The Grammy-winning singer and the tennis champ first met in late 2001, when Kournikova took the role of Iglesias' love interest in the steamy music video for his hit "Escape." And while there were some things to sort out before they could be together forever...
It was game, set, perfect match.
"She's beautiful, talented, great tennis player," Iglesias said appreciatively but nonchalantly about his co-star in a Making the Video feature, adding, "It doesn't take a good actor to kiss Anna and try to make it believable."
And so began their tradition of playing coy.
Together for the better part of two decades, they are now parents of three, daughter Mary joining 3-year-old twins Nicholas and Lucy in Jan. 2020. "They actually love it," Iglesias told People in March of that year of how the twins were adjusting to having a little sister. "There's a two-year difference, so I was a little scared. I was like, 'How are they going to react?' And I have two dogs so my house is chaotic. When we first came home with Masha [Mary in Kournikova's native Russia], I was like, 'Oh, how is everybody going to react?'"
Kournikova, for one, added Iglesias to her name on Instagram when Mary was born, sending speculation into overdrive (considering she already had been sporting a wad of sparkly jewelry on that finger for years) that she had finally married the singer after previously insisting she never planned to walk down the aisle. But if they did tie the knot, they're not shouting it from the rooftops.
Over the years they may have gone from toying with the media about whether or not they're still together to sharing ridiculously adorable photos and videos of their children on Instagram, but they still aren't ones to overdo it when it comes to dishing the details of their romantic life. Perhaps when it kicks off with kissing in a video, you feel you've given the public enough for awhile.
Though she did share a teaser for Iglesias' "Subeme la radio" video in February 2017, Kournikova's Instagram page pre-babies mainly revealed that she was deeply committed to working out and in a serious relationship with her beloved dogs, Max and Jack. Same for Iglesias, whose pre-fatherhood account was devoted to touring, music, fans—and the dogs.
He and Anna respectively wished their canine son Jack a happy birthday on Oct. 9, 2017, two months before their pair of human babies were born on Dec. 16 without the couple having let on that they were expecting (though they were snapping pictures along the way). To this day, they remain as low-key about their partnership as ever—and the dogs still factor prominently in their public photo albums.
But about the things that needed sorting out before they settled down...
When Kournikova and Iglesias first met, she was barely 21 and had been linked to two much-older Russian hockey players, Pavel Bure and Sergei Federov, off and on since she was about 16.
She and Federov were said to have first met in Moscow when she was 15. Kournikova moved to Florida for tennis and, as she improved as a player and her model looks made her an instant endorsement darling and lad-mag pinup, Federov was regularly in the picture.
Though she denied a July 2001 rumor that they secretly got married in Russia (ring watch is timeless, people), Federov claimed to The Hockey News in 2003 that they had been married, "albeit briefly, and we are now divorced" (as well as no longer in touch). She was also rumored to have been engaged to Bure—who knew Federov from the Russian national team—as late as 2000. She and Bure both denied being engaged.
What a web.
"While I don't typically comment on my personal life, let me confirm once again that I am not married," Kournikova stated on her website. According to the Telegraph in 2003, she later responded to a request for comment with, "Why don't you go and find out? I really don't want to talk about it."
Federov said yet again in 2005, talking to ESPN.com, that he and Kournikova were briefly married—and that their relationship was, for one thing, misunderstood, and that it had its highs and lows.
"The best thing was that we were both Russian. There was no romance for a long time. She was just a kid when we met the first time," Federov, who's 11 years older than Kournikova, said. "Our families got along. We had a lot in common, we lived similar lives, we understood each other. So our friendship developed 'cause we were in the same position professionally and socially."
The progression to romance came as a surprise to him, he recalled.
"We spent quite a few days together," the athlete told ESPN. "Anna expressed that kind of interest, I was kind of surprised because I was a little bit older and wilder than her and I was going in a different direction. But I looked at the situation and said she was a great person, so why not? So, then we started dating. It was tough because her schedule had her based all over the world and I played games in so many different cities."
Their marriage, Federov continued, was the "same as the normal life we led before. We were both glued to our schedules. It was just a normal thing couples do when they reach a certain stage of their relationship."
