Untangling Paris Hilton's Dating History: The Engagements, Breakups, Makeouts and Platonic Old Friends

Eternal love optimist Paris Hilton, never at a loss for company during her going-out days, says she finally feels "home" with boyfriend Carter Reum.

By Natalie Finn 08 Sep, 2020 2:00 PMTags
Related: Meet Paris Hilton's Boyfriend Carter Reum

Paris Hilton is known for a lot of things.

Being timid when it comes to matters of the heart is not one of them.

No matter where you fall on the Paris fan scale, from admiring her business acumen and early mastery of personal branding to wondering what, exactly, it is that she does, there's something endlessly endearing about her lasting love affair with love—a subject she could easily approach with the cynicism of someone who's been dating in the public eye for 20 years, but instead celebrates with the fresh bloom of a thousand roses.

"When we first met, I had no idea of the amazing journey I was about to embark on. My life was always empty, like I was missing something," she wrote on Instagram in tribute to boyfriend Carter Reum on Aug. 29. "But when I met you, I knew you were the one. You've filled my heart with so much love. I believe that everything happens for a reason because everything in my life, all the good and the bad, has led me right to you."

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Paris Hilton's Coachella Looks Through the Years

In that post, Hilton also wished him happy anniversary—a milestone she appears to be marking monthly, calling it their anniversary on July 29, and on April 29.

"You are my fairytale and dream come true," she wrote in June, and days ago she called him "the man who steals my heart, makes my heart flutter, sweeps me off my feet, and puts butterflies in my stomach. I love all our memories and adventures together."

Now that is tackling romance with gusto.

At the same time, as much as she relishes falling hard and fast, she's proven equally adept at not getting carried away when it matters. (As in, at the point where lawyers would have to get involved.)

"I feel like the luckiest girl in the world," she said on The Jenny McCarthy Show last year, about six months after calling off her engagement to Chris Zylka. "Just to feel single and free...I just feel more alive than ever, and I know myself better than ever. I'm just excited."

Agreeing with McCarthy that getting older has its benefits, Hilton added, "I feel so wise."

YouTube Originals

A common refrain, actually, for the former socialite and Simple Life star when she's in between relationships, the hotel heiress always choosing to look on the bright side of a breakup.

But her eternal optimism when it comes to being in love, or not being in love, is just one side of the story. And the 39-year-old DJ, painter and purveyor of fragrances and skincare line ProD.N.A. by Paris Hilton was recently busy rattling people's expectations in the upcoming YouTube Originals documentary This Is Paris, premiering Sept. 14, which she has heralded as an unprecedented look at the real her.

"Obviously, I'm used to being on camera from being on camera for so long," she explained to Jimmy Kimmel Live guest host Nikki Glaser in July. "But I've always been a very naturally shy person. So, I loved just inventing this character and playing that character. And to actually be myself was a completely different experience, but also almost therapeutic in some way where I learned so much about myself that I had no idea of why I am the way I am, and now I understand myself so much more."

Instagram

One of the things she talks about in This Is Paris is having trust issues in relationships, as she's seen setting up a spy-cam in her house and revealing a stockpile of laptops she has acquired because, seemingly every time she has a new boyfriend, he demands access to her computer, or helps himself to it anyway. There was also the time an ex lost his temper and smashed her laptop against the wall. Subsequently, she gets herself a new computer when she starts dating someone.

She's "been betrayed so many times, so she has a tough time trusting people and letting people in," younger sister Nicky Hilton Rothschild says in the film.

So while Paris has been first to admit that she dives into love head first when she does find it, she hasn't exactly had the wild, devil-may-care existence that her erstwhile party girl image tended to suggest.  

Yes, she went out a lot, and there is a museum's worth of photographs to prove it. But just being seen in the company of (and sometimes making out with) the who's who of young male Hollywood didn't necessarily mean something else was going on—or that she wasn't simply having fun, just like the guys she was sharing the kisses with, none of whom ever ended up quite so judged.

"People think I sleep with everyone, but I'm not like that," Hilton told British GQ in 2006. "Kissing is all I do. I'm not having sex for a year. I've decided...I'll kiss, but nothing else."

She explained, "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. I feel good about [putting sex on pause]. I like the way guys get 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."

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

Nevertheless, spotting Hilton out in the wild back in those glitter-dusted days was a full-time job—and she was well aware that people couldn't get enough of her exploits. 

And if she does decide to get married one of these days (a source told Us Weekly in January that a "proposal and wedding could happen very quickly"), she never has to worry that she didn't make the most of her single life:

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.

Afrojack

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 so far, the entrepreneur she first went public with at a 2020 Golden Globes after-party is fitting the bill.

"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."

In August, her Instagram by then littered with photos, videos and collages featuring them kissing, she wrote: "One day you will kiss someone and know those are the lips you want to kiss forever."

Hilton's also been posting a lot of throwbacks of their snowy trip to Montana's Yellowstone Club during the winter, and they've done a bunch of traveling since—wine country in Napa, the Hamptons, Traverse City, Mich. (known for its National Cherry Festival!)—as well as enjoying the beaches of Malibu closer to home.

And she sounds really, really happy. "You are my reason for me being so happy and feeling like the luckiest girl in the world!" Hilton wrote to Reum a week ago. "I love making you happy and promise to make you smile forever. Love so much handsome! Happy anniversary!"