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A Look Back at Paris Hilton’s Dramatic Dating History (Including Her Four Engagements!)

Paris Hilton is (a) engaged, (b) currently planning a wedding, and (c) 100 percent not pregnant, despite, ahem, rumors you may have heard to the contrary. Yep, the reality star, DJ, socialite, and—some (me) might argue—living legend is making it official with VEEV Spirits cofounder Carter Reum, who she plans to “spend forever with.” Couldn’t be more pumped for these two! And while we wait for their fancy wedding to go down, we’re taking a look back at Paris’s prior relationships that led to her finding her forever soul mate—including three other engagements. And also a very random beef with Nick Carter? Lol.

Carter Reum: January 2020 to NOW

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Paris and Carter fell hard and fast, getting engaged just a few months after dating. Paris announced news of their engagement on Instagram, writing, “My love and I have been together since our first date and for my birthday, he arranged a special trip to tropical paradise. As we walked to dinner along the beach, Carter led us to a cabana adorned with flowers and dropped to one knee. I said yes, yes to forever. There’s no one I’d rather spend forever with.”

Chris Zylka: February 2017 to November 2018

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Paris and actor Chris Zykla dated for about a year, and it got super serious for a moment! To the point where they even got engaged, with Chris popping the question during a ski vacation. But alas, the couple called off said engagement in November 2018 and a source told Us Weekly, “She broke up with him a couple of weeks ago. She has been out of the country in Dubai and Australia. Paris realized that it wasn’t meant to be and he wasn’t right for her. There were some problems along the way. She’s done.”

Thomas Gross: Circa 2015 to April 2016

Paris and Swiss millionaire Thomas Gross dated for about a year after meeting at Cannes in 2015 but broke things off in April 2016. “They are both friends and remain close, but with their busy work schedules and the long distance, it just got too difficult,” a source told Life & Style, adding that “they remain close friends and care for each other but work and the distance just got in the way. She will be back in Ibiza for her DJ residency all summer and he has to be in Switzerland for his work—it’s an impossible situation.”

There aren’t any readily available pics of Paris and Thomas at events together, which actually makes sense considering Paris told Closer this in November 2015: “He’s very private, so he’d never want cameras following us around.”

River Viiperi: 2012 to 2014

cannes, france may 18 model river viiperi and paris hilton attend the zero theorem party hosted by terry gilliam the 66th annual cannes film festival at torch at vegaluna beach club on may 18, 2013 in cannes, france photo by tiffany rosegetty images for torch

Tiffany RoseGetty Images

Paris and model River Viiperi dated for about two years, and she confirmed rumors of their split when she was spotted kissing a ~mystery man~ in front of paps in Malibu. Around the same time, River posted a woeful and since-deleted musing to Insta that read:

“At some point you will realize that you have done too much for someone or something, that the only next possible step to do is to stop. Leave them alone. Walk away. It’s not like you’re giving up, and it’s not like you shouldn’t try. It’s just that you have to draw the line of determination from desperation. What is truly yours would eventually be yours, and what is not, no matter how hard you try, will never be.”

Subtle!

Cy Waits: Circa 2010 to June 2011

beverly hills, ca january 16 paris hilton l and cy waits attend nbcuniversalfocus features golden globes viewing and after party sponsored by chrysler held at the beverly hilton hotel on january 16, 2011 in beverly hills, california photo by christopher polkgetty images for nbcuniversal

Christopher PolkGetty Images

This one was kinda messy! Club owner Cy Waits appeared on Paris’s show The World According to Paris, and apparently he didn’t love how he was portrayed. By the time they broke up, Cy wasn’t shy about dissing his ex in the press, telling People, “I don’t want to speak for Paris, but this breakup is something I knew for a number of months needed to happen—and we finally saw eye to eye. I need to get back to focusing on my career. In my next relationship, I expect honesty, strong values, true communication, commitment, mutual trust, and respect, something I didn’t necessarily have recently. At the end of the day, I want my partner and I to have the same ethics.”

