Meet the 6 Men That Dated Ivanka Trump Before Jared Kushner

Before Ivanka Trump and Jared Kushner merged into what many now jokingly call “JaVanka,” Donald Trump’s eldest daughter had a surprisingly varied dating history. Long before she settled into her role as part of a political power couple, Ivanka was linked to a string of high-profile, wealthy, and well-connected men—some seemingly respectable, others raising plenty of eyebrows. From polished businessmen who fit neatly into the Trump brand to relationships that felt messy, mismatched, or downright questionable, her romantic past offers a revealing glimpse into the world she moved through. Here’s a look at six of Ivanka’s rumored or confirmed partners, ranked from most reasonable to truly dysfunctional.

1. Topher Grace

Topher Grace seems to be the most normal of the “That ’70s Show” cast, but he seems to have regrets about being linked to Ivanka, downplaying the relationship in an interview with The Daily Beast. Among other things, he pointed out that it was back in 2008, several years before Donald Trump was elected president. He also questioned whether what they did could actually be considered “dating.” Well, People reported at the time that they were seen together at Ivanka’s 25thbirthday celebration at a Las Vegas nightclub and even engaged in some kissing and cuddling. So there you have it. Checkmate, Mr. Grace!