Before settling down with real estate developer Jared Kushner, Ivanka had her share of famous boyfriends. In 2006, she went on several dates with Lance Armstrong, but according to People, “the relationship never got out of first gear.” And, yup, that was a bike pun. Sorry about that.
However, Ivanka quickly rebounded that same year with That ’70s Show star Topher Grace, and People reported the two were spotted getting very close at her 25th birthday. But things quickly fizzled just like with Armstrong, and it turns out the problem was bringing them home to meet dad.
“I was too smart to bring home a date or a boyfriend,” Ivanka told CNN (via the New York Post). “I was not going to subject boyfriends to the scrutiny of my father or mother, for that matter, unless I was 100 percent sure.” While Ivanka would ultimately subject her now husband Kushner to Donald Trump for inspection, that didn’t stop her taste for famous men.