So after that drama, no wonder Kournikova and Iglesias, the son of an internationally renowned entertainer who's familiar with how nutty the tabloids can get, do not splash their romance all over social media or court more attention than they would naturally receive as a celebrity couple.
"I think it comes with the territory," Iglesias told E! News in March 2014. "I understand why people ask, 'Are you married? Do you have a girlfriend? Do you have kids? Do you have kids that we don't know about?'"
He explained, "When I go back home, I want to make sure that whatever goes on in my house, it's just for me and my loved ones that are with me right there. I need that."
Whether she and Federov ever tried marriage on for size or not, Kournikova and Iglesias had met by the end of 2001. The sexy "Escape" video premiered in January 2002 ("we're trying to get as much sex in this video as possible," Iglesias quipped) and they attended the MTV Video Music Awards together that August.
The stars simply aligned for the Spanish singer and Russian tennis player, both of whom had adopted Miami as their hometown; loved sports, the sun and being on the water; and understood what it was like to be on the road for weeks or months at a time.
Plagued by injuries, Kournikova actually retired from competitive tennis in 2003 (she never won a singles championship but had 16 in doubles, including two Grand Slam titles), though she'd continue to play in exhibitions and other related events for years to come, and she remained one of the most talked-about, for better or worse, athletes in sports.
"I know what it's like to be judged, dissected, picked apart for all of my life," Kournikova told the Los Angeles Times in 2011, when she joined The Biggest Loser as a trainer. "It was so painful. I was just a kid at the time. I was being judged over here for being too pretty, or over there for not looking good enough. And God forbid I gained a pound. I heard about it. And then I was being criticized for not being a good enough tennis player and yet I knew—I knew—I was giving it everything I had."
In 2004 she and Iglesias sparked secret-marriage rumors (denied) and in April 2007 he told People en Español that he wasn't sure if he foresaw marriage, or even happily ever after, for them. "The only thing I can say is that, in my opinion, Anna, whether we are together or not, would be an ideal mother," he said.
The following month he further mystified people, reportedly telling Sweden's Aftonbladet that not only did they break up... "We're divorced. I am single now, but that's okay," he was quoted as saying. "I don't mind being alone."
But Kournikova's rep said the singer had been joking and they were still together after five years of dating. Meanwhile, the athlete did have her own thoughts on the subject, which she eventually became comfortable sharing. "I'm never getting married," Kournikova told People in 2008, but added that "everything is good" on the personal front.
She explained her own approach to trying to maintain her privacy to The Guardian in 2008, saying, "Girls look at him. Guys look at me. It goes with the job, but it gets annoying when you feel violated. Just take the picture and be done.'" You could almost hear the shrug.
"I'm not married, not pregnant, didn't have a boob job, no Botox. What else?" she offered.
That being said, Kournikova wasn't accompanying herself on a tiny violin or anything.
"Hey, I took the money," she said, referring to the perks that came with her tacit agreement to be in the public eye. "It's simple. If you don't want the attention, don't take the money."
Kournikova reiterated on The Graham Norton Show in 2010 that she and Iglesias had no plans for marriage. "We're fine—we're perfect...Being eight years together, it's more [like] being married [than most] Hollywood couples, or whatever." ("Common law now," agreed fellow guest Katy Perry.)
"[Marriage] isn't important to me," she continued. "I'm in a happy relationship—that's all that matters. I believe in commitment. I believe in being open and trusting each other and respecting each other completely."
Finding a like-minded partner is also key.
"I want my personal life to be as private as possible," Iglesias said in an interview with Australia's Today Tonight in 2011. "And especially when you're with someone that's also known and in the spotlight."
"It's not that tough," he added. "You've got to have a sense of humor. I've been married about 28 times, have kids all over the world. In Australia...I think I've got twins in Australia, in Perth. Truly, you just laugh at it." (In 2014, he trotted out the divorce joke again—he must be great at dad humor—when he told reporters in Los Angeles, "I got a divorce three days ago and I wanted to give you guys the exclusive. I'm serious. No, seriously. Don't laugh.")
Meanwhile, marriage apparently wasn't on their to-do list, despite the impressive diamond rings Kournikova started wearing.
"I've never really thought marriage would make a difference," Iglesias told Parade in 2012. "Maybe it's because I come from divorced parents, but I don't think you love somebody more because of a piece of paper."
