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As Paris Hilton prepares for marriage, look back at her failed relationships and bitter romances

Paris Hilton is officially a married woman, after tying the knot to her new husband, Carter Milliken Reum, in a glamorous ceremony at her family’s sprawling Bel Air estate. 

But while the 40-year-old heiress has only just said ‘I do’ for the very first time, she has come close to walking down the aisle on several occasions in the past, having been engaged three other times over the past 20 years – only for those relationships to end before she made it to the altar. 

Paris’ road to wedded bliss has certainly been rocky; before she began dating Carter in November 2019 after the pair enjoyed a 15-year friendship, the socialite and reality star had more than a dozen public relationships, several of which were blighted by scandal and heartbreaks. 

The daughter of Kathy and Richard Hilton announced her engagement to Carter on February 17, revealing that he popped the question four days earlier, on her 40th birthday, while the pair were enjoying a romantic vacation on a private island. 

‘When you find your soulmate, you don’t just know it. You feel it,’ the blonde beauty gushed on Instagram while sharing the happy news – and revealing a sneak peek at the stunning $2 million ring he proposed with. 

‘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.’   

As Paris prepares for ‘forever’ with her new husband, FEMAIL looks back at her other 14 partners from the last two decades, revealing where the romances went wrong – and why none of her other beaus ever made it to the altar…

As Paris Hilton gets ready to marry her boyfriend of two years, Carter Milliken Reum, we decided to take a look back at her many failed relationships and bitter romances

On February 17, 2021, Carter - an author, entrepreneur, and venture capitalist, proposed to Paris while they were vacationing on a private island

On February 17, 2021, Carter – an author, entrepreneur, and venture capitalist, proposed to Paris while they were vacationing on a private island

CHRIS ZYLKA – 2017-2018

Paris first met Chris Zylka all the way back in 2010, but it wasn’t until her brother set them up in 2017 that they finally started dating. 

‘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 socialite recalled to Galore about the first time they met. 

Paris told E! News a few months into their relationship that she had ‘never been surer of anything in her life.’ And on their one-year anniversary, Chris got the reality star’s name tattooed on his arm.

Before Carter, Paris was in a relationship with Chris Zylka, whom she started dating in 2017 after her brother set them up

Before Carter, Paris was in a relationship with Chris Zylka, whom she started dating in 2017 after her brother set them up

It definitely seemed like they were as happy as could be together, and in January 2018, the actor, who is most known for his roles in The Amazing Spider-Man, Zeke and Luther, and more, popped the question during a ski trip at Aspen, Colorado with a $2 million 20-carat pear-shaped engagement ring. 

But in November of the same year, they shocked the world when they called off their engagement and went their separate ways. 

Bling thing: Chris proposed in Aspen in January 2018, giving Paris a $2 million 20-carat pear-shaped diamond

Bling thing: Chris proposed in Aspen in January 2018, giving Paris a $2 million 20-carat pear-shaped diamond

As for why they split, Paris later admitted on The Talk, ‘I’ve always been obsessed with Disney stories and love stories and I thought it was going to be my happy ending, and I just realized after time it wasn’t the right decision.

‘But I wish him the best and one day I would love to get married and have children, but for right now I’m just focused on myself and my work.’   

The New York Post reported in 2018 that Chris had asked Paris to return her diamond engagement ring after their breakup, but she refused because he didn’t pay for it. 

A source said the 20-carat stunner was given to her for free by a friend of hers, celebrity jeweler Michael Greene.

Chris, 36, is four years younger than Paris, but their split wasn’t his first broken engagement. He had previously proposed to model and designer Hannah Beth in April 2014. They called off their wedding nearly a year later in March 2015.

THOMAS GROSS – 2015-2016

Paris met Austrian businessman Thomas Gross at the Cannes Film Festival in May 2015, and they quickly became inseparable. 

While there is not much known about the 45-year-old based in Switzerland, they had at least one thing in common: money. 

Thomas, whose first name is actually Hans, reportedly made his fortune as the founder of the sports data company RunningBall. He sold the business to PerformGroup for $150 million in 2012. 

