Enrique Iglesias and Anna Kournikova have been together for nearly two decades and all along the way, they’ve played by their own rules. Their love story includes at least two breakups, a decision to totally avoid marriage, and not one but two top-secret pregnancies.

In 2007, Iglesias told PEOPLE en Español that dating Kournikova was “the only serious relationship I’ve had in my life” and it seems he’s happy to keep it that way. These days, the Grammy-winning singer and legendary tennis player are all about family and raising their three young kids and it looks like they really couldn’t be happier.

Here’s what we can learn from Enrique Iglesias and Anna Kournikova’s unconventional relationship:  

Enrique Iglesias and Anna Kournikova first met on the set of his 2001 music video for “Escape” and, according to People, began dating soon afterwards. All you have to do is watch the clip to see the pair’s undeniable attraction. As Iglesias gushed in a behind-the-scenes video for “Escape,” Kournikova is “beautiful, talented, a great tennis player [and] it doesn’t take a good actor to kiss Anna and try to make it believable!” 

Just a few months later, the pair made their red carpet debut at 2002’s MTV Video Music Awards and, in 2004, they sparked engagement rumors when Kournikova showed up at a World Team Tennis match wearing a huge diamond ring. Soon, rumors of a secret wedding in Puerto Vallarta, Mexico began to swirl, but sources were quick to tell People that the couple was not married.

Marriage just isn’t for everyone 

Enrique Iglesias and Anna Kournikova (Photo by Ralph Notaro/Getty Images)

If one thing has become clear over the years it’s that Enrique Iglesias and Anna Kournikova don’t really see the importance of marriage — and that’s okay. Luckily, they’re on the same page when it comes to tying the knot, which has meant a happy relationship on their terms. 

As Kournikova confidently told People in 2008, “I’m never getting married.” Meanwhile, Iglesias told Parade in 2012 that although he’s occasionally called Kournikova his “wife” in public, they’re not technically married because “I’ve never really thought marriage would make a difference.” Explaining his approach to matrimony, he continued, “Maybe it’s because I come from divorced parents, but I don’t think you love someone more because of a piece of paper. And nowadays, it’s not taboo to have kids and not be married,” he reasoned. “What makes a difference is that you’re a good parent, period.”

The “Bailando” singer shared the same sentiment in 2014, telling CBS Sunday Morning, “I’m not against marriage, not at all, but when you’ve been with someone for such a long time, I don’t think it’s going to bring us any closer together. I do not think it’s going to make us any happier,” he said. 

Just because walking down the aisle is a tradition some couples choose to take part in, it doesn’t make a relationship without marriage any less valid. Just ask Anna Kournikova. “I’m in a happy relationship with Enrique, that’s all that matters,” she explained in 2019.

Marriage isn’t important to me. I believe in being open and trusting each other and respecting each other completely. We’ve been together for years,” she continued, adding that their union works because “he’s the male version of me, and I’m the female version of him.

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Taking time apart doesn’t have to spell failure 

It’s unclear how many times the couple has actually split throughout their 19-year dating history, but what we do know is that it hasn’t always been smooth sailing.

Explaining the inspiration for ‘Enamorado Por Primera Vez’ during a 2019 concert, Iglesias got candid about his love life, telling the crowd (via Hola), “I’ve been with my girlfriend for 17 years. We’ve had good times and bad times. Moments when I wanted to end it. (When I thought) ‘I can’t take it anymore.” 

Iglesias wasn’t the only one to experience those feelings. As he revealed, “There was one time — well, two times actually — that [Anna] told me ‘that’s enough, I’m done.’ And I remember — and this is the truth — that I wrote this song to say sorry,” he said of ‘Enamorado Por Primera Vez,’ noting he used the track to win her back. 

While it’s unclear when those two times might have been, Iglesias did tell Swedish newspaper Aftonbladet in 2007 that he and Kournikova were “divorced. I am single now, but that’s okay. I don’t mind being alone,” he said. However, his rep quickly denied the split, telling People that Iglesias was joking and “they are still together.”

Jump to 2014 and the singer made a similar announcement, telling reporters he “got a divorce three days ago and I wanted to give you guys the exclusive. I’m serious. No, seriously. Don’t laugh.”

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They’re all about their family these days

Despite facing bumps in the road, Enrique Iglesias and Anna Kournikova realized they had something special that was worth fighting for. As Iglesias told CBS Sunday Morning, from the moment he met his girlfriend, he knew she was special. “She was just the coolest girl in the world to me and we just — we got along,” he noted. 

Once the pair realized they did indeed want to be together, they switched their focus to family. In December 2017, they welcomed twins Nicholas and Lucy after a top-secret pregnancy, then, in January 2020, they had daughter Mary.  

The additions brightened up their lives and brought them closer together. As Kournikova told The Sunin 2019, “I love being a mom. I absolutely wanted to have children, whether I had my own or adopted,” she explained, adding, “I love taking care of people.”

Meanwhile, Iglesias opened up about fatherhood during a concert soon after the arrival of their twins, saying, “I became a father 12 weeks ago and I can absolutely tell you two things, without the slightest doubt, I love my babies. Actually, three things, I love my girl, and I love you guys for being here tonight,” he joked. And when Entertainment Tonight asked him what it was like to be a dad of three in March 2020, he gushed, “I’m not sleeping, but I’m having a great time! I mean, I wouldn’t change it for nothing in the world.”

Relationships aren’t always perfect, especially when they last as long as Enrique Iglesias and Anna Kournikova’s union has. It’s normal to not always agree and, sometimes, it takes walking away to help you realize you’re actually meant to be together.

Despite the struggles they experienced around the five-year mark, Iglesias and Kournikova felt they had something special and so, they found a way to work through the difficulties and build a relationship that now suits them perfectly. Rather than following the norm, they decided to do things their way and, seeing as they’ve been dating for 19 years and counting, it’s obviously working!

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