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Flings, fiances and guys she's pashed: Sophie Monk's fascinating dating rap sheet

We look at Sophie Monk's very enviable love life.

By Chloe Lal
Sophie Monk is so much more than a triple threat.
Sure she's a model, singer and actress but she's also super hilarious, witty and the kind of girl we all wish was our BFF.
Although the 41-year-old is gorgeous, she has confessed that good looks aren't a huge factor when looking for a partner.
"I get brain crushes", she explained, "it takes me a long time and then I fall in love with their brain... so bad, I wish I fell in love with looks but I don't."
As Sophie Monk prepares to walk down the aisle, We decided to look back at the big loves, heartbreaks and a few mistakes that have led her to this moment.

Jason Statham: 2005 - 2006

Jason is one of Hollywood's biggest action heroes.
Sophie and Jason Statham hit it off in 2004 after meeting on the set of indie drama London.
The British actor had just broken up with partner of seven years Kelly Brook, when talks of a romance with the Bardot songstress started swirling.
The pair dated for 11 months before ending things in August 2006.
In 2017, Sophie confirmed the speculation surrounding their dalliance, sharing they had indeed "banged" on Kyle and Jackie O's radio segment Banged Or Haven't Banged.
These days Jason, 53, is happily engaged to 34-year-old model Rosie Huntington-Whiteley and they're the proud parents to their baby boy Jack Oscar.

Benji Madden: 2006 - 2008

One of her most iconic romances.
The singer was once engaged to Good Charlotte member Benji Madden.
The duo began dating in 2006 and the following year Benji popped the question on Christmas Eve 2007.
Things took a turn for the worst, and in February 2008 the couple split.
"Sophie and Benji have officially split. The decision was mutual and they remain amicable," her agent announced in a statement.
Despite the statement, the 41-year-old has shared many awkward tales since they ended things.
In 2014, she recalled a very uncomfortable run-in at a restaurant, confessing to 2DayFm: "When you see an ex your body doesn't know what to do."
"I like to break the ice," Sophie recounted, "so I walked over and said 'Hi, how are you?" and my body just threw over him and my arms hugged him."
He proposed in 2007.
Sadly, Soph got nada from the Madden twin.
"No arms back, no hug, he just stood there like 'What are you doing?'" More recently, Sophie shared that her ex-rocker beau still has some of her things.
"He's got some of my belongings [that] I need back still... I think my mum's engagement ring."
The beloved Aussie has no hard feelings for her muso ex, who is now married to Cameron Diaz.
"I want him to be happy, so if he's found someone that makes him happy that's awesome," she told the Telegraph.

Ryan Seacrest: 2008

Their dates sound magical!
In April 2008, following her split with Benji Madden, the Aussie was spotted with American media heavyweight Ryan Seacrest.
Speaking out about their brief time together, Sophie revealed that the now 46-year-old once took her to Ellen DeGeneres' birthday party.
"I went on a date with him-ish (sic), kind of thing, I don't know," she admitted during a chat with Sonia Kruger and David Campbell.
"He took me to Ellen DeGeneres' party, birthday party. He arrived by helicopter and I came in my car. And I was like, 'ballin'," she laughed.
"I had to meet him there, he was a bit busy."
Adding, "He's really, really nice."
Watch Sophie chat about dating Ryan in the video player below!

Joe Francis: 2008

Joe is most famous for creating the Girls Gone Wild brand.
Joe Francis is the founder of Girls Gone Wild.
The 48-year-old American entrepreneur was linked to Sophie in August 2008.
While the pair were spotted on numerous occasions, Sophie has denied any romantic relations with Joe.

John Diaz: 2010

The pair in happier times.
Sophie first started dating plastic surgeon John Diaz in 2009 but called it a day the following year after finding him in bed with another lady.
Speaking about her cheating ex, Sophie told Kyle and Jackie O she was "Sandra Bullock-ed."
"I rock up in the morning with a coffee and presents and he [Diaz] had a present there—a chick."
The singer explained she quickly jumped in her car and sped off, but decided to return to his place and confront him.
"I walked back in and went, 'What's going on?' and actually had a conversation. I spoke to the girl. She was in shock. I didn't know her. She was innocent."
Being our real-life hero, Sophie left the apartment and "very strategically" spilt coffee all over his car.

Kevin Connolly: 2010

Sophie met Kevin on the set of Entourage.
Sophie first met actor Kevin Connolly in 2007, on the set of Entourage.
The duo went on to have a brief fling during the same time she was breaking up with John Diaz.
Her past became a topic of conversation during a 2014 interview with Entourage creator and actor Mark Wahlberg.
"I've got gossip.. because Kevin Connolly is your good friend isn't he," the singer began to ask before her co-host, Jules Lund decided to interrupt, "These guys were shagging for a while."
Trying to divert attention, Sophie said, "I went on dates with him, we didn't go past second base," before storming off. She has since admitted that they had "banged."
Check out the VERY awkward encounter below!

