13. Claire Danes
Leo spent a golden year with his Romeo & Juliet co star Claire Danes.The two dated from 1995 to 1996. If you started a fling on-screen, why not try it out off-screen right? The American actress is truly a classic babe. With her blonde hair and blue eyes, she was right up Leo’s alley. The beautiful actress found her stardom as Angela Chase in My So-Called Life.