From Too Hot To Not: Paris Hilton And Chris Zylka's Relationship History

Paris Hilton’s history of romances and relationships may be one for the record books, having been connected to so many rich and good-looking men. When Hilton met and fell for actor, model and artist Chris Zylka in 2016, it seemed like The Leftovers star might finally be the man to land the hard-to-get heiress and Simple Life star. The relationship felt even more like a sure thing when Zylka popped the question with a $2 million engagement ring.

MORE: It’s Over! Paris Hilton & Fiancé Chris Zylka Allegedly Split After Ritzy Engagement

Zylka wouldn’t be the first man to fall for Hilton and have his heart crushed in the bargain. Before Zylka, the heiress and DJ was previously linked to model Jason Shaw and shipping heir Paris Latsis without marrying either one of them. Three would not be the celebutante’s lucky number, though, as less than a year after saying “yes” to Zylka, the couple’s romance and the relationship were both officially over.

More: Paris Hilton Moves On With Handsome Entrepreneur 1 Year After Breaking Off Engagement To Chris Zylka

If you want to know more about how this romance became so hot before turning cold almost just as fast, check out RadarOnline’s gallery below!

Hilton and Zylka first met while attending an Oscar party at Chateau Marmont. In 2017, the heiress told Galore about that fateful meeting saying, “as soon as he walked through the door, we looked at one another; we’re both shy so it took a while, but by the end of the night we couldn’t stop laughing and flirting." They then “flirted for years and years” over social media, maintaining that flirty relationship while dating other people. Hilton was in a relationship with businessman Thomas Gross in 2015 and 2016 while Zylka was engaged to model Hanna Beth, that engagement ending in a “nasty online feud.”

There are conflicting stories of how they finally decided to date, but Hilton revealed to Page Six in 2017 that Hilton’s brother Barron helped get them together, inviting Zylka to his hotel after seeing the actor’s art at Art Basel Miami. That night, Zylka finally got the courage to ask Paris for her number, although they wouldn’t go on an actual date for another year, instead they texted each other for most of 2016.

Not long after their first date, Hilton was already starting to fall head over heels for the actor/model. As she told Galore, “On our first date he came over to my house. We stayed up all night talking and getting to know each other. When we had our first kiss I felt that electric feeling and knew there was something special about him." The two were almost inseparable after that first date, Zylka travelling with Hilton as she continued her busy schedule of DJing and running her product lines.

Things were looking grand for Hilton’s latest relationship as it progressed over the next few months. "I've never been surer of anything in my life," she told E! News. "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."

Apparently Hilton’s feelings were reciprocated as Zylka soon tattooed the name “Paris” on his arm in a Disney font to celebrate their one-year anniversary. “Such a lucky girl! ? My love surprised me & got my name tattooed in #Disney font,” Hilton gushed enthusiastically on Insta, explaining that she was his “most magical place on Earth” and that he had finally found “his fairytale princess.” Does it get any more romantic than that?

In her second cover story with Galore, Hilton was asked about her ideal day with Zylka, to which she responded, “My ideal day would be having a day off from work, sleeping in. Then cooking a big breakfast and hanging out at the house with our pets. Then going to Disneyland to go on all the rides. We are both kids at heart so we love doing things like that."

Hilton told Us Weekly that she felt her latest relationship with Zylka couldn’t be more perfect. "I think we're the only couple that never fights,” she said. “All my friends are like, 'Literally, you guys are the perfect couple. I've never seen you argue.'"

A few months after her engagement, Hilton appeared on Access Hollywood telling the show, “We’re still trying to plan the date. I wanted to do it before the summer, but I have so much work, so I want to do a winter wedding,” plus she “wanted it close to home,” so her whole family can attend. They ended up settling on November 11.

“I can’t wait to have a baby,” Hilton told E! News in July at the launch of her skincare line, “I’m gonna be the best mom.” Sounds like the reality star best known for her partying was really taking her upcoming wedding seriously. Maybe this sentiment came out of spending time as aunt to sister Nicki Hilton Rothschild's two very young kids, Lily and Teddy.

A month later, it didn’t seem like that November wedding date was going to happen. It was delayed because, according to one source, “there was too much to do and between her work and travel schedule, not enough time to do it.” At that point, it looked like it would instead be a spring wedding, but the same source said, "She is dead set on getting married so the wedding will happen. Just not as quickly as she had hoped.”

As the couple prepared for their upcoming nuptials it was revealed that Hilton was paying for the entire wedding including that engagement ring, and apparently, she was not happy about it. A source was quoted as saying, “Most of her friends thought she would realize at some point that she was too good for him.”

In late October, Hilton praised her fiancé to Us Weekly while shopping in Beverly Hills.“ He’s even more beautiful on the inside than the out,” she said. “He’s just such a genuine, good man and an amazing, supportive best friend. He’s everything, and it’s really rare and hard to find—especially in L.A. You can’t trust any of these guys. So it’s nice to finally find someone that I can really trust.”

After the wedding had already been pushed back, Hilton finally cancelled the wedding, and the two went their separate ways. The reason for Hilton’s cold feet? During an appearance on The Talk, the reality star said her heart just wasn’t into what started out as a whirlwind romance. "I've always been obsessed with Disney stories and love stories and I thought it was going to be my happy ending,” she told the ladies on the show. “I just realized after time it wasn't the right decision.”

Someone who knew the couple confirmed this by saying, “The relationship moved really quickly, and she realized he wasn’t right for her. She wishes him well and hopes they can remain friends.”

“I’m really just having my ‘me time',” Hilton said on The Talk with her only other comment on the break-up being a video of herself on Insta, dancing to Ne-Yo’s “Miss Independent.” Cold.

Shortly after their break, there were rumors that Zylka wanted that $2 million engagement ring back, but since Hilton paid for it herself — her net worth is $300 million to Zylka’s mere $4 million — that wasn’t gonna happen. In August 2019, Zylka finally covered up that spur of the moment anniversary tattoo ode to Paris with an intricate design of … a gorilla. Ouch!

Over a year after her break-up with Zylka, Hilton was ready to move on and was seen at a Golden Globes party kissing entrepreneur Carter Reum. By February 2020, Hilton was still having no regrets about how things went down with Zylka, telling Cosmo UK, “It was 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."