Paris Hilton's Epic Romantic History: All the Hookups, Breakups & Drama You Forgot About

If the party-girl reality star turned businesswoman and globetrotting DJ does get married one day, she won't have to worry that she missed out on any fun

By Natalie Finn Nov 19, 2018 6:45 PMTags
Paris Hilton, Chris Zylka Tommaso Boddi/Getty Images for Maddox Gallery

Chris Zylka wasn't the one after all.

Paris Hilton has called off her engagement, less than a year after The Leftovers actor popped the question on a mountaintop in Aspen with a $2 million diamond ring that took up the entire bottom half of her finger.

The pair had postponed their wedding date—Paris had dreamed of tying the knot on 11-11—supposedly due to the bride-to-be's busy schedule that hadn't left her with enough time to plan her nuptials to the level she envisions for her big day. A spring wedding was looking more likely, a source said.

However, we're told that at a gallery event in Los Angeles last month, she and Zylka were barely acting like a couple. "It was just awkward," another source recalls to E! News. "No affection."

Paris Hilton and Chris Zylka's Cutest Pics

Thwarted plans aside, the hotel heiress, reality-TV star and party girl turned enterprising businesswoman and globetrotting DJ has come a long way since her days as Hollywood's most devoted scenester. Sister Nicky Hilton had settled down and Paris too had her sights set on starting a family of her own.

"I can't wait to have a baby," she told E! News. "I'm gonna be the best mom."

Hilton told People after she got engaged to Zylka, "Ever since our first date I knew there was something special about him. I have never in my life met a man so loyal, dedicated, and loving. I knew right from the start that I wanted to be with him forever."

Iconic#All/Getty Images

Her enthusiasm can be infectious.

But this isn't the first broken engagement for Hilton, whose soul mate to date has been love itself.

"I am so happy now," she told London's ES Magazine in the spring of 2017, insisting she didn't miss those crazy days. "When you are young and growing up you find out who you are when you live life. I want to be a good influence on other girls to inspire them to be businesswomen and show, like, girl power." About Zylka, she added, "I'm so in love. He's the man of my life. We're best friends."

If she does walk down the aisle one day, Hilton can rest assured that she packed a lot of living into her bachelorette days, some of which she spent weeding out the guys who seemed like Mr. Right but proved not to be the one, while other times she had us convinced that the party that seemed to always be raging around her circa 2006 would never end.

Stars' Engagement Rings

Still other times she seemed to cycle through men as if they were handbags, enjoying herself at every turn while not wanting to get tied down. Because if dudes could do that, why not the girls?  And then, of course, there were the endless rumors that linked her to every guy she was ever photographed with or even at the same party as, even when she was just hanging out with her friends.

Hilton, who admittedly has had her escapades, was savvy enough at an early age to know that she couldn't go out without making headlines, nor did she necessarily want to, but she tried to keep a lid on whatever stories she could. In 2000, for instance, the then-19-year-old adamantly denied to Vanity Fair that she and Leonardo DiCaprio were anything more than friends.

"We hang out at parties. He's a nice guy, but as far as the story that I..." Paris said, before her mother, Kathy Hilton, interjected, "Did you see the story? I mean, a full page in the National Enquirer? We were harassed! We had camera crews waiting downstairs [outside their NYC home] because it said that [DiCaprio] would come up to the apartment and whatever. The paparazzi stand outside Paris's house in L.A.—they waited for her at the airport!"

"People think I'm just this party girl," Paris added. "Well, I'm not like that. I don't just go to parties. I wake up in the morning and go to auditions. I was going to go to college, but then I decided to take a year off. [My parents] were mad."

Paris Hilton's Traumatic Trip to Jail Was 10 Years Ago: How She Revamped Her Life After the Celebutantes Gone Wild Era

But she did go to a lot of parties, and she would turn 21 and start going to even more. In the September 2006 issue of British GQ, Hilton sought to dispel the assumptions that, just because she enjoyed makeout sessions at the clubs didn't mean those kisses were leading to anything more.

"People think I sleep with everyone, but I'm not like that," Hilton said. "Kissing is all I do. I'm not having sex for a year. I've decided...I'll kiss, but nothing else."

Her DUI arrest and eventual trip to jail in 2007 for violating probation served as a wake-up call, but even then... the party wasn't over until it was over.

With those glitter-dusted days long behind her now, Hilton is in an entirely different place in every respect than she was 11 years ago. But a trip down memory lane reminds us of just how wild the mid-'00s really were. 

Edward Furlong

Young Hollywood at its wildest. The Terminator 2: Judgment Day star was dating Hilton during some of his more memorable nightlife exploits.

"No, we're not married, but he is my boyfriend. We've been going steady together for about a month," Hilton told the New York Post in September 2000.

