Ivanka Trump's Relationship History Before Jared Kushner

Ivanka Trump got together with husband Jared Kushner in 2007. Since then, we've become used to seeing him by her side (apart from the period of time they had broken up in 2008). Ivanka had this to say to Vogue about meeting her husband after being introduced by mutual friends: "They very innocently set us up thinking that our only interest in one another would be transactional," she said in 2015, before adding, "Whenever we see them we're like, the best deal we ever made!" 

When speaking with GQ in 2007 about the type of guy she tends to go for, the person she described interestingly sounded similar to her husband. She said, "I like very strong guys. Successful guys. Not necessarily financially. But that said, I'm not one of those people who would be with somebody who didn't have their finances in order, because that's not a way to live." She added, "Honestly, I have a tendency to date dorks. Which means that a lot of times, I date guys that no one else would deem to be a hunk."

However, the mom of three, socialite, businesswoman, and former wingwoman for her father Donald Trump's 2016 presidential campaign and presidency had a life before her husband. The former model's relationship history includes several long-term and brief relationships, from her longtime college boyfriend to her film producer ex to a well-known athlete and an actor. Curious to learn more? These are Ivanka Trump's relationships (actual and rumored) before Jared Kushner.

We've all had a first love, and for Ivanka Trump, that first love was future investment banker Greg Hersch who has since launched wealth management firm Florence Capital. Trump spent her first two years of college with Hersch, whom she dated both before college and while studying at Georgetown University prior to transferring to the University of Pennsylvania's prestigious Wharton School of Business. Apparently, the onetime couple lived together for a time and even adopted a yellow Labrador together before going their separate ways in 2001. The former couple had also been pictured walking their dog during their time together.

Regarding her relationship with Hersch, Trump said in an interview with GQ that nothing dramatic had happened. "We were in college. It was actually a little before college," she said, adding, "There's never been, you know, name slinging, hatred. It's more, 'That's it, we're done.'"

Ivanka Trump shared with GQ in 2007 that her first two relationships lasted almost four years and were pretty much back to back. Not long after splitting up with Greg Hersch, she began dating James "Bingo" Gubelmann, a wealthy socialite-turned-film producer who grew up in the same circles as Trump and who, like her, attended prestigious New York City private schools. In 2003, he produced the documentary "Born Rich," in which Trump appears. Other films he's produced include "The Runner" and "My Son, My Son, What Have Ye Done?"

According to Trump, the demise of her relationship with Gubelmann was similar to that of Hersch. "I think both relationships ran their course. They just got to a point where we weren't making each other happy any longer," she told GQ, adding, "I believe in fighting for a relationship. But you know what? It shouldn't be that difficult at this age. If you can't be happy at this age, when you're young and in love, you're not gonna be happy in [20] years."

The former couple dated until 2005 when Trump announced their breakup while appearing on "The Tonight Show With Jay Leno." Many years later, Gubelmann made headlines for getting arrested alongside Mickey Madden, bassist for Maroon 5, in New York City on drug possession charges. He allegedly attended a treatment program following the incident as part of his agreement.

After her breakup from James "Bingo" Gubelmann in 2005, Ivanka Trump spent the next couple of years dating and flirting, including with some seemingly unlikely suitors. The first is disgraced cycling great Lance Armstrong. The two were said to have gone out a few times after meeting at a charity event in Los Angeles while Ivanka was in town filming the popular NBC reality series "The Apprentice" with her dad, Donald Trump. According to sources who spoke with People, there wasn't much to tell — it was just a case of two people who, in the end, didn't really click.

Both she and the athlete denied rumors of any alleged fling in 2006. At the time, Ivanka told People, "I have tremendous respect for Lance and all he has accomplished. That said, we are just friends."

Speaking of friends, Ivanka has said it's not easy to remain friends with her exes though she has managed to do so. "I marvel at how people do it so seamlessly," she told GQ in 2007.

In November 2006, Ivanka Trump was seen getting cozy with "That '70s Show" star Topher Grace at Pure nightclub in Las Vegas while celebrating her 25th birthday at a party attended by stars including Adam Levine and Chelsea Handler. As reported by People, the two cuddled and kissed on a VIP bed before leaving together, holding hands.

Neither Ivanka nor Topher or their reps confirmed or denied anything about the relationship to the media, with the actor's rep only telling People, "I don't comment on Topher's personal life."

Many years later, he put the rumors to rest when asked about his former dalliance with Donald Trump's daughter during a 2018 interview with the Daily Beast. "Uh... I did," he admitted. "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."

In a 2007 interview with GQ, Ivanka Trump spoke of being newly single after being in two long-term, back-to-back relationships, emphasizing at the time her confidence and aptitude for flirting. "I've never been at a place in my life where I've felt, quite frankly, sexier and more comfortable with my body. And sort of more in touch with myself. Generally, my self-esteem on every level is probably at a peak. So in a dating situation, I found out I'm a pretty good flirt," she said, "that I know how to do it rather well."

Perhaps this was her frame of mind when engaging in her next brief romance with Dole heir Justin Murdock, a guy who doesn't sound to be all that different from her ex, James "Bingo" Gubelmann. Insider referred to Murdock as a "bad boy," while a 2008 Forbes feature described him as hanging out in celebrity circles which included Aerosmith's Steven Tyler and having gone "through a goth rock phase" while performing in Los Angeles clubs years prior. The businessman later went on to date singers Lana Del Ray and Avril Levigne before getting serious with Francesca Eastwood, granddaughter of Clint Eastwood, in 2017.

The last of Ivanka Trump's reported dalliances before settling down with Jared Kushner was with actor Pierce Brosnan's son, Sean Brosnan. Like his famous father, Sean is an actor as well as a director who has appeared in various movies and television shows. Allegedly, at the time he dated Ivanka, Sean had completed work on a TV mini series called "When Evil Calls" and had a number of other projects in the works.

Apparently, Ivanka took Sean as her date to the 50th Annual International Red Cross Ball at Mar-A-Lago in January 2007, as the two were pictured posing together at the event. However, even while appearing as her date, it's said that Sean never met Ivanka's famous but intimidating dad, Donald Trump. "I was too smart to bring home a date or boyfriend," the former first daughter said to CNN in 2016 (via Insider). "I was not going to subject boyfriends to the scrutiny of my father, or mother for that matter, unless I was 100% sure." During that same interview (via the Daily Star), she also said, "I think I brought home my husband, that's it."

This next "relationship" really wasn't much of a relationship, as it has been denied by Ivanka Trump's rep, and, honestly, we don't believe there is any truth to it ourselves. But it's interesting to mention that music mogul Quincy Jones, who is older than Trump's father, once alleged in a bizarre 2018 interview with Vulture that he had dated Trump. "I used to date Ivanka, you know," he said during the interview, continuing to say, "Twelve years ago. Tommy Hilfiger, who was working with my daughter Kidada, said, 'Ivanka wants to have dinner with you.'" Of Trump, Jones said, "She had the most beautiful legs I ever saw in my life. Wrong father, though."

Shortly following that interview, E! News confirmed that a source close to Trump alleged the claim to be far from the truth. This one just leaves us shaking our heads.