Click through the gallery below to get an in-depth look at alllll the girls Ty has, quote-unquote, dated!In our continuing series taking a look at some of most legendary ladies men, today we will discuss the alleged sexual history of Leonardo Di Caprio. Note: There are so many we’re just going to combine years with a few in the interest of brevity. Last month a different woman—23-year-old Ford model Victoria Lee Robinson—was seen leaving Justin Bieber’s Purpose tour after-party in New York City with Di Caprio.Weeks before that it was 24-year-old Instagram star Roxy Horner on Leo’s arm, and recently the toxic bachelor was reportedly wooing 19-year-old model Chelsey Weimar. Rihanna, Kelly Rohrbach, Erin Heatherton, Toni Garrn–hell, you name a model, and we’d safely bet she’s linked with Di Caprio. In the slideshow ahead we’ve rounded up every woman Leo’s dated, may have dated, and probably didn’t date (but we all wildly speculated about anyway).Meanwhile, regardless of how real the connection was, pretty much every year of Spade's life since the mid-90s is accounted for when it comes to being linked, attached, rumored to be dating or actually dating someone.actress Kelli Mc Carty, who was crowned Miss USA in 1991 and hooked up with Spade not long afterward, according to a story she told Howard Stern.Witnesses told TMZ that the pair smoked for a few hours in the lounge area at The Crows Nest restaurant before heading inside for dinner, and they were seen getting breakfast at Goldberg’s Famous Bagels.
Sure, it took him a couple of decades to finally cop that Oscar, but considering all of the other fly sh*t he has going on, do you think he really gives a damn?The man who was once in charge of “The Pussy Posse.” Derek Jeter’s sexual history is impressive, Wilder Valderrama’s is mind-boggling, but neither of them hold a candle to Leo. A hot actress and two supermodels, Leo was just getting started. Leo now has under his belt, giving him even more ammunition, and he uses it wisely. Leo, being the savvy guy that he is, briefly took advantage of Sienna and Jude Law’s relationship issues. And it did for a long time, but we should have known better. According to the legend told by Bobbie herself, a 19-year-old Leo sang her “Waterfalls” by TLC and that's pretty much all it took for her to give it up.These two met while partying, and Leo helped Bijou jumpstart her acting career by introducing her to the director who ultimately cast her in her first movie.