Rick Salomon

Forever linked for posterity thanks to their 2001 sex tape, eventually marketed by Salomon and his brother in 2004 as 1 Night in Paris. Hilton knew in hindsight that it wasn't one of her better choices. While the grainy video added to her oh-so-'00s pop culture cachet, she was aware that her image would never fully recover, or at least not for years, till her generation really grew up.

"I always looked up to Princess Diana and all these women, and now I could never be like that," Paris said in a 2009 MTV documentary Paris, Not France. "I want to have a family. I want to be normal. I want to be happy."

Jason Shaw

Paris was barely 21 when she dated the model, who's eight years older, in 2002. They stayed friendly though, and sparked rekindling rumors when they were spotted together in 2010.

"Paris has always loved Jason and cared about him deeply," a source told E! News. "But when they were together she was just a kid and not ready for such a commitment."

Deryck Whibley

They shared some kisses on the party circuit while Hilton was on The Simple Life in 2003, but nothing so serious that it prevented Paris from palling around with the future (and now ex) Mrs. Whibley Avril Lavigne down the road.

"Uh, no," Whibley told Livewire in 2004 when asked if he still talked to Hilton. "If I saw her, I would, but I don't talk to her on the phone or anything."

Simon Rex

The MTV VJ and actor soon to be known as Dirt Nasty was a member of Hilton's party circle in its prime, so of course the rumor that they were more than friends followed.

They stayed close enough that Hilton was among the celebs who made a cameo on his web series Rex, and her appearance was considered darn funny. 

"People think Paris is a ditzy blond, and I don't want to blow it for her, but she plays it really well," Rex told Mediaite in 2009. "She knows exactly what she's doing. She's actually a pretty smart person. She's very cognizant of what she's doing, and she kind of plays that role, so people think she's some airhead but she's really not. She's definitely parlayed what she's been given into something bigger and better. She said something interesting to me once: she said, 'I just tell everyone what they want to hear, and I do what I want to do.'"

Fred Durst

The Limp Bizkit frontman was fighting the ladies off with a stick in 2004. But down the road, when Hilton came up during an interview years later, the notoriously loose-lipped "Nookie" singer didn't kiss and tell.

Jamie Kennedy

Hilton was rumored to be dating the Scream star, but they were friends for years.

Joe Francis

The Girls Gone Wild founder briefly dated Hilton during his own wilder days in 2003 and he later called her "indomitable" but a "handful," telling People, "You can't date Paris seriously without drama."

Nick Carter

The socialite and the Backstreet Boy were no Britney and Justin, at least as far as "aw, remember how great that was?" rosy nostalgia goes. After seven months of dating, during which the Salomon sex tape came out, they broke up in July 2004, with Carter telling People theirs was a relationship "based on distrust."

The aftermath goes like this: They split up July 22. On July 26 Hilton was out partying with Nick's brother Aaron Carter, Bijou Phillips and younger sister Nicky Hilton, when they ran into Nick in Hollywood. According to Nick's lawyer, Paris went home with him; the next morning he drove her to a meeting. The next time Paris' photo was taken, on July 28, 2004, she had bruises on her face. Carter denied having anything to do with it, telling People, "I'll tell you one thing: I didn't touch her. I'm not that kind of guy. I would never do that."

In 2006, Carter unloaded on Ryan Seacrest's KIIS-FM show, claiming he hooked up with Ashlee Simpson to get back at Hilton for cheating on him with her House of Wax co-star Chad Michael Murray, who was married to Sophia Bush at the time. He didn't mean to hurt Simpson, he said, but "Paris and her are two different people and Ashlee is a good person from what I know...and I'm not saying that Paris is a bad person, but I'm saying she's got to work her problems out."

Chad Michael Murray

Well, if you believe Nick Carter.

Paris Latsis

Remember "Paris and Paris"?! Hilton dated the Greek shipping heir for eight months before he proposed in May 2005, reportedly presenting her with 15 rings to choose from.

"I'm so in love and grateful to have found such an honest and loyal person," Hilton gushed to Us Weekly. "I feel like we were meant to be, and I'm happy to have found someone to spend the rest of my life with."

They ended their engagement in September 2005, seemingly just days after Hilton purchased a piece of art at Kitson that actually featured her and her fiancé, surrounded by angels that held a banner reading "True Love." "I'm sad to announce that I've called off my engagement," Hilton said in a statement. "Over the last couple months [aka, the entire course of their engagement], I've realized that this is the right decision for me. We remain best of friends, and I'll always love him. I hope people will respect my privacy during this emotional time."

Latsis said in his own statement, "Right now is a very tough time for me. I love Paris very much. This was the best experience of my life."

