A "bad boy," an athlete, and an actor. Before saying "I do" to Jared Kushner,
Ivanka Trump was with these men.
"First love, do you even- even remember who it was? Yeah, I do."
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. She dated him 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.
Regarding her breakup with Hersch,
Trump said in an interview with GQ that nothing dramatic had happened, adding,
"We were in college. It was actually a little before college. [...] 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. Like her, he 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. She told GQ,
"I think both relationships ran their course. They just got to a point where
we weren't making each other happy any longer. 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 twenty 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.
"You're fired." 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, Trump told People,
"I have tremendous respect for Lance and all he has accomplished. That said, we are just friends."
Speaking of friends, Trump has said it's not easy to remain friends with
her exes though she has managed to do so. She told GQ in 2007,
"I marvel at how people do it so seamlessly."
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. As reported by People,
the two cuddled and kissed on a VIP bed before leaving together, holding hands.
Neither Trump nor Grace 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. He admitted,
"Uh... I did. 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, saying
"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. 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 that included Aerosmith's Steven Tyler.
The last of Ivanka Trump's reported casual relationships before settling down with
Jared Kushner was with actor Pierce Brosnan's son, Sean Brosnan. Like his famous father,
Brosnan is an actor as well as a director who has appeared in various movies and television
shows. Allegedly, at the time he dated Trump, Brosnan had completed work on a
TV mini series called "When Evil Calls" and had a number of other projects in the works.
Apparently, Trump took Brosnan 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 Brosnan never met Trump's famous
but intimidating dad, Donald Trump. The former first daughter said to CNN in 2016,
"I was too smart to bring home a date or boyfriend. 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 she also said,
"I think I brought home my husband, that's it."