14. Blake Lively
Although never officially confirmed, Leo and the absolutely gorgeous Blake Lively were spotted in a variety of local bars and clubs in 2011. Apparently the relationship fizzled (much like Lively’s career).
After a promising start to her career, beginning with her standout role in The Sisterhood of the Traveling Pants, Blake’s career has seemed to stalled after her falling out with Leo. Perhaps her role in an upcoming untitled Woody Allen project will help revitalize her career. But I wouldn’t be too worried if I were her, she is married to Ryan Reynolds, who is a rising star in Hollywood.