Though she’s found her prince charming in Carter Ream and is now mom to a child with the millionaire entrepreneur, Paris Hilton’s road to wedded bliss hasn’t been an easy one. From a sex tape scandal, bitter break-ups, fleeting celebrity romances and a total of four engagements, DailyMail.com takes a look at the very extensive relationship history of the 41-year-old hotel heiress…

Chris Zylka – 2017-2018

Paris’ most recent proposal before finding love with Carter was with HBO actor Chris Zylka. The pair began dating in 2017, and he proposed a year later in January 2018 on an Aspen, Colorado ski trip. Paris said of their romance at the time: ‘My best friend and soul mate. Perfect for me in every way. They will break up after a few months.

The X-Factor: Paris and ex-fiancé Chris Zylka in 2018

Thomas Gross – 2016

The Simple Life star and businessman Thomas Gross — who is worth more than $200 million — dated for a year before separating in April 2016. The pair met at the Cannes Film Festival in 2015, and were said to hit it off immediately. She named him her ‘soulmate’ in an Instagram caption at the time and even had him as her date to sister Nicky Hilton’s wedding, but it was not to be.

Viper River – 2012 – 2014

This Spanish model Rivera Viperi and Paris dated for two years – and the pair were often spotted packing on the PDA while partying. But the hotel heiress had moved on in 2014, and confirmed their breakup by kissing a mystery man on the beach in Malibu.

Model ex: Paris and the River Viperin 2014

Model ex: Paris and the River Viperin 2014

Afrojack – 2012

Paris was linked to Afrojack in 2012. Her rep denied reports that she was dumped by the DJ, instead saying they are “best friends” and “love and support each other very much.”

Cy Vet – 2010-2011

The reality star dated nightclub organizer Cy Waite for about a year before parting ways in June 2011. Things went downhill for the couple after they were arrested in Las Vegas, with Cy being busted for driving under the influence. He lost his job as head of nightclub operations for the Wynn and Encore in Vegas.

PDA: The heiress as seen with Doug Reinhardt in 2009

PDA: The heiress as seen with Doug Reinhardt in 2009

Doug Reinhardt – 2009–2010

There was no love lost between Paris and The Hills star Doug Reinhardt. After a messy split, she told Us Weekly: ‘I’m, like, so past – I don’t even care! I don’t even remember that time in my life. I am on it! I just realized that I am better off without him. That’s why I ended it because I deserved something better! He was not right for me and finally I will find someone who loves me for who I am.

Benji Madden – 2008

Before marrying Cameron Diaz, Paris Hilton and Benji Madden dated for nine months. However, this was not to be as she split from the Good Charlotte guitarist in November 2008. A source said at the time, ‘She is saddened by the breakup but they are very different and they want different things in life.’ ‘He was loyal and lovely but now it was time to take a break.’

Rocker: The star is pictured with Benji Madden in 2008

Rocker: The star is pictured with Benji Madden in 2008

Stavros Niarchos – 2006

Stavros Niarchos, the son of a Greek billionaire shipping tycoon, dated Paris around 2006 before ditching her a year later. Prior to Paris, Niarchos was linked to Mary-Kate Olsen. The pair vow to remain friends.

Paris Lattice – 2004–2005

Paris almost married her namesake Paris Kasidokostas-Latis, a Greek socialite and shipping heir. They started dating in December 2004 and got engaged eight months later. But the couple had called things off by September the following year. She famously complained that her 24-carat diamond—reportedly worth $4.7 million—was too heavy on her finger.

Selfie pioneer: Paris takes picture with Stavros Niarchos

Selfie pioneer: Paris takes picture with Stavros Niarchos

Currency: Paris and Paris Lattice in 2005

Currency: Paris and Paris Lattice in 2005

Nick Carter – 2004

The socialite and Backstreet Boys singer Nick were an item for seven months before finally splitting in July 2004. She later said some unkind things about Paris in an autobiography, writing: ‘Paris was the worst person in the world for me to hook up with. [She] As far as partying goes, I fed my worst impulses.’ Paris replied: ‘I don’t believe I had any negative influence on Nick… I’m glad he got help for his problems and I wish him the best.’

Derrick Whibley – 2003

Sum 41 frontman Derrick Wibbly and Paris Hilton were engaged for a few months in 2003. Although they were spotted kissing on the party circuit in Los Angeles at the time, things quickly fizzled out between the pair.

Pop Star: Paris with Nick Carter from the Backstreet Boys in 2004

Punk: Some 41 stars with frontman Derrick Whibley

Pop star rivals: Paris has dated both Nick Carter from the Backstreet Boys and Sum 41 frontman Derrick Wibbly

First big love: Paris and her ex-fiancé, model Jason Shaw, in 2002

First big love: Paris and her ex-fiancé, model Jason Shaw, in 2002

Jason Shaw – 2002

In 2002, just before she turned 21, the Hilton heiress was first engaged to model Jason Shaw, but they split in 2003. They later reconnected in 2010, although they appeared to be just friends. ‘I love her very much. We’re very close and I’ve known him for a very long time,’ she told Ellen DeGeneres at the time.

Rick Salomon – 2001

Arguably one of her most famous exes, Paris and Rick’s relationship hit the headlines when a poker player leaked a sex tape of the two after they split in 2004. Paris later said she felt “very betrayed” and recently claimed the whole experience left her with PTSD. ‘It was my first real relationship. eighteen. I loved him so much and I wanted to make him happy,’ she said in her recent doc This Is Paris. ‘ And I remember him pulling the camera. And he was putting this kind of pressure on me. It was like being raped electronically.

Edward Furlong – 2000

Paris confirmed her romance with the Terminator 2: Judgment Day star after rumors of an engagement and wedding. ‘No, we are not married, but he is my boyfriend. We’ve been moving in together for about a month,’ she informed the New York Post in September 2000.

Notorious: Paris is seen circa 2001 with Rick Salomon, with whom she made the infamous sex tape

Notorious: Paris is seen circa 2001 with Rick Salomon, with whom she made the infamous sex tape

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