Stavros Niarchos III

Literally hours after confirming the breakup with Latsis, Hilton was out partying with a group that included Niarchos, another Greek shipping heir and the former boyfriend of Mary-Kate Olsen, who didn't take the new pairing particularly well.

"[Paris and I] always only had nice things to say about each other," Olsen told W in December 2005. "Now I guess you can tell we're not talking."

Hilton and Niarchos would date off and on before finally calling it quits in March 2007, with a friend of Paris' telling E! News, "she's been over Stavros for a while."

Josh Henderson

When Paris broke up with Stavros for good, there were already rumblings about her and the Desperate Housewives actor, who used to date Ashlee Simpson. Henderson was spotted out and about with Hilton for a few months in early 2007, before her sojourn to jail that June.

"I haven't talked to [Paris] in a long time," Henderson told E! News when we caught up with him in 2009. "But she's always doing well."

Tyler Atkins

After jail, life really was a beach, especially while hanging with the Australian surfer (and future winner of The Amazing Race Australia in 2011) in Malibu in July 2007.

"She is a really smart, amazing girl, and we share similar interests," Atkins told Who.com of their days in the sun. "We have been hanging out at the beach, talking about fashion, and it has been lots of fun. She's a cool girl, and we're having a really great time enjoying each other's company."

Adrian Grenier

You know what else reached the height of its popularity in the mid-'00s? Entourage. But Grenier, who was spotted in Paris' friend zone in 2006 and 2007, was busy getting inspired. In Teenage Paparazzo, the 2010 documentary he directed, Grenier sits Hilton down to explain the story of Narcissus and the origins of the term "narcissism" to her.

"There is serendipity in documentary film-making," he told Popcorn Biz, laughing about that scene. "It's just about sewing all of those little gems together and that's what we did."

More recently, in response to a caller into the Watch What Happens Live After Show, Grenier clarified that his relationship with Hilton was always platonic. "In fact, I was hanging out with her because she was a main character in a documentary I made about the paparazzi...She was very kind to let me into her world and see what she goes through...'cause at the time she was the number-one target for the paparazzi."

Benji Madden

Hilton was gaga for the Good Charlotte guitarist when they dated, excited about him and the idea of marrying the twin brother of the partner of her own bestie, Nicole Richie.

"Yeah, they're twins," she told David Letterman in May 2008 about Benji and Joel Madden. "It's actually perfect. We're like sisters and they're twins, so it works out well. Nicole and I would be sisters-in-law. We talk about it. I'm so happy. I'm so in love. I know I want to spend the rest of my life with Benji, my boyfriend. I know I want to be with him forever. If you saw us together, you'd understand. He's my best friend."

Sadly, they broke up that November. "She was just so busy lately and her work and travel schedule made it difficult for them to be together," a source close to Hilton told E! News. "She's really very saddened by the split and wants some time to be alone and really focus on herself right now and her work."

Doug Reinhardt

Paris seemingly fell hard in early 2009 for the baseball player turned sports agent (and familiar face on The Hills), but she ended it six months later, confirming the split to E! News via her publicist. Eventually Doug got the memo.

But sister and BFF Nicky Hilton wasn't a fan, so it would have never worked anyway.

Cy Waits

Her 2010 relationship with the prolific Vegas club manager went off the rails when she was arrested for alleged cocaine possession after he got pulled over in August 2010, resulting in a DUI charge for him—just a week after Waits had held off a would-be intruder at gunpoint till the cops showed up to Hilton's L.A. home. "He's her knight in shining armor," a source told E! News after the incident.

After the arrest, Hilton pleaded guilty to misdemeanor drug possession and obstructing an officer and avoided a felony charge, which could've come with jail time if convicted.

That didn't spell the end for the couple, however. They chugged along until June 2011, after which Hilton told E! News, "Cy is a good guy. We've been friends for years and always will be. I just need some time alone to focus on myself. We speak all the time. I have nothing but great things to say about him."

Todd Phillips

When she was done focusing on herself, Hilton got to know the Hangover director in 2011.


The Dutch DJ-producer was set to produce an EDM album Paris was working on after she signed with Cash Money Records and they started showing up at events, such as the 2012 Grammys, together—so of course they were rumored to be a thing. A thing which ended that May, after Afrojack supposedly pulled the plug because he wasn't looking for anything serious.

In addition to deejaying and recording, "I also spent the last year traveling to different shows around the world with Afrojack," Hilton nonchalantly told E! News in June 2012. "This was a great experience, to watch how he engages the crowd and creates great energy at these parties."

No Afrojack-produced album emerged, however. 

