Before we were keeping up with the Kardashians, we were all tuned into the lives of Paris Hilton and Nicole Richie.
WATCH BELOW: Paris Hilton Confirms She’s Keeping Her $2 Million Engagement Ring from Ex-Fiancé Chris Zylka.
The socialites-turned-reality-stars became icons of the reality show boom in the early noughties – and it’s safe to say that everyone was obsessed with them.
The paparazzi followed every detail of their lives, from the clubs they frequented to the dozens of boyfriends they went through over the years. Paris was particularly intriguing in this case – as early as 1996, she’d been linked to 54 different men!
While we obviously can’t go through all 54, we’ve whipped up a list of 10 of her most fascinating exes. From actors to models to businessmen, this small sample of Paris Hilton’s ex-boyfriends reveals her diverse – and sometimes unexpected – taste in men.
Carter Reum
Fourth times the charm! For Paris’s 40th birthday she received the best gift of all an engagement ring.
She revealed on Instagram that her partner businessman Carter Reum, 40, popped the question on their private island holiday where they were celebrating the business mogul’s birthday.
The loved-up couple has been together since their first date in 2019, but they have actually known each other for 15 years.
Paris honoured their engagement in an Instagram post to reveal all the details about what went down.
“When you find your soulmate, you don’t just know it. You feel it, gushed the star.
“My love & 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.
“Here’s to Love – the Forever Kind”
Designer Jean Dousset, a descendant of the Cartier family, was the artist behind the engagement ring.
A post on Paris’s website called A Ring Inspired By Paris, says that the design is influenced by “classical and Art Nouveau motifs.”
In a Vogue interview Reum told the magazine that “From our very first date, I was able to get to know the real Paris.
“As people who have seen her documentary and recent advocacy work know, Paris is kind, smart, driven, authentic, and an amazing woman, and I can’t wait to have her as a partner in life.”
Hopefully, this engagement will make it to the altar because her wedding is bound to be a no expense spared fiasco.
Chris Zylka
Paris’ most recent ex-beau was American actor and model Chris Zylka. But the man most famously known for his role as Tom Garvey in HBO’s “The Leftovers” was more than just an ex-boyfriend.
He was also Paris Hilton’s fiancé for 10 months!
The two met in 2010 but didn’t become a couple until 2017. In an interview with Galore, Paris had this to say about their first encounter:
“Chris and I met seven years ago, during an Oscar party being held at the Chateau Marmont. 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.”
Chris started exclusively dating Paris in August 2017. Then, only a year and a half into dating, the couple got engaged! But alas, their engagement was just as short-lived. Before the wedding could even happen and she could call him ‘husband’, they separated in November 2018.
Not too long after she shared a photo of her opulent diamond ring on Instagram, she deleted the post.
Thomas Gross
Before Chris, Paris dated 43-year-old Austrian businessman Thomas Gross.
They first met at Cannes in May 2015, Paris referred to Thomas as her ‘soulmate’ on social media.
She even gushed about him in an interview saying, “He doesn’t like fame, he just wants me. With previous boyfriends, I felt there was always an intention, but with him, I know it’s all about love.”
Sadly, their relationship only lasted for 11 months.
How did they go from soulmates to passengers on the train to Splitsville? Well, they were just too busy for each other, and they couldn’t fit their schedules together.
John Upshaw
Another name on the list of Paris Hilton’s boyfriends is Ralph Lauren model John Upshaw.
He was 22 years old at the time when he and then 33-year-old Paris Hilton started dating, Sometime in 2014, the public was subjected to a full-on steamy make-out session in front of Paris’ beach house in Malibu.
However, their summer fling lasted only until October of the same year.
River Viiperi
Another model-turned-former-partner was Spanish model River Viiperi. Unlike the previously mentioned ex, Paris and River dated from September 2012 to July 2014.
But just like John Upshaw, Paris and Viiperi had a big age gap between them.
Despite this though, Paris found no shame in gushing about marrying River. In a guest appearance on The Wendy Williams Show, Paris said, “I am so in love. I feel so lucky to have met him. He’s one of the kindest, most loyal men I’ve ever met in my entire life, and he treats me like a princess.”
Why does it feel like we heard that one before?
Todd Phillips
Director Todd Phillips is famous for his work on The Hangover and most recently, the Joker movie.
But in between making the two films, Todd had a brief relationship with Paris in July 2011.
Much like her other relationships, there was a big age gap between the two – 10 years to be exact.
And just like her relationship before Todd – with American businessman Cy Waits – it wasn’t long before Paris moved on from the filmmaker.
Afrojack
Her relationship with Afrojack was one of those rare instances where Paris wasn’t dating a model.
The 31-year-old Dutch music producer dated Paris for six months in 2012 while he was producing her second album.
According to Radar Online, DJ Afrojack broke-up with Paris because their relationship moved at a fast pace – “very serious, very fast,” he said, and he admitted he was not ready for that kind of commitment just yet.
According to a source, Afrojack “is on the road practically every day performing in clubs all over the world, and he just isn’t ready to settle down, whereas Paris is.”
Cy Waits
Before Todd Phillips, Paris dated Cy from August 2010 to June 2011.
Just as most of us have gotten used to Paris’ short-lived relationships, Cy found their break-up unsurprising as well.
In an interview with People, Cy said, “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.”
And who can blame him? Their relationship wasn’t exactly a fairytale romance.
The former couple even got arrested for possession of cocaine in Las Vegas.
Cristiano Ronaldo
It may be a shocker to some, but Paris Hilton also dated one of the best football players in the world – Cristiano Ronaldo.
Their encounter was quite brief, and the two were only spotted twice in nightclubs in June 2000.
In an interview with The Mirror, Paris only had this to say about Cristiano: “We’re getting to know each other and I have to leave it at that.”
But neither their relationship nor the friendship lasted long.
Reports said that they broke-up because Paris thought he was a “sissy.”
Coming from Paris, that’s a solid burn.
Doug Reinhardt
Paris’ thing for athletes didn’t stop at Ronaldo.
From February 2009 to May 2010, Paris dated 33-year-old American baseball player, sports agent, and TV star Doug Reinhardt.
Before their on-and-off-and-on relationship ended, Paris thought she and Doug were endgame.
In an interview with E! Online, she told them that Dough would be her husband and that she’s “really in love and really happy.”
We guess he didn’t end up being quite the catch she thought he was.
Jared Leto
Here’s an ex-BF that might come as a shock. Did you know that Paris Hilton briefly had a thing for Thirty Seconds to Mars’ lead vocalist, Jared Leto?
The two were spotted making out at a Sundance party in 2008.
Briefly after, it was confirmed that the pair were dating.
But like all good things (and all of her relationships), Paris and Jared’s fling had to come to an end too.
