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Paris Hilton is engaged and looking happier than ever.

Not that we haven't seen her looking happier than ever, or engaged, before—but 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.

In 2000, for instance, the then-19-year-old adamantly denied to that she and Leonardo Di Capriowere anything more than friends."We hang out at parties. We had camera crews waiting downstairs [outside their NYC home] because it said that [Di Caprio] would come up to the apartment and whatever. Whibley Avril Lavigne down the road."Uh, no," Whibley told Livewire in 2004 when asked if he still talked to Hilton.

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? "If I saw her, I would, but I don't talk to her on the phone or anything." Gustavo Caballero/Getty Images 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.

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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. And when you're everywhere, you inevitably come across practically everyone. Paris Hilton is planning on marrying Chris Zylka and, when they say "I do," it'll be the end of an era."I spend my time working rather than just enjoying myself and being on vacation," she told at the end of 2016.

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. I was going to go to college, but then I decided to take a year off. But a trip down memory lane reminds us of just how wild the mid-'00s really were. Hilton knew in hindsight that it wasn't one of her better choices."We have been hanging out at the beach, talking about fashion, and it has been lots of fun. He's my best friend."Sadly, they broke up that November. But sister and BFF Nicky Hilton wasn't a fan, so it would have never worked anyway. "He's her knight in shining armor," a source told E! 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. They chugged along until June 2011, after which Hilton told E! "Oh I've shut that up," he told Digital Spy in March 2014. I'm still in touch with Paris, but musically we've taken different paths. Axelle/Bauer-Griffin/Film Magic "I've never been surer of anything in my life," Hilton told E! 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. We're best friends and we're together every minute. 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.She's a cool girl, and we're having a really great time enjoying each other's company." , 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. I know I want to spend the rest of my life with Benji, my boyfriend. "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! "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." ), but she ended it six months later, confirming the split to E! Courtesy of David Becker/Wire Image 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. There was so much bulls--t surrounding everything, because she is who she is. But when you're young and free, who doesn't want to go out, dance and maybe make out like there's no tomorrow?Carter denied having anything to do with it, telling , "I'll tell you one thing: I didn't touch her. 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 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..I'm not saying that Paris is a bad person, but I'm saying she's got to work her problems out." Jon Furniss/Wire Image Remember "Paris and Paris"?!

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