Ivanka Trump used to make headlines for who she was dating, not for allegedly bending the ethics guidelines of Donald Trump's White House. Her dating history began with long-term boyfriend Greg Hirsch, whom she met at Georgetown University and broke up with in 2001.
Ivanka moved on to James "Bingo" Gubelmann, a fellow socialite, and she even appeared in the Gubelmann-produced documentary "Born Rich," but the two split in 2005. Her next celebrity fling was actor Topher Grace; Grace later admitted they had a connection, but denied ever meeting Ivanka's dad.
Ivanka was also tied to Justin Murdock, heir to the Dole fruit fortune, and Sean Brosnan, son of Pierce Brosnan. Perhaps the most shocking chapter of Ivanka's dating history is Quincy Jones; the Motown legend claimed that Ivanka asked Tommy Hilfiger to introduce them, despite the 48-year age difference.
In a twist of fate, Jones may have been a less scandalous partner than Jared Kushner, whom Ivanka married in 2009. Not only did the couple defy anti-nepotism rules with their White House positions, but a government watchdog found that they made up to $640 million during Ivanka's father's term.