As a result, he went out with an incredibly full list of leading actresses, from Robin Givens to Juliette Lewis to Jennifer Aniston. After marrying Angelina Jolie and having six children, it seemed like he left the dating scene for good.
You never forget your first fiancé. Pitt and his Cutting Class co-star were engaged for eight months in 1989, but their flame died out when the two met in Budapest, Hungary.
Brad Pitt and Jennifer Aniston first met in 1994, but their relationship didn’t really start until 1998. Brad proposed to Jennifer in 1999 and they married the following year. After five years of marriage, the couple announced their separation in early 2005.
Leonardo DiCaprio was never married
The 47-year-old has had several relationships over the years. But DiCaprio has never really committed to any of the women by getting engaged or married.