[custom_adv] Bridget Hall According to a 1998 gossip item in the london sun, Leo dumped the model his very first! after a "night of love"she found disappointing. [custom_adv] Naomi Campbell Leo's 1995 rumored filing with Naomi Campell reportedly fizzled fast, but they became good freinds. [custom_adv] Kristen Zang Kristen Zang a model who dated Leo for two years (1996-1998) accompanied the actor to the premier of Romeo+Juilet. [custom_adv] Gisele Bundchen before tom brady, Gisele Bundchen dated Leo for five years, but ended it in 2005. [custom_adv] Bar Refaeli Leo moved on to another Victoria's Secret model, Bar Refaeli, who shared his passion for activism. [custom_adv] Kelly Rohrbach Leo began dating Kelly Rohrbach, a former prep schooler, D1 golfer, Georgetown university grad and yes, sports illustrated model in the spring of 2015. [custom_adv] Madalina Ghenea They met while he was shooting the great Gatsby in Australia. [custom_adv] Blake Lively Leo's 2011 whirlwind romance with Blake Lively started out with domestic bliss. [custom_adv] Rihanna Leo and Rihanna apparently shared a "flirtatious" night in the Paris club in January, though tabloids reported the two had a fling going on long before.