A month after he met Paris, they were photographed kissing on his yacht, Galaxy, which costs a reported $25 million.   

Paris started dating Thomas Gross after they met at the Cannes Film Festival in May 2015. Paris called the businessman her 'soulmate' in an interview two months later

Paris started dating Thomas Gross after they met at the Cannes Film Festival in May 2015. Paris called the businessman her ‘soulmate’ in an interview two months later

She also took him as her date to her sister, Nicky Hilton's wedding. But in April 2016, sources confirmed to Us Weekly that they had split

She also took him as her date to her sister, Nicky Hilton’s wedding. But in April 2016, sources confirmed to Us Weekly that they had split

Paris called Thomas her ‘soulmate’ on Instagram, as well as in an interviews. 

‘Thomas is my soulmate. I’ve never been happier. He doesn’t like fame, he just wants me,’ she told Closer. ‘With previous boyfriends I felt there was always an intention, but with him I know it’s all about love.’

The socialite quickly acclimated to life in Switzerland, where she moved to be closer to Thomas.  

‘I just feel like I’m in a different place in my life. I live in Switzerland now. I’m in love,’ she told E! News in February 2016. ‘I don’t know, I finally feel like myself. It’s exciting. [I’m] genuinely happy.’

She even took him as her date to her sister Nicky Hilton’s wedding to James Rothschild, but in April 2016, sources confirmed to Us Weekly that they had split.

RIVER VIIPERI – 2012-2014  

Paris dated Spanish model River Viiperi from 2012 to 2014, and they definitely weren’t afraid to show off their love throughout their two-year relationship. 

The businesswoman couldn’t get enough of her beau, who was 11 years young. They were constantly spotted packing on the PDA at various parties and events.

‘We just love to sit in the corner and make out and dance. When I’m in the club with him, it’s like no one else in the room exists – it’s just us two with each other! It’s romantic,’ Paris told Life & Style in February 2014.

She also gushed about him on The Wendy Williams Show, saying, ‘I am so in love. I feel so lucky to have met [River]. He’s one of the kindest, most loyal men I’ve ever met in my entire life, and he treats me like a princess.’

Paris dated River Viiperi from 2012 to 2014, and throughout their two-year relationship, they were constantly spotted packing on the PDA at various parties and events

Paris dated River Viiperi from 2012 to 2014, and throughout their two-year relationship, they were constantly spotted packing on the PDA at various parties and events

It's unclear when they broke up, but the star confirmed that they had ended their relationship when she was spotted kissing a mystery man on the beach in Malibu, California, in July 2014

It’s unclear when they broke up, but the star confirmed that they had ended their relationship when she was spotted kissing a mystery man on the beach in Malibu, California, in July 2014

In October 2012, TMZ reported that River was arrested for misdemeanor battery while he and Paris were at a Las Vegas nightclub. The alleged victim claimed River punched him after his girlfriend made out with Paris. 

It’s unclear when they broke up or what went wrong in the end, but the star confirmed that they had ended their relationship after she was spotted kissing a mystery man on the beach in Malibu, California, in July 2014.

Six months later, Paris seemed to take a thinly-veiled jab at her ex on Instagram. 

She shared a drawing of a Bettie Page-type woman with the message: ‘I honestly feel bad for my boyfriends after we break up… I wonder how it feels to go back to basics.’

River, 30, continues to model after their breakup, and he has become a star on Instagram where he has more than 546,000 followers.  

AFROJACK – 2011-2012

Paris and the Dutch DJ AfroJack were rumored to be in a relationship at the end of 2011, with insiders telling RadarOnline that they were getting ‘very serious, very fast.’

But after only six months together – in May 2012 – news hit the web that the music producer dumped her. 

‘Paris was smitten with him, but AfroJack just wanted to have fun and not be exclusive with anyone,’ a source told the outlet at the time.

‘He 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.

