Paris Hilton's Most High-Profile Relationships

If anyone knows you have to kiss a few frogs before you meet your prince, it's Paris Hilton. She went through the romantic wringer during her journey to living ever after, encountering a mix of Mr. Rights, Mr. Right Nows, and Mr. Just Plain Wrongs along the way. Still, she eventually found the one in her husband, Carter Reum.

Hilton and Reum's relationship is a far cry from some of her previous trainwrecks, which were frequent and bountiful. During the early noughties, Hilton changed boyfriends more than Juicy Couture sweats, tossing them aside like a Von Dutch trucker cap when she was done. Still, that's not to say she didn't suffer more than her fair share of heartbreak and adversity. Those experiences resulted in some important life lessons and ultimately contributed to Hilton's transformation from Hollywood party girl to married mom-of-two.

These days, Hilton's dropped the breathy, ditzy airhead act. However, her inner pampered princess still rears its head occasionally, as evidenced by the number of dresses Hilton wore during her November 2021 wedding celebration — six out of the custom-designed 45 she had on standby: a Galia Lahav, a Pamella Roland, three Oscar de la Renta, and a Marchesa, in case you were wondering. Still, Hilton's positively low maintenance now, compared to her bachelorette years, which were packed with paparazzi and drama — something her army of exes can attest to. From bad boys to soulmates, Greek heirs to hookups, Hilton's most high-profile relationships garnered their fair share of headlines over the years.

It's safe to say that Paris Hilton's first love is one she will never forget, no matter how hard she tries. Rick Salomon made sure of that by leaking a sex tape they made in 2001 when she was 20 and he was 32. Hilton was in Australia when a 37-second clip of it surfaced in 2004. She begged Salomon not to leak any more footage, but he ignored her pleas. "It was the most embarrassing, the most humiliating thing that's ever happened to me in my life," Hilton told Piers Morgan in June 2011. "...I just felt so betrayed. This was not some random guy; this was someone I was with for a few years," she continued, admitting she thinks Salomon is "a very bad person."

After "1 Night in Paris" was released, Hilton filed a $30 million lawsuit against Kahatani Ltd, the tape's online distributor. However, The New York Daily News reported that she was forced to settle for $400,000 after her case was dismissed. Hilton claims she got zero, though. "Never made a dollar," the socialite told TMZ in November 2013, insisting she'd never even attempted to broker a deal. "I make enough money in nice ways," Hilton said.

Meanwhile, the flick won three awards at the 2005 AVNs, the adult industry's version of the Oscars. And according to his tax filing, Salomon earned $10 million in the first year of the tape's release, the vast majority from its sales.

Paris Hilton made the most out of being young, blonde, and beautiful in early aughts Hollywood, cycling through a slew of hot hookups as she sowed her wild oats. Hilton was a fixture on the club scene and in the tabloids as she fell out of limos, flashed her pantiless bits for eager paparazzi, and knocked back champers at Les Deux.

Among Hilton's high-profile relationship hookups was Sum 41 frontman Deryck Whibley. He casually dated Hilton for a few months in 2003. "We were running in the same circles at certain events, and one night, we bumped into each other and just started talking," Whibley told GQ in December 2023. "I was maybe 22, she was 21, and we hit it off. She's a very fun party girl, we were a party band. It was just fun."

Benji Madden was another musical friend with benefits. He and Hilton went on double dates with Joel Madden and Nicole Richie for a while. "It's actually perfect," Hilton told David Letterman in May 2008. "We're like sisters, and they're twins, so it works out well," she continued. "... I'm so happy, I'm so in love." However, it was all over within nine months. Still, Hilton always had Simon Rex to fall back on. The two were in a booty call situationship from 2004-2010. "She'd come out to the club on roller skates," Rex told Vulture in November 2021. "She'd roll up to guys and be like, 'You're so hot.'"

Paris Hilton's dating history is peppered with drama and toxicity. "I went through multiple abusive relationships," she told People in September 2020. "I was strangled, I was hit, I was grabbed aggressively. I put up with things no one should." Hilton didn't name names, but it's pretty easy to speculate about who one of them is. Nick Carter reportedly left Hilton black-and-blue and "scared to death" during their six months together. "He has major anger-management issues. We have seen bruises on her before and asked her about them," a friend told The New York Post in July 2004.

Meanwhile, Joe Francis alleged Hilton attacked him when he ended their drama-packed pairing in 2003. "I had to call the security of [the hotel], and then she started beating me because she was drunk," he said in a 2022 episode of "Behind the Velvet Rope with David Yontef." Hilton and Cy Waits' tumultuous one-year trainwreck was equally dramatic. They were arrested together in August 2010 after Hilton was found with cocaine in her purse. Four months later, she was caught on camera whacking him across the face during an explosive Cabo San Lucas New Year's fight.

Hilton's one-year romance with Doug Reinhardt was seemingly also packed with theatrics and fire. According to TMZ, a November 2009 "knock down drag out" fight between the couple sparked by Hilton begging Reinhardt not to leave resulted in cops being called to her house.

Paris Hilton landed herself not one but two Hellenic hunks during her dating Greek era (2004 to 2007 AD). Both of them were filthy rich, and one of them proposed to her with a humungous sparkler. The lady said yes, natch.

First up was Paris Latsis, the grandson of multi-billionaire shipping tycoon Yiannis "John S." Latsis. It's safe to say that Hilton's bank balance paled compared to Paris L's. According to Forbes, his family is worth $2.2 billion, making for a tidy inheritance when his father, Spiro Latsis, dies. Paris Squared started dating in December 2004, and he proposed in May 2005 with a $4.7 million 24-carat emerald cut diamond flanked by two trapezoid baguette diamonds. Hopefully, he kept the receipt because five months later, they were done. "I will always love him," Hilton told People in October 2005. "He treated me like a princess the entire time."

Still, she quickly moved on. Just hours after the news of their split broke, Hilton was spotted getting down with another shipping heir, Stavros Niarchos III. And he was even richer than the last, with Forbes estimating Stavros' father, Philip Niarchos, is worth $2.8 billion. There was drama galore between Hilton and Stavros. Their on-off relationship was tumultuous and drama-packed — including a Mary-Kate Olsen, Hilton, and Niarchos love triangle and a Hilton vs Lindsay Lohan showdown. The tabloid two finally called it quits in May 2007.

Paris Hilton has had her share of Mr. Rights. River Viiperi was one for two years. He called Hilton his "future wife" in May 2013 before they split in July 2014. Thomas Gross only lasted a year. "Soulmates," Hilton gushed in a July 2015 Instagram post that's since been deleted (via Hello!).

Making for a fabulous ring collection, he's also had her share of fiancés. Hilton's been engaged a whopping four times: Jason Shaw, Paris Latsis, Chris Zylka, and, of course, her current husband, Carter Reum. Shaw proposed in 2002 with a pear-shaped diamond estimated to be worth $1 million. However, they were done by 2003. Latsis was squeezed in for five months in 2005, then Chris Zylka was up. He popped the question in January 2018, presenting Hilton with a 20-carat diamond ring worth $2 million. She called him "the love of my life and my best friend" but kicked him to the curb ten months later. Then, she finally found her happy ever after.

Hilton and Reum knew each other for over a decade before getting hot and heavy following a Thanksgiving dinner in 2019. In true Hilton style, she fell fast and hard. "We just had this incredible chemistry," Hilton told People in September 2020. "We had our first date and haven't spent a night apart since. It's pretty amazing." The couple walked down the aisle in November 2021, welcoming their son, Phoenix, in January 2023 and their daughter, London, in November 2023.