Meet the 6 Men That Dated Ivanka Trump Before Jared Kushner (3 of 4)

4. Lance Armstrong

Well, here we are. After profiling two pretty normal exes, Ivanka’s relationship with one of the greatest cheaters of all time marks the point where things really go downhill. Armstrong, who vacated 7 Tour de France when it was discovered that he had doped his way into winning them, is rumored to have dated Trump after they bumped into each other in Los Angeles, where Ivanka had gone to film scenes for “The Apprentice.” When commenting to People, Ivanka suggested that no romance was taking place between the two, so it might have been one of those Friendzone deals.

5. James “Bingo” Gubelmann

Socialite James “Bingo” Gubelmann came into the picture after Ivanka ended her relationship with Hersch, and it lasted nearly four years. As they had both grown up in New York, hung out within the same elite social circles, and had attended glitzy private schools, they certainly had plenty in common. While they were an item, Bingo produced a documentary called “Born Rich,” which was pretty much about his friends, and in which Ivanka appeared in a few scenes. She announced their breakup during an appearance on “The Tonight Show With Jay Leno,” you know, like any normal person would. On a side note, ladies, never date a guy who insists on being called “Bingo.” Have some respect for yourself.