Rumors started swirling that Paris and AfroJack were in a relationship at the end of 2011. But after only six months together - in May 2012 - news hit the web that the DJ dumped her

Rumors started swirling that Paris and AfroJack were in a relationship at the end of 2011. But after only six months together – in May 2012 – news hit the web that the DJ dumped her

Speaking out! He rep later denies these claims, telling Us Weekly, '[The stories are] 100 per cent not accurate and are coming from inaccurate sources'

Speaking out! He rep later denies these claims, telling Us Weekly, ‘[The stories are] 100 per cent not accurate and are coming from inaccurate sources’

‘Paris would love to be married with kids, it’s all she ever talks about, but she hasn’t found her Prince Charming yet and she isn’t getting any younger.’  

Her rep later denied these claims, telling Us Weekly, ‘[The stories are] 100 per cent not accurate and are coming from inaccurate sources. Paris and AfroJack are best friends and love and support each other very much. Nothing has changed.’

AfroJack, whose real name is Nick Leonardus van de Wall, was in his early 20s when he dated Paris, who was six years older, but they kept in touch. 

In 2013, it was reported that he was producing her second album, but he later claimed her fame was too much for him to handle.  

‘I’m still in touch with Paris, but musically we’ve taken different paths,’ he told Digital Spy in 2014. ‘There was so much bulls**t surrounding everything because she is who she is. I gave her a shot, but eventually, enough is enough.’ 

AfroJack, 34, later found love with Italian singer Elettra Lamborghini. They wed in Lake Como, Italy, in September 2020 after announcing their engagement the year before. 

CY WAITS – 2010-2011  

Paris and Cy Waits, who owned the nightclubs Wynn and Encore in Las Vegas, Nevada, were together for a year in 2010 and 2011, but their relationship wasn’t exactly easy.

The duo actually got arrested together in Las Vegas after they were pulled over and police found drugs in the car. 

Paris confirmed the split from Cy, now 46, in June 2011, saying they were still close.  

‘We’re not together anymore,’ she said. ‘I love him and we remain really good friends. … I feel like the relationship ran its course and we’ll see what happens.’

Paris and Cy Waits, who owned the nightclubs Wynn and Encore, were together for a year in 2010 and 2011, but their relationship wasn't exactly easy

Paris and Cy Waits, who owned the nightclubs Wynn and Encore, were together for a year in 2010 and 2011, but their relationship wasn’t exactly easy

The duo actually got arrested together in Las Vegas, Nevada, after they were pulled over and police found drugs in the car

The duo actually got arrested together in Las Vegas, Nevada, after they were pulled over and police found drugs in the car

After the breakup, Cy publicly slammed Paris and said their relationship didn't have 'honesty, strong values, true communication, commitment, or mutual trust and respect'

After the breakup, Cy publicly slammed Paris and said their relationship didn’t have ‘honesty, strong values, true communication, commitment, or mutual trust and respect’

A month later, Cy admitted that their split was for the best, saying it was a long time coming. 

‘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,’ he told People in July 2011. 

‘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.

‘When I’m involved with someone, my focus is keeping them safe, trying to keep them out of trouble and always being supportive.

‘Partying is not my thing. I live a healthy lifestyle. I avoid drugs. … I have a social cocktail every now and then.’ 

DOUG REINHARDT – 2009-2010

Paris and baseball player Doug Reinhardt were together for 14 months before they called it quits in April 2010.

After they went their separate ways, she told Us Weekly: ‘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.’

Amid their messy slip, a source told RadarOnline that the sports star spent $2 million over the course of their relationship.

Looking back: Paris and Doug Reinhardt were together for 14 months before they called it quits in April 2010

Looking back: Paris and Doug Reinhardt were together for 14 months before they called it quits in April 2010

After they went their separate ways, she told Us Weekly: 'I just realized that I'm better off without him. So I ended it because I deserve something much better'

After they went their separate ways, she told Us Weekly: ‘I just realized that I’m better off without him. So I ended it because I deserve something much better’

Amid their messy slip, a source told RadarOnline that the former baseball player spent $2 million on Paris over the course of their relationship

Amid their messy slip, a source told RadarOnline that the former baseball player spent $2 million on Paris over the course of their relationship

‘Doug never used Paris. He spent $2 million on her over the course of a year and a half,’ the insider revealed. ‘She never once paid for a single thing. She didn’t so much as pay for a cup of coffee the whole time they were together.

