Among those rumored, but unconfirmed girlfriends: Demi Moore, Blake Lively, Rihanna, Naomi Campbell, and Paris Hilton.
What's more, in the past few days alone, the actor has allegedly set his sights on Bella Hadid, though every bit of Cannes-filled drama should be taken with a grain of salt.
He hooked her up with her first big Hollywood connection, director James Toback, who cast Bijou in his film Black and White.
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Before Tom Brady, Gisele Bündchen dated Leo for five years, but ended it in 2005.
"We were just not meant to be boyfriend and girlfriend, but I respect him enormously, and I wish him nothing but the best," she told Access Hollywood in 2009.
He failed to take her as his date to the Oscars last month, even though they have been dating for around nine months.
And Nina Agdal gave a cold shoulder to Leonardo Di Caprio on Wednesday - in a literal sense at least.
Agdal is famously just the latest model ex for the perennial single actor, who over the years has dated a number of high-profile glamazons, particularly of the Victoria's Secret variety, including Gisele Bündchen, Toni Garrn, and Bar Rafaeli, to name a few.