Anna Kournikova and Enrique Iglesias's Relationship Spans Two Decades

You might be surprised to learn that Latin pop heartthrob Enrique Iglesias has been in a committed relationship with the same woman for over two decades. Yep, Anna Kournikova and Enrique first crossed paths in 2001 when she starred as his love interest in the music video for his hit song "Escape." Funny enough, the "chemistry" they had to fake for the cameras turned into the real deal, and they started dating shortly after.

It must’ve been fate, because these two have been going strong ever since, welcoming three beautiful kids together. And let’s be real — given how long they’ve been together, you can bet a lot has gone down between that first meeting and now. So, let’s take a look at their relationship timeline and some of their most unforgettable moments they've shared over the years.

Anna first met Enrique in 2001 at the age of 20, and just a short time after that steamy makeout session in the "Escape" music video, the two went on to date. By 2002, they made their public debut as a couple, stepping onto the red carpet together.

Fast forward to 2004, and engagement rumors started swirling when Anna was spotted at a tennis match sporting a massive pink diamond ring. While fans were buzzing about a possible proposal, it turns out they never officially got engaged — it may have just been a promise ring. And here’s another fun fact: Enrique and Anna have never tied the knot.

In May 2003, at just 21 years old, Anna made the tough decision to retire from tennis after a series of injuries. Having started playing at the age of 5, it seems Anna's life took an unexpected turn after meeting Enrique. She even shared a nostalgic throwback photo on Instagram in 2016, giving fans a glimpse into her early tennis days.

Although Anna and Enrique were clearly thriving as a couple, when asked about marriage, Anna made her stance clear in an April 2008 interview with People, saying, "I’m never getting married." And it looks like she’s stayed true to her word — more than two decades later, the couple is still going strong, proving that their bond is unbreakable, even without a wedding ring.

After being together for nearly 16 years, Anna and Enrique decided it was time to take their relationship to the next level — parenthood. Their first go-round resulted in twins, Nicholas and Lucy, who are now 7 years old. The couple managed to keep the pregnancy under wraps for a while but eventually shared sweet photos of their babies in January 2018, giving fans a glimpse into their growing family.

Anna and Enrique expanded their family even further in early 2020 with the arrival of their daughter, Mary. Just a month after her birth, Enrique took to Instagram to share a truly intimate moment — posting a photo of baby Mary literally moments after she was born via C-section.

Since expanding their family, Anna has shared various sweet moments from their family life together, and it’s clear she’s fully embracing the mom life. Whether it’s cute photos or heartfelt updates, she’s all in on this new chapter.

As for Enrique, fatherhood suits him well, but he's still busy making music and staying active in the industry, proving that he’s a dedicated dad and artist all at once.