Top 12 celebrities with the longest dating rosters – See who’s number 1! (With Pictures)

4. Leonardo DiCaprio

You can call him a debonair leading man, a tour de force actor or an international man of leisure. Whatever you call him, just be prepared to acknowledge that Mr. Di Caprio has dated some of the most beautiful models in the world. We don’t know how he does it, but this guy certainly has the Midas touch. Some of the hot models and actresses he has dated include: Gisele Bundchen, Bar Rafaeli, Erin Heatherton , Blake Lively, Kelly Rohrbach and Toni Garrn. Wow! – This guy is certainly living the life.