Doug Reinhardt: Circa 2009 to April 2010

cannes, france may 20 paris hilton and doug reinhardt attend the inglourious basterds premiere held at the palais des festivals during the 62nd international cannes film festival on may 20, 2009 in cannes, france photo by michel dufourwireimage

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Paris and The Hills star Doug Reinhardt dated for about a year and also had a super-messy split. Like, she went in during an interview with Us Weekly, saying, “I am, like, so past that—I don’t even care! I don’t even remember that time in my life. I am over it! I just realized that I’m better off without him. So I ended it because I deserve something much better! He wasn’t right for me and I will eventually find somebody who loves me for who I am.”

Benji Madden: March 2008 to November 2008

hollywood april 22 musician benji madden l and paris hilton pose during the glow in the dark tour 2008 party ignited by absolute 100 held at goa on april 22, 2008 in hollywood, california photo by michael caulfieldwireimage

Michael CaulfieldGetty Images

No drama here! Benji and Paris were short and sweet, and when they broke up, a source told People, “She is saddened by the breakup but they’re just too different and they wanted different things in life. He was loyal and sweet but it was time to take a break.”

Stavros Niarchos: September 2005 to May 2006

paris hilton and stavros niarchos photo by john shearerwireimage for teen vogue

John ShearerGetty Images

Paris was spotted with Greek shipping heir Stavros Niarchos days after she split with Paris Kassidokostas-Latsis (we’ll get to him in a sec), and they dated on and off for about a year. Paris’s rep confirmed their breakup in early May, saying, “I confirm that she’s split with him. They are no longer a couple. I don’t know the exact day they split.”

Paris Kassidokostas-Latsis: December 2004 to September 2005

paris latsis and paris hilton during paris hilton and paris latsis sighting at the kabaret club in london june 27, 2005 at the kabaret club in london, great britain photo by niki nikolovafilmmagic

Niki NikolovaGetty Images

Paris and her name twin dated for just about a year, and their ~thing~ can best be described as a whirlwind. Like, they got engaged after just eight months. Both of them seemed more than happy to talk to the press about their split, with Paris (the guy) telling People, “Right now is a very tough time for me. I love Paris very much. This was the best experience of my life.” Meanwhile, Paris (the gal) said, “I will always love him. He treated me like a princess the entire time. I love how he’s handling this like a gentleman. I really respect that.”

Nick Carter: January 2004 to July 2004

paris hilton and nick carter during ps2 estate day 3 6th annual p diddy white party at ps2 estate in bridgehampton, new york, united states photo by shareif ziyadatfilmmagic

Shareif ZiyadatGetty Images

Yep, Paris dated Backstreet Boys’ Nick Carter for just seven months! And he, uh, said some pretty unflattering things about their time together in his 2013 autobiography, writing, “Paris was the worst person in the world for me to hook up with. [She] fed my worst impulses as far as partying.”

FYI, Paris shot back, “I don’t believe I was a negative influence on Nick. We dated for a very short period of time almost 10 years ago and when we met, he was already a successful pop star, I’m pretty sure that was the only thing influencing him at the time. I’m glad he got help for his problems and wish him all the best.”

Deryck Whibley: Circa 2003

deryck whibley and paris hilton at the the loews hotel in miami beach, florida photo by rodrigo varelawireimage

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It was short, it was sweet, and barely anything was written about it because truly, what even was the internet back then?

Jason Shaw: 2002 to 2003

jason shaw paris hilton during 44th grammy awards andre harrells party at the gq lounge at sunset room gq lounge in hollywood, california, united states photo by steve jenningswireimage

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Paris and model Jason Shaw were engaged before online tabloids were really a thing, and not much is known about their relationship—other than that they stayed friends and hung out in 2010. A source told E! News at the time, “Paris has always loved Jason and cared about him deeply. But when they were together, she was just a kid and not ready for such a commitment.”

Rick Salomon: Circa 2001

exclusive, premium rates apply rick salomon photo by barry kingwireimage

Barry KingGetty Images

Paris and Rick dated for a couple of years, and he completely destroyed her trust by leaking their sex tape. “I just felt so betrayed,” Paris told CNN years later. “This was not some random guy; this was someone I was with for a few years. I thought I did [love] him, and I can’t believe that he would do something like that to me. It’s something that changed my life forever.”

Ugh. So glad Paris has found her happily-ever-after after going through all this! Can’t wait to watch her wedding prep play out on her upcoming show, Paris in Love (which is filming rn!).

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