Meet the 6 Men That Dated Ivanka Trump Before Jared Kushner (2 of 4)

2. Sean Brosnan

Back in 2007, Ivanka pretty much dated Agent 007’s son. We are, of course, referring to Sean Brosnan, whose dad Pierce starred in four James Bond movies from 1995 through 2002. Although the younger Brosnan has never achieved his father’s level of stardom, he’s made a modest living as an actor and director. For whatever reason, things didn’t work out between Sean and Ivanka. In fact, the relationship never got to the point where Trump brought him home to Daddy.

3. Greg Hersch

These two lovebirds met during their freshman year at Georgetown University, where Ivanka studied for two years before transferring to Penn. Greg must have been a real charmer because he managed to convince Ivanka to move in with him pretty early in their relationship, and they even adopted a yellow Lab named Tyler, a true sign that things were getting plenty spicy. But, alas, it wasn’t meant to be. The couple called it quits in 2001. But don’t feel too sad for ol’ Gregory. He’s doing quite fine as the founder of Florence Capital, a successful money management firm.