Yesterday, news broke that Leonardo DiCaprio, the Hollywood actor who has somehow only won one Academy Award, and model Camila Morrone had broken up after four years of dating. Of course, many were quick to jokingly suggest that DiCaprio must’ve dumped Morrone because she’s now 25 years old – DMARGE did a deep dive into DiCaprio’s dating history and indeed, Leo, who is 47-years-old hasn’t dated anyone over the age of 25.