted for three years, with the actress admitting that she did not see herself marrying him.Paltrow and Affleck first met during a dinner. They starred in the films Shakespeare In Love and Bounce. Their relationship was well-received by the media as they were both at the peak of their careers at the time.

In 2000, the two split and did not say a word about it until in recent years when Paltrow spoke about her past relationships during an interview. She mentioned how she knew that she and Affleck were not going to end up together as she was still in the healing process from her previous relationship to some degree. She added that he was kind of complicated in terms of handling relationships. Additionally, she mentioned that their differences, especially in terms of values, made them incompatible in the long run.