Claire Forlani: The Beginning

His age: 35

Duration: 1998

Following his split from Gwyneth Paltrow, Brad Pitt reportedly began a brief romance with his Meet Joe Black co-star, Claire Forlani. While the courtship might not have been forever, the pair were excited to see where things would lead.

The budding relationship attracted attention when the pair attended the 50th Annual Writers Guild of America Awards together, sparking speculation about their romantic involvement.