Before they tragically became one of the most influential families in American politics, the Trumps were busy rubbing shoulders—more like hooking up—with Hollywood’s crème de la crème. (Photos: WENN)
Topher Grace recently confirmed his relationship with Ivanka Trump back in 2006. “Certainly it wasn’t a political statement. This was a decade ago. I met her here in New York and we went on a couple of dates.” (Photo: WENN)
Just a few days ago it was reported that Donald Trump Jr.’s new girlfriend is Kimberly Guilfoyle, a now-former Fox News host for the afternoon show “The Five.” Though they just started dating, Guilfoyle and Trump have known each other for at least a decade! (Photo: WENN)
Not a celebrity per se, but porn star Stormi Daniels is quite famous in the adult film industry—and she allegedly dated Donald Trump in 2006 and was even threatened to stay silent about the affair. “He would call al the time,” a friend of Stormi revealed. (Photo: WENN)
Though its unclear if Ivanka Trump and Tom Brady actually date, former White House communications director Scarmucci seems to think so. “Maybe there was a relationship between him and Ivanka at some point.” I bet Gisele disagrees! (Photo: WENN)
Donald Trump Jr.’s marriage began its downward spiral in 2011 when he cheated on Vanessa with Danity Kane singer and “Celebrity Apprentice” contestant Aubrey O’Day. She even hinted at the alleged fling with her song “DJT”—which we all know what they stand for. (Photo: WENN)
Brooke Shields didn’t actually date a Trump, but Donald did try to ask her out. “‘I really think we should date, because you’re America’s sweetheart and I’m America’s richest man, and the people would love it,’” she recalls him saying. YIKES! (Photo: WENN)
Ivanka’s dating history includes the progeny of our favorite 007 Agent, Pierce Brosnan’s son Sean. Brosnan reportedly managed to get cozy with Ivanka at a charity event in 2007, even though he is two years her junior. Cougar alert anyone? (Photo: WENN)
“Real Housewives of Beverly Hills” star Kim Richards could have been first lady of the United States. The 52-year-old revealed she once dated Donald Ttrump. “I had a dinner with him. I had dinner with Donald Trump.” (Photo: WENN)
She just divorced Donald Trump, though in paper, Vanessa is still a Trump, and she allegedly briefly dated Leonardo DiCaprio when she was only 20 years old. The two were seen together a couple of times during the 90’s. The Rose to his Jack maybe? (Photo: WENN)
Can you imagine a world where Brooke Shields is First Lady? Or Leonardo DiCaprio is senior White House advisor? Or where Patriots’ quarterback Tom Brady is son-in-law of the President of the United States?
All of the above could’ve happened if the Trumps’ love life had turned out to be just slightly different.
Before they tragically became one of the most influential families in American politics, Donald Trump, his oldest son Donald, and his favorite daughter Ivanka were busy rubbing shoulders—more like hooking up—with Hollywood’s crème de la crème.
So it shouldn’t come as a surprise that Topher Grace isn’t the only star who has been in a romantic, or at least physical relationship with one of the Trumps, as he recently confirmed in an interview with the Daily Beast.
Click through our photo gallery above and see all the celebrities you didn’t know had dated the Trumps over the years. And by celebrities we also mean adult-film stars who were paid to keep silent about their extramarital encounters.