"Oh I've shut that up," he told Digital Spy in March 2014. "That might have come out a bit harsh. I'm still in touch with Paris, but musically we've taken different paths. There was so much bulls--t surrounding everything, because she is who she is. I gave her a shot, but eventually, enough is enough."

River Viiperi

Hilton started dating the Spanish model in 2012 and no one knew they had broken up until she was spotted kissing someone else.

Josh Upshaw

Clubs are so 2000-and-late but it's never a bad time to kiss a Ralph Lauren model on the beach in Malibu. July 2014 works.

Thomas Gross

Not long after she told DuJour, "I really don't have time for a boyfriend" and, regardless, she'd "rather be single" than date guys in Los Angeles, her international ways led her to meet Switzerland-based Austrian businessman Thomas Gross in 2015, reportedly at the Cannes Film Festival. "I just feel like I'm in a different place in my life. I live in Switzerland now. I'm in love," she told E! News in February 2016. "I don't know, I finally feel like myself. It's exciting. [I'm] genuinely happy."

But though she considered them "soulmates" at the height of their year-long romance, their separately busy lives ultimately drove them apart and they split up in April 2016.

Chris Zylka

"I've never been surer of anything in my life," Hilton told E! News in March 2017 about the Leftovers actor. "He's so incredible in every way. We've actually been friends for a really long time, like the past six years. We just now started being serious in the past few months and it's really just changed my life in so many ways and brought so much happiness to my life. I feel so safe and he's so special. We're best friends and we're together every minute. I don't know what else I could ask for. He's perfect for me."

Zylka proposed before New Year's while they were skiing in Aspen and she said yes, ringing in 2018 as an engaged woman. "Ever since our first date I knew there was something special about him," Hilton gushed to People afterward. "I have never in my life met a man so loyal, dedicated, and loving. I knew right from the start that I wanted to be with him forever."

Alas, their reported November 2018 wedding date (she dreams of tying the knot on 11-11) came and went and the following month a source confirmed that they had ended their engagement. Zylka wasn't Hilton's forever-guy after all. 

Talking to Cosmopolitan UK toward the end of 2019, she called breaking up with the actor "the best decision I've ever made in my life. I just don't think [he] was the right person and I feel like I'm an incredible woman and I deserve someone so amazing. It just didn't feel right. I've worked way too hard to just give my life to someone. They have to be perfect."

Carter Reum

No pressure, Carter. But the entrepreneur she first went public with at a 2020 Golden Globes after-party totally fit the bill, and Paris announced their engagement on Feb. 17, 2020, her 40th birthday.

"From the moment you walked into my life you changed it in every way," Hilton wrote on Instagram in July. "Every day with you has been a blessing. You have shown me what true love really is. Thank you for all the incredible memories, the late night laughs and the early morning kisses. Thank you for making me feel safe, holding my hand through this life and proving that good men still exist. In you I've found the love of my life, my other half, my partner, and my best friend. Thank you for making me the happiest girl in the world! I'm so excited for our future together! I love you forever and ever."

Moreover, she wrote, wherever they are, "For the two of us, home isn't a place. It's a person. And we're finally home."

Seriously, was anyone having a better time than Paris Hilton?

She did her best to set the record straight, no one able to keep up with all of the guys it was just assumed she'd hooked up with, whether she knew them or not. But when you're young and free, who doesn't want to go out, dance and maybe make out like there's no tomorrow? 

"The reason so many of my relationships don't work is guys are like, 'Hey, what's going on? It's been like four months and I'm only getting a kiss here,'" she also told British GQ back in 2006. "I feel good about [my decision to abstain from sex for awhile]. I like the way guys so crazy when they can't have sex with you. If he can't have you, he stays interested. The moment he has you, he's gone. Unless he is really in love with you."

Though Paris almost always seemed to be in the driver's seat when it came to whom she was spending her time with and for how long, not everyone turned out to be a prince. Several famous guys have paraded through Howard Stern's studio and been less than discreet. There are rumors galore about just how close she got to the likes of frequent party pals such as Cristiano Ronaldo, Jared Leto (they were at least kissing buddies), Kid Rock and others. 

But she also just had tons of friends. When you're everywhere, you inevitably come across practically everyone.

And Hilton has long since figured out how to just live her life without worrying what other people are thinking of her.

"I spend my time working rather than just enjoying myself and being on vacation," she told Harper's Bazaar at the end of 2016. "I am very focused on my business and when you live in that mind frame, you can stay away from the trashy tabloids."

She sounded pretty psyched to marry Zylka, but for not the first time she realized that it wouldn't be right to say "I do" if she wasn't ready.

"What made her strong was despite the million things that hurt her," she captioned an Instagram post Sunday night. "She spoke of nothing but happiness..."

(Originally published Jan. 4, 2018, at 5 a.m. PT)