‘Doug even added her to his American Express credit card and she had carte blanche spending permission. Plus he would let her fly all the time on the Reinhardt family jet – even if she was on her own, Doug would charter it for her.’

Doug, who had appeared on the Hills, was also previously linked to Lauren Conrad and Amanda Bynes. He got engaged to his high school sweetheart, Allie Lutz, in January 2013, but they broke up less than a year later.  

He went on to marry Natalie Sutton, who allegedly assaulted him with a crutch in 2018. They divorced later that year.    

Doug, 36, became a dad in 2019 when he and his fiancée Mia Irons welcomed twin boys Maverick and Beau. 

BENJI MADDEN – 2008 

Paris and Good Charlotte singer Benji Madden seemed like total couple goals when they dated in 2008. They were introduced by Paris’ longtime friend, Nicole Richie, who is married to Benji’s brother, Joel Madden.

‘We’ve actually been friends for over six years now,’ Paris said during an appearance on David Letterman in 2008. ‘When [Nicole] had [her daughter] Harlow, I started going over to the house and we got a little crush on each other and totally fell in love.

Paris and Good Charlotte singer Benji Madden seemed like total couple goals when they dated in 2008. They were introduced by Nicole Richie, who is married to Benji's brother, Joel Madden

Paris and Good Charlotte singer Benji Madden seemed like total couple goals when they dated in 2008. They were introduced by Nicole Richie, who is married to Benji’s brother, Joel Madden

Never forget: They were together for nine months before they broke up in November 2008

Never forget: They were together for nine months before they broke up in November 2008

‘We’re like sisters and they’re twins, so it works out well. Nicole and I would be sisters-in-law. We talk about it.’

They were together for nine months before they broke up in November 2008. 

‘She is saddened by the breakup but they’re just too different and they wanted different things in life,’ a source told People Magazine at the time. ‘He was loyal and sweet but it was time to take a break.’

Benji, 42, went on to marry actress Cameron in January 2015. Nearly five years later, they welcomed their first child, daughter Raddix, in December 2019. 

STAVROS NIARCHOS – 2005-2006

Paris and Stavros Niarchos III, who is the son of a Greek billionaire shipping tycoon, started dating in 2005 and were together for about a year before they split.

The hotel heiress was seen partying with Stavros just hours after she confirmed her breakup with Paris Latis, who also happened to be a Greek shipping heir. 

The relationship prompted a feud between Paris and Mary-Kate Olsen, who dated Stavros for five months before he moved on with the socialite. 

In a December 2005 interview with W magazine, Mary-Kate said she had unwittingly introduced Paris to Stavros.   

Paris and Stavros Niarchos started dating in 2005, and were together for about a year before they split

Paris and Stavros Niarchos started dating in 2005, and were together for about a year before they split

It's over! 'I confirm that she’s split with him. They are no longer a couple. I don’t know the exact day they split,' her rep told People Magazine in May 2006

It’s over! ‘I confirm that she’s split with him. They are no longer a couple. I don’t know the exact day they split,’ her rep told People Magazine in May 2006

Still friends: Paris and Stavros, who is the son of a Greek billionaire shipping tycoon, must not have ended on bad terms because they were spotted hanging out in November 2008

Still friends: Paris and Stavros, who is the son of a Greek billionaire shipping tycoon, must not have ended on bad terms because they were spotted hanging out in November 2008

“[Paris and I] always only had nice things to say about each other,’ she said. ‘Now I guess you can tell we’re not talking.’

Paris’ relationship with the playboy didn’t last, and their breakup was later confirmed by her rep.  

‘I confirm that she’s split with him. They are no longer a couple. I don’t know the exact day they split,’ her rep told People Magazine in May 2006. 

However, Paris and Stavros must not have ended on bad terms because they were spotted hanging out in November 2008.

