34. Orlando Bloom and Kate Bosworth

Orlando Bloom and Kate Bosworth dated in 2002, but unfortunately, their romance ended in 2005. Their love story is perhaps one of the most heartbreaking stories we have had with us during our childhood. Bloom was a heartthrob, credits to his role as Legolas in the Lord of the Rings franchise. During the peak of his fame, he announced to all the ladies in the world who were falling in love with him that a certain lady has already won his heart. Just as all hearts were healed and fans turned their sadness in to rooting for these two, they announced that they decided to split up.

They were even engaged at one point. Bosworth was the first serious relationship Bloom had in Hollywood. They were young but they were so in love. After their breakup, it changed the actress’ life forever and it also made her vow never to date actors again. There was something in her relationship with Bloom which made her promise to herself that she can’t be involved with a celebrity romantically. It served as a wakeup call.