Simon Cowell and Lauren Silverman’s Relationship Timeline

Simon Cowell is an engaged man!

The America’s Got Talent judge proposed to his longtime love Lauren Silverman in December 2021, and the couple are currently planning their wedding.

Cowell and his fiancée first met in 2004 while on vacation in Barbados, although Silverman was married to businessman Andrew Silverman at the time. Years later, Cowell and Silverman began quietly seeing each other and in July 2013, PEOPLE confirmed that the couple were expecting a child together and that the Silvermans had filed for divorce.

Meeting Silverman was clearly a game-changer for the British television personality — prior to their relationship, Cowell had made public statements about not knowing if he ever wanted to get married or have kids.

Since welcoming their son Eric in 2014, however, Cowell has said he loves being a father.

“From that moment I saw the scan, I was like ‘That is it, I’m besotted.’ Now I just cannot imagine my life without him,” Cowell said of his son during an interview with Kelly Clarkson. “He’s the most amazing thing that ever happened to me. I adore him.”

From welcoming a son together to their beach engagement in Barbados, here is everything to know about Simon Cowell and Lauren Silverman’s relationship.

Early 2004: Simon Cowell and Lauren Silverman meet in Barbados

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Cowell and Silverman first met in 2004 in Barbados. Silverman, an entrepreneur and socialite, was on vacation with her then-husband, whom she shares one son with.

The TV personality and Silverman maintained a friendship for many years while Cowell continued to date other women. From 2002 to 2008, he was in a relationship with entertainment journalist Terri Seymour, and he was later engaged to makeup artist Mezghan Hussainy from 2010 to 2011.

May 2012: Rumors circulate that Simon Cowell and Lauren Silverman are having an affair

In May 2012, rumors began to surface that Cowell and Silverman were in a relationship. Cowell’s lawyer initially denied the rumors and said in a statement, “Any implication or statement that my client is engaged in adultery and has allegedly broken up the marriage of Ms. Silverman is not only false but reckless.”

July 2013: Simon Cowell and Lauren Silverman are expecting a baby together

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In 2013, multiple sources confirmed to PEOPLE that Silverman was pregnant with Cowell’s child. PEOPLE also reported that the Silvermans had filed for divorce. When asked for comment, Cowell’s U.K. rep said, “This is a very sensitive issue and all media enquiries are being dealt with by his U.S. attorney.”

A source also told PEOPLE that Silverman had been “unhappy in her marriage” for a while and that she was “ecstatic to be with Simon.” The source added that the pair had been seeing each other for more than a few months.

After the pregnancy news broke, Silverman’s estranged husband released a statement. “My top priority is protecting my 7-year-old son while working to resolve all outstanding issues with my wife,” he said, adding, “hopefully people can respect the interest of our child during this process.”

In a separate statement, Silverman said, “I am committed to sorting things out with Andrew as amicably as possible to ensure the well-being of our son. I would hope for some space and privacy in order to work through this.”

August 21, 2013: Simon Cowell and Lauren Silverman vacation in France

Soon after her divorce was finalized, Cowell reunited with Silverman for a vacation in the South of France. “He is very pleased that her divorce is finalized, and he is excited about spending time with Lauren,” a source close to Cowell told PEOPLE. “He wants to make sure that she and the baby are doing okay. He is getting more and more excited about the baby.”

The couple strolled hand-in-hand on the beach as Silverman showed off her baby bump.

February 14, 2014: Simon Cowell and Lauren Silverman welcome a son

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The couple welcomed a son, Eric Philip Cowell, on Feb. 14, 2014. He was named after Cowell’s late father.

March 5, 2014: Simon Cowell and Lauren Silverman want to have more kids

In March 2014, Cowell opened up to Extra about fatherhood and shared that he and Silverman had already begun discussing having more children. “I had a brother when I was younger so I think it’s kind of cool to have two. Well, two or three,” he said.

Cowell also shared that he was initially nervous about becoming a father, but said that quickly changed once Eric was born.

“I actually said to Lauren beforehand, ‘What if I like the dogs more than him?’ and she said, ‘You’re gonna be absolutely fine,’ ” the former American Idol judge recalled. “And then literally within seconds of him being born, I got it! I was born to be a dad.”

June 2, 2014: Simon Cowell and Lauren Silverman make their first public appearance since welcoming their son

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Four months after welcoming Eric, Cowell and Silverman attended the Health Lottery Tea Party at The Savoy in London. The couple coordinated in shades of white and smiled for photos. The event marked their first public appearance together as parents.

February 24, 2015: Simon Cowell and Lauren Silverman attend the ELLE Style Awards

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Cowell was honored with the outstanding contribution to entertainment award at the ELLE Style Awards in February 2015. Silverman was right by his side to show her support and the pair smiled for photos on the red carpet.

December 2015: Simon Cowell and Lauren Silverman vacation in Barbados

The Cowell-Silverman family spent the 2015 holidays together in Barbados. The pair were spotted jet skiing before Cowell posed with fans for pictures.

February 24, 2016: Simon Cowell and Lauren Silverman make their Instagram debut

On Feb. 24, 2016, Cowell posted an Instagram photo of himself and Silverman holding hands at the 2016 BRIT Awards. The post marked one of the rare occasions Silverman has made an appearance on Cowell’s account, as the couple typically keep their relationship very private.

June 2, 2016: Simon Cowell opens up about family life with Lauren Silverman

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Two years after the birth of their son, Cowell gave PEOPLE an update on his family and shared how fatherhood has changed his demeanor on America’s Got Talent.