Stavros, 36, met his match when fell for Russian art collector Dasha Zhukova, who was previously married Chelsea football club owner Roman Abramovich. 

Dasha, who has two children with her ex, welcomed her first child with Stavros – a baby boy named Philip Stavros Niarchos – in March 2021.  

PARIS LATSIS – 2004-2005 

Paris started dating Paris Kassidokostas-Latsis, a Greek socialite and shipping heir, in December 2004, and they got engaged just eight months later. 

‘I’m so in love and grateful to have found such an honest and loyal person,’ she told Us Weekly at the time. ‘I feel like we were meant to be, and I’m happy to have found someone to spend the rest of my life with.’ 

Paris started dating Paris Kassidokostas-Latsis, a Greek socialite and shipping heir, in December 2004, and they got engaged eight months later

Paris started dating Paris Kassidokostas-Latsis, a Greek socialite and shipping heir, in December 2004, and they got engaged eight months later 

At the time, Paris made headlines after she famously complained that her 24 carat diamond ring (pictured) - which was reportedly worth $4.7 million – was too heavy on her finger

At the time, Paris made headlines after she famously complained that her 24 carat diamond ring (pictured) - which was reportedly worth $4.7 million – was too heavy on her finger

At the time, Paris made headlines after she famously complained that her 24 carat diamond ring (pictured) – which was reportedly worth $4.7 million – was too heavy on her finger

Headed to splits-ville: They called off their engagement fives months later - in September 2005

Headed to splits-ville: They called off their engagement fives months later – in September 2005

At the time, Paris made headlines after she famously complained that her 24 carat diamond ring – which was reportedly worth $4.7 million – was too heavy on her finger. They called off their engagement fives months later – in September 2005.

‘I’m sad to announce that I’ve called off my engagement,’ she said in a statement. ‘Over the last couple months I’ve realized that this is the right decision for me.

‘We remain best of friends, and I’ll always love him. I hope people will respect my privacy during this emotional time.’

NICK CARTER – 2004

Paris and Backstreet Boys alum Nick Carter had a brief fling in 2004, but according to the singer, it was not a healthy relationship. He told People Magazine that they met through his bodyguard, but that their romance was ‘totally based on distrust.’

When asked if they had cheated on each other, Nick added, ‘The only comment I’m going to have to that is that I’m loyal to those who are loyal to me.’ 

Paris and Nick Carter had a brief fling in 2004, but according to the Backstreet Boys singer, it was not a healthy relationship. He told People Magazine that it was 'totally based on distrust'

Paris and Nick Carter had a brief fling in 2004, but according to the Backstreet Boys singer, it was not a healthy relationship. He told People Magazine that it was ‘totally based on distrust’

He later wrote in his autobiography: 'Paris was the worst person in the world for me to hook up with. [She] fed my worst impulses as far as partying’

He later wrote in his autobiography: ‘Paris was the worst person in the world for me to hook up with. [She] fed my worst impulses as far as partying’

The reality star respond to his claims, and said she 'doesn't believe she was a negative influence on him'

The reality star respond to his claims, and said she ‘doesn’t believe she was a negative influence on him’

He later wrote in his autobiography: ‘Paris was the worst person in the world for me to hook up with. [She] fed my worst impulses as far as partying.’  

The reality star respond to his claims, and said she ‘doesn’t believe she was a negative influence on him.’

‘I’m glad he got help for his problems and wish him all the best,’ she added.

DERYCK WHIBLEY – 2003

The internet was pretty shook when Paris and Sum 41 rocker Deryck Whibley were spotted kissing and cozying up in 2003. 

There’s not much information on Paris’ relationship with the singer and songwriter, who went on to marry rocker Avril Lavigne, whom he was wed to for three years. 

Neither Paris or Deryck ever commented on why their romance came to an end, sparking speculation that the relationship simply fizzled out.  

