Simon Cowell & Lauren Silverman’s Relationship Timeline: From Affair To Baby & Engaged

Simon Cowell is engaged to his partner Lauren Silverman, 44 after 13 years of dating! The pair, who are parents to son Eric, 7, have definitely had quite the ride along their romance journey, from a love-at-first-sight meeting to a rocky dating beginning to welcoming a child. Here we break down the TV personality and his socialite love’s relationship timeline, from early beginnings to saying “I do.”

How Simon & Lauren Met

Simon and Lauren first met at Barbados’ Sandy Lane resort in 2004 when the socialite was vacationing with then-husband, real estate mogul Andrew Silverman. It was love at first sight for the soon-to-be-involved pair, as sources reported Simon’s setting his sights on Lauren from the get-go. All the same, Simon continued to date other women, including Terri Seymour, an entertainment journalist, and makeup artist Mezhgan Hussainy. Simon was even engaged to Mezhgan from 2010 to 2011 but later reported it to be a “big mistake.”

A Scandalous Affair

Simon and Lauren didn’t exactly have an easy start to their relationship. After they met, they began seeing each other even though Lauren was still married to Andrew. They kept their relationship secret, although Lauren became pregnant in 2013, thrusting the couple in the position of admitting to their affair.

Following the public acknowledgement of the relationship, Andrew filed for an at-fault divorce citing adultery and he and Lauren finalized their divorce in November of that year. In their settlement, there was a strict stipulation that Simon was to stay away from Lauren and Andrew’s son, Adam, or face a penalty of $50,000.

“[The affair] is not something I am proud of or wanted to happen in terms of hurting anyone,” Simon previously said of his early relationship with Lauren. “It just happened … But then, of course, you have a baby, and you look at the baby and you kinda go, ‘This is what happened from it.’”

Welcome Baby Cowell

Lauren gave birth to their son Eric (named after Lauren’s father) on February 14, 2014. Although Simon noted to the Daily Mail in 2018 that fatherhood definitely changed him for the better, he also shared that the change wasn’t exactly an easy feat. “During the first eight or nine months I was thinking, ‘I don’t think he likes me very much.’ He does remind me of me when I was younger because he knows how to try it on and how to get away with things,” Simon told Entertainment Tonight in 2016.

Becoming a father late in life was also a major shift for the TV show host, but he now says he can’t imagine his life without Eric. “[Time flies] like you wouldn’t believe,” Simon said back in 2019 of fatherhood. “I said to someone the other day, ‘It’s much easier than I thought.’ And then you can’t imagine ever not having him … It’s the most amazing feeling,” he gushed.

Simon and Lauren have all the love in the world for their one son, but they’ve definitely discussed adding more members to their family. “”I had a brother when I was younger so I think it’s kind of cool to have two,” Simon told Extra after his son’s birth in 2014. “Well, two or three.”

Engagement & Future Plans

After spending 13 years together as committed partners, the duo made an official commitment to be wed while on vacation in Barbados. The 62-year-old TV personality reportedly popped the question at the island locale, a source told Page Six, with both Simon and Lauren’s kids present. “It was super sweet,” a source told Page Six about the proposal, adding that “they’re good together.” Simon also owns a home in Barbados, where the family is seen vacationing on an annual basis.