He reiterated as much to E! News in 2016, though he added cryptically, "Who knows what the future holds...or the past...haha."
The youngest of three born to Spanish super-star Julio Iglesias and his first wife, Maria Isabel Preysler-Arrastía, he has a notoriously prickly relationship with his father, who went on to have five more children with his second wife. Enrique told The Guardian in 2010 that the person he most admired in life was "Elvira, the lady that took care of me when my parents weren't able to be there. She dedicated her whole life to me and my brother and my sister. Now I take care of her."
In 2014, Julio Iglesias told The Mirror that he had never met Kournikova, though he wholeheartedly approved of the match.
"My kids are very independent and it is difficult to see Enrique because he is all over the world," the singer said. "But Anna is very beautiful—they have good taste, my kids."
Iglesias' mother, siblings, stepmom and step-siblings had met her, though, Julio said, and he was confident that his son was doing well. Meanwhile, Igelsias' mom, sister and brother all expressed their excitement when the twins were born three years ago.
"It was a perfectly normal pregnancy, she didn't have to do mandatory bed rest at any time," the babies' grandma Isabel Preysler told Hola! "Anna hasn't had to hide. She has a very simple and homey life."
Iglesias wasn't a regular in the crowd while Kournikova was still playing, presumably not wanting to be a distraction, but they do like to watch tennis together. They were photographed in the stands at the Los Angeles Tennis Center in 2004, and then popped up at what's now the Miami Open, held annually in Key Biscayne, to watch Serena Williams play in 2009.
Asked in 2007 if he could beat his girlfriend at any sport, Iglesias confidently told Sports Illustrated, "Anything except tennis and wrestling. Her reflexes are disturbingly good. You throw anything at her, and she catches it."
Dating an athlete, Iglesias said, had made him respect athletes 1,000-times more. "In music you can start whenever, 18 or 19 years old," he said. "If you want to be an athlete, you have to start when you are 4 or 5. There is so much dedication, so many hours, mentally and physically. Sometimes your mind wants it so much but your body cannot handle it.
"Anna took to me the place where she was brought up in Russia and if you see the house she lived in, you can open up your arms and touch it wall to wall. Out of there, she played every single day for eight hours since she was 5 years old. For me, it's mind-boggling. To me, she is the most amazing person I have ever met."
They've been all over the world on vacation like glamorous celebrities, but part of their charm is that they usually keep date night local like regular people, whether they're catching a Miami Heat game or just going out to dinner, or taking their boat for a spin (that's considered regular in Miami Beach).
In fact, after they were rumored to have broken up in 2013, the inevitable rumor-quashing pictures of them on the boat were forthcoming.
Kournikova also said on The Graham Norton Show that they had their ordinary-couple issues just like anybody else. Asked if Iglesias left his wet towels lying around, she said, "Yeah, and you find underwear, you know, everywhere and dirty socks and everything."
"At least it's Enrique Iglesias' dirty underwear," Norton quipped. "Put it on eBay."
But that's as much dirty laundry as we should expect to hear about firsthand. "I keep my personal life as private as possible because I feel that we need that," Iglesias said on CBS Sunday Morning in April 2014.
Asked about his past comments regarding marriage, he clarified, "I didn't say that I don't want to get married. I don't know if I maybe came out the wrong way. What I said is that, 'We are extremely happy the way we are.' I'm not against marriage by any means."
He continued, "I have not ruled it out, but if you're happy, I don't think it will really make a difference. She's the coolest girl in the world."
Meanwhile, Kournikova embodied the perfect-day scenario he had been describing for nearly a decade.
"A day off for me is being at home on the sofa, watching TV with my girlfriend and our two pets—just having a good time," Iglesias told Ventaneando in October 2017.
Even more telling, he added, "I would love to have children. Hopefully very soon. I think I'd be a good father, my girlfriend would be an even better mother, but I'd be a good father."
The couple had two months to go before their carefully laid plan came to fruition.
"It's incredible to watch her be such a great mother," Iglesias told The Sun in October 2018. "It's incredible to watch a mom do what she does, when a mother's instinct kicks in." And, asked whether becoming parents had put a damper on their alone time, the singer informed the tabloid that "the sex has not diminished."
(Originally published June 7, 2018, at 3 a.m. PT)