The internet was pretty shook when Paris and Deryck Whibley were spotted kissing and cozying up in 2003

The internet was pretty shook when Paris and Deryck Whibley were spotted kissing and cozying up in 2003

There's not much info on Paris' relationship with the musician, who was later married to Avril Lavigne for three years, however, things must have eventually fizzled out between them

There’s not much info on Paris’ relationship with the musician, who was later married to Avril Lavigne for three years, however, things must have eventually fizzled out between them

JASON SHAW – 2002-2003

Paris’ first fiancé was model Jason Shaw. They started dating in 2002 and got engaged shortly after, although very little information was ever shared about the proposal – or the ring, despite Paris being seen sporting a very large diamond on her wedding finger on several occasions. 

At the time, she gushed, ‘I love him so much. We’re very close and I’ve known him a very long time.’

She was only 21 years old at the time, while the model was 29, and their eight-year age difference caused some backlash from the media. 

It’s unclear what went wrong in the end, but they ultimately ended their relationship in 2003. They appeared to remain friends and were caught hanging out again in 2010.

Put a ring on it! Paris' first fiancé was Jason Shaw. They started dating in 2002 and got engaged shortly after - however the former couple shared very little information about the proposal, or the ring (which Paris is pictured wearing)

Put a ring on it! Paris’ first fiancé was Jason Shaw. They started dating in 2002 and got engaged shortly after – however the former couple shared very little information about the proposal, or the ring (which Paris is pictured wearing)

At the time, she gushed, ‘I love him so much. We’re very close and I’ve known him a very long time'

At the time, she gushed, ‘I love him so much. We’re very close and I’ve known him a very long time’

RICK SALOMON – 2001

Paris and poker player Rick Salomon’s relationship is probably one of her most famous relationships. Years after they had split – in 2004 – Rick leaked a sex tape of the two, something that left Paris feeling ‘so betrayed.’

‘That will always be something that will hurt me for the rest of my life,’ the socialite said during a Vanity Fair Cocktail Hour, Live! in April 2021. 

‘It’s always there in the back of my mind. When it happened, people were so mean about it to me. The way that I was spoken about on nightly talk shows and the media, to see things with my family was just heartbreaking.

‘I would be in tears every single day, I didn’t want to leave my house, I felt like my life was over. It was a private experience between two people.

‘You love someone, you trust someone and to have your trust betrayed like that and for the whole world to be watching and laughing.

Paris dated Rick Solomon in 2001. Years after they split - in 2004 - the poker player leaked a sex tape of the two, and Paris said the whole thing left her with PTSD

Paris dated Rick Solomon in 2001. Years after they split – in 2004 – the poker player leaked a sex tape of the two, and Paris said the whole thing left her with PTSD

Paris said after he released the sex tape (pictured), she felt like 'her life was over.' She added: 'I would be in tears every single day, I didn’t want to leave my house'

Paris said after he released the sex tape (pictured), she felt like ‘her life was over.’ She added: ‘I would be in tears every single day, I didn’t want to leave my house’

It was even more hurtful to me to have these people think that I did this on purpose – that killed me. It still gives me post-traumatic stress disorder to talk about it.’

She also recently opened up about it in her documentary, This Is Paris. She said: ‘It was my first real relationship. 18. I was so in love with him and I wanted to make him happy.

‘And I just remember him pulling out the camera. And he was kind of pressuring me into it. It was like being electronically raped.’

EDWARD FURLONG – 2000

Paris confirmed her romance with actor Edward Furlong while shutting down rumors that she was gearing up to get married.

‘No, we’re not married, but he is my boyfriend. We’ve been going steady together for about a month,’ she told The New York Post in September 2000. 

Although they kept their relationship pretty secret at the time, she later revealed that they were together for eight months in total. He is most known for starring in Terminator 2: Judgment Day, American History X, Pet Cemetery II, and more.

Young love! Paris confirmed her romance with Edward Furlong in September 2000

Young love! Paris confirmed her romance with Edward Furlong in September 2000

Although they kept their relationship pretty secret at the time, she later revealed that they were together for eight months in total

Although they kept their relationship pretty secret at the time, she later revealed that they were together for eight months in total

Read more at DailyMail.co.uk