“Lauren is great,” Cowell said, before admitting that having a kid has “softened” him up a bit as a judge on the NBC competition show. “There’s no question when you actually have a kid, it does make you feel different because you understand how you would feel if it was your son up there,” he shared.

He added of his son, “He’s exactly like me when I was younger, he’s so cheeky, and he knows how to get me wrapped around his little finger.”

August 22, 2018: Simon Cowell thanks Lauren Silverman at Hollywood Walk of Fame ceremony

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In August 2018, Cowell was honored with a star on the Hollywood Walk of Fame. He was joined by Silverman, their son Eric and Silverman’s older son Adam. The family posed for pictures together, and Cowell also gave Silverman a special shout-out during his speech.

“Lauren, you’ve been my rock for the past few years, put up with everything I put up with,” he said. “I suppose one thing I was also thinking about today was who would have got a bigger kick out of this? My mom and dad. And they’re not here, but I have a feeling they’re looking down, and now I can look over to my son Eric and say, ‘Maybe one day you’ll get one of these as well.’ ”

October 29, 2018: Simon Cowell and Lauren Silverman attend the Pride of Britain Awards

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Cowell and Silverman enjoyed a date night out at the 2018 Pride of Britain Awards in London. The couple got glammed up for the occasion and smiled as they walked the red carpet and posed for pictures together.

August 8, 2020: Lauren Silverman helps Simon Cowell recover after bike accident

In August 2020, Cowell was hospitalized after falling off his electric bike near his and Silverman’s home in Malibu, California. He broke his back in three places and had to undergo a five-hour surgery to repair his spine.

Cowell spoke about the experience and the recovery process in an exclusive interview with PEOPLE. “I was so embarrassed about coming home looking about 100 [years old] because I couldn’t walk, and I have these metal rods in my back and these screws,” he said.

“I said, ‘Lauren, I just don’t know how to explain it to [Eric],’ ” he continued. “She obviously said something to him because he came in … and I was lying in bed and he said, ‘Daddy, you’re like Iron Man,’ and I thought that was the sweetest thing and it meant a lot.”

May 26, 2021: Simon Cowell says having a kid with Lauren Silverman brought out his softer side

During an appearance on The Kelly Clarkson Show, Cowell discussed parenthood as well as the seven-book children’s series he had begun writing with his son.

“It’s been brilliant,” Cowell said of the book series, which is titled Wishfits. “I never thought I would do something like this.”

Clarkson then commented that he seemed like a “different dude” since becoming a dad, adding that she thought his “vulnerable side” had come out.

“Maybe,” Cowell responded. “After I lost my parents, I genuinely felt, Kelly, I would never feel that kind of love for anyone ever again. I thought that was it … until I saw the scan of [Eric] for the first time.”

December 24, 2021: Simon Cowell proposes to Lauren Silverman

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After nearly a decade of dating, Cowell proposed to Silverman on Christmas Eve while on a family vacation in Barbados — where the couple first met.

A source told PEOPLE that Cowell surprised Silverman while on a beach walk, dropping down to one knee and popping the question. Their son Eric and Silverman’s older son Adam were also present.

“They are both super happy,” the source said of the newly engaged couple. “They’ve been together a long time now and adore each other so it’s not a huge surprise to their close friends.”

Another source told PEOPLE that Cowell and Silverman were meant to be together, calling the pair “soulmates.”

“They have fun together, as well as being each other’s rock,” the insider added. “They are both passionate [about one another], but really do bring out the very best in each other. As a family, they all have such an incredible bond.”

Cowell’s brother, Tony Cowell, shared similar sentiments, telling PEOPLE, “Since having his son, Eric, with Lauren, Simon has completely changed his life and, for the first time, he appears to be happy and content.” He added that their late mother would have been “overjoyed” by the engagement news. “She always wanted him to settle down with a family. I picture her looking down and saying, ‘and about time, Simon!’ ” he said.

April 8, 2022: Simon Cowell discusses wedding planning and his engagement to Lauren Silverman

A few months later, Cowell spoke about his and Silverman’s pending nuptials during an interview with The Sun, revealing that he was taking the lead on the wedding planning. “I am planning it all, otherwise I know what will happen — there will be 600 people and it’ll get out of control, like my 50th birthday party,” Cowell shared. “No one knows when it’s going to be — that’ll be a surprise, even for Lauren.”

He added, “I don’t want to have one of these ghastly wedding planners and all the arguments that happen, and who you do invite and who you don’t invite. The whole thing just seems like too much hassle.”

He also told the outlet that his son, Eric, was one of the reasons why he decided to get down on one knee.

“I’ve kind of felt myself engaged for a long time, if I’m really being honest,” he said. “Lockdown and COVID were probably make or break for many relationships. We were in the same house for over a year and I thought, ‘Well, actually, we get on really, really well.’ ”

He continued, “And for Eric, as he gets older, he will be asked more and more about his parents, and I thought it was the right thing to do for him.”

September 14, 2022: Simon Cowell, Lauren Silverman and son Eric attend America’s Got Talent season 17 finale

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Cowell was joined by his fiancée and their son at the season 17 finale of America’s Got Talent. The family of three walked the red carpet together and posed for photos.

February 5, 2023: Simon Cowell and Lauren Silverman visit the Chelsea FC soccer club

Cowell shared photos on Instagram of him, Silverman and their son Eric visiting the Chelsea FC soccer club.

One picture showed the family of three posting with the team’s lion mascots, while in other snaps, Eric was shown meeting soccer star Mason Mount.

“We had the best time at @chelseafc, @masonmount you are such a nice person. Thank you!” Cowell captioned the post.