Russell Simmons: 2010

Russell was spotted being very touchy with the blonde bombshell.
Sophie was linked to Russell Simmons in 2009/2010.
The Aussie was working with the rap mogul on her now-canned reality show Bigger than Paris.
The pair were spotted leaving a Maxim Hot 100 party in LA together, with Russell tweeting, "Leaving Maxim 100 party took my client Sophie monk lots of fun .. Producing her show will be real pleasure."

Jimmy Esebag: 2011

Their romance was short-lived.
Sophie shocked the country when she announced she was engaged to French businessman Jimmy Esebag, back in January 2011.
Speaking to her friends Kyle and Jackie O about her man, she gushed, "I got engaged, and I kept it quiet so no one's heard much about him. He's a keeper. It feels right — I think you know when you know."
Sophie had described Jimmy, who is 20 years her senior, as "a male version of myself."
Months later the pair called it off.
Being a real trooper, Sophie told Chelsea Handler she may even date a girl, confessing she'd "join Team Samantha Ronson."

Ray J: 2012

Fans will recognise Ray J from his days with Kim Kardashian.
Many would know singer Brandy's brother, Ray J as the guy from Kim Kardashian's sex tape.
At this point, we're going out on a limb and say Sophie has had some pretty solid celeb dates.
But Ray J would take the cake... If it happened.
The were linked together back in 2012, when they shot a very steamy ad campaign together... And then she was allegedly spotted leaving his place at 8:30am the next morning.
Sophie has always been pretty up front when it comes to the men in her life.
She told GlobalGrind, "I have some skeletons in my closet, but Ray J is not one of them."

Sam Worthington: 2013

Sophie with Sam, back in 2013.
Before Lara Bingle, Sam Worthington was dating the nation's Popstar.
They were first linked in April 2013 but they tried to downplay their sizzling romance.
Sophie was forced to announce they were a couple during a radio prank, but things weren't meant to be with Sam telling a rival radio show he was smitten with new girlfriend Lara Bingle.
At the time, Soph said "it really hurts" seeing images of the couple.
"I wanna be happy for them, but it really annoys me," she bravely admitted.
Relive the incredible moment Sophie confirmed she was dating Sam, only for the Hollywood star to share details of his new romance with Lara Bingle.

Sophie on Tinder: 2014

Ready to mingle!
Like any single gal, Sophie joined Tinder in 2014.
At the time, there was talks she was dating Buddy Franklin.
Speaking on her radio show, she told listeners her colleagues set the account up for her.
"They've noticed that I moved here, I've got no friends, and no one to hook up with really... they set up a [Tinder] account for me!" she shared.
Before adding, "It's time to Tinder."

Eric Grothe Jr: 2016

LSophie revealed she was dating ex-NRL player Eric Grothe Jr in 2016.
The couple were on and off for a few years, but things came to a crashing holt.
Confiding to Kyle and Jackie O, she shared, "We've been dating on and off for, like, a couple of years, and no-one really knew. You know how it is when you [go] public, and it creates drama. We wanted to keep it special. It's been on and off forever, but now it's off again."

Stu Laundy: 2017-2018

Her got her rose but not her heart. Instagram
In the final episode of Sophie's turn as The Bachelorette in 2017, she gave her final rose to Stu Laundy.
It seemed like the star had finally found her happy ending when she said, "I've never been as happy as that moment," in the final episode, but soon after, things took a turn for the worse.
Sophie confirmed their split in January 2018, and she credited her desire to have children as the reason they parted ways.
"I went into this experience looking to settle down and start a family. I gave it the best shot I could, and my intentions were everything I said I was looking for, but unfortunately, it just didn't work out," wrote Sophie.

Shane Warne- 2018

It was just a tiny moment between Shane and Sophie. Instagram
Sophie accidentally revealed in 2018 on Fitzy and Wippa's radio show that she had hooked up with the Australian cricketer.
Fitzy initially asked the Love Island host if Shane had asked her out on a date before.
Sophie replied, "Yeah, I love Warnie, he's cool... We've hung out a few times, with pants on, if that's what you're asking."
When she was asked if they had shared a kiss, she admitted there was a cheeky little moment between them.
"Uhhhh..... ummmm," she stuttered. "But just a cheeky, nothing serious!"

Joshua Gross- 2018-present

Joshua is Sophie's one and only. Instagram
Sophie may not have achieved love on The Bachelorette, but she found her happily ever after with Joshua Gross, 42, who she met on a plane in 2018.
When Sophie was asked about their rom-com meeting, she revealed to 9Honey that his sense of humour enthralled her.
"I just sat down, and he had a sense of humour, and I was like, 'Oh, how relieving, sitting next to someone you can have a chat with'," Sophie told the publication.
"It was like, 'Good sense of humour, hard worker'… it just happened."
Joshua is Sophie's endgame after he proposed to the star in January 2021.
The Beauty and the Geek host announced the news on her Instagram.
She wrote, "Told you I'd tell you guys first💍🙌 I'm engaged.
"I honestly can't thank you enough for all the love and support. I know I have the coolest people following me, and you've always had my back, and I feel so cared about. You're absolute bloody legends. I'm not very good at being mushy. I'm trying to say I absolutely adore you."