A Resurfaced Ivanka Trump Report Reminds the Internet That She Used to Date This A-List TV Star

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Ivanka Trump has been happily married to Jared Kushner since 2009, but during her single days, she dated a very familiar TV face. The internet seems to have forgotten about this former couple, but a resurfaced report is reminding everyone that Donald Trump’s oldest daughter could have had a very Hollywood life.

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We have to flashback to 2006 at Ivanka’s 25th birthday in Las Vegas where she and That ’70s Show star Topher Grace were spotted canoodling in the VIP area of Pure nightclub. They were hanging out with Chelsea Handler, Adam Levine, and Ryan Cabrera, according to People, as they celebrated her big day. Nobody really remembered this early aughts moment until Ivanka’s father ran for president and won. In 2018, fans have The Daily Beast to thank for resurrecting this random coupling and putting them back into our pop culture timeline.

Grace didn’t sound exactly thrilled to relive this part of his life, not because of Ivanka, but perhaps because of her controversial father. “Uh… I did,” he confirmed to the media outlet that they dated years ago. “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. I wouldn’t say that we ‘dated,’ but… I didn’t do it for political reasons.” He also attempted to distance himself from Donald Trump by revealing that he “never met her father.” So, let’s just say this was a casual romance because the next guy she dated after Grace was Kushner.

Kushner wasn’t the son-in-law Donald Trump was hoping for because the former president was trying to play matchmaker between Ivanka and Tom Brady. In the 2022 book, Breaking History: A White House Memoir, Kushner tried to discuss his proposal details and Ivanka’s conversion to Judaism to his future father-in-law who wasn’t exactly thrilled over the prospect. “Well, let me ask you a question,” Donald Trump asked his future son-in-law. “Why does she have to convert? Why can’t you convert?” He went on to remind Kushner that Brady was interested in Ivanka, so she had plenty of marriage options.

Brady had very different ideas about his dating life, though. In a 2020 interview with Howard Stern, the former NFL star downplayed any association with the former White House senior adviser. “That was a long time ago in my life,” Brady answered awkwardly. “No, there was never that where we ever dated or anything like that.” It sounds like it was more a dream date for Donald Trump than it was for anyone else.

Before you go, click here to see surprising celebrity couples we never saw coming.

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