If you’re a fan of 2000s nostalgia, you definitely remember the era of the "low-key" celebrity romance. Before Instagram and TikTok turned every date into a staged event, Ashley Olsen and Matt Kaplan were the blueprint. They were young. They were successful. And honestly, they were surprisingly normal for a pair of teens navigating the height of "Olsenmania."
Fast forward to 2026, and their names are still frequently searched together. Why? Because both have gone on to become massive power players in their respective industries, albeit in very different worlds. Ashley is the reclusive force behind The Row, and Matt is a Hollywood mogul who recently dominated headlines with his high-profile marriage to podcast giant Alex Cooper.
But their story started way back in 2001.
The Early Days: More Than Just a Teenage Crush
People often forget how young Ashley was when she met Matt. She was 15; he was 17. Mary-Kate Olsen actually takes the credit for this one. In a 2003 interview with Rolling Stone, Mary-Kate admitted she was the one who introduced them.
Kaplan wasn't just some random guy. He was a star quarterback at Columbia University. For a girl who spent her life under a microscope, dating a college athlete felt grounded. Ashley once famously described their relationship as "pretty boring." They’d go to the movies. They’d grab dinner. It wasn’t the glitzy Hollywood lifestyle the tabloids expected.
They stayed together for three years. In teen years, that's an eternity.
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Why Did They Break Up?
The split happened in 2004. There were no dramatic cheating scandals or "insider" leaks about toxic behavior. According to their reps at the time, it came down to the classic killer of young love: distance. Ashley was busy building a fashion empire and dealing with the transition out of acting, while Matt was focused on his life at Columbia.
"It's been hard," Ashley told People shortly before the breakup. "A long-distance relationship is tough, no matter what."
They called it quits amicably. Honestly, looking back at 2026 standards, it was a remarkably clean exit for two people who grew up in the public eye.
Where Is Matt Kaplan Now?
If you don't recognize the name Matt Kaplan from the football field, you definitely know him from the closing credits of your favorite Netflix movies. He shifted from sports to cinema, eventually becoming the CEO of Ace Entertainment.
He’s the guy behind:
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- The To All the Boys I've Loved Before franchise
- The Perfect Date
- XO, Kitty
Basically, if it’s a Gen Z rom-com that made you cry, he probably produced it.
His personal life has been just as buzzy. After a brief marriage to Vampire Diaries star Claire Holt (which lasted about a year), Matt found himself in the middle of a media whirlwind when he started dating Alex Cooper, the host of Call Her Daddy. For years, she called him "Mr. Sexy Zoom Man" to keep his identity a secret. They finally tied the knot in April 2024 in a massive ceremony in Mexico.
Ashley’s Quiet Evolution
While Matt has stayed in the Hollywood spotlight, Ashley Olsen took a sharp left turn. She famously quit acting to focus on The Row with Mary-Kate. In 2026, she’s widely considered one of the most respected figures in luxury fashion.
She also found her "forever." In December 2022, Ashley secretly married artist Louis Eisner in a private Bel-Air ceremony. They had only about 50 guests. No paparazzi. No "leaked" drone footage.
In 2023, they welcomed their first child, a son named Otto. Much like her relationship with Matt Kaplan decades ago, Ashley keeps her family life extremely shielded. She and Louis made a rare red carpet appearance in September 2025 for the YES Scholars 25th Anniversary Gala, looking every bit the sophisticated New York couple.
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Why We’re Still Talking About Them
It’s rare to see a teenage couple where both individuals go on to reach the absolute top of their fields. Usually, one person fades into obscurity. Not here.
Matt Kaplan became a titan of young adult media.
Ashley Olsen became a titan of high fashion.
They represent a specific moment in time—the transition from child star to adult professional.
What You Can Learn from Their Trajectory
- Privacy is a choice. Ashley proved you can be a billionaire and still have a private life if you’re disciplined about it.
- Professional pivots work. Matt went from a quarterback to a producer; Ashley went from a sitcom star to a designer. Your first career doesn't have to be your last.
- Amicable splits are possible. You don't always need a "villain" in a breakup story. Sometimes, you just grow apart.
If you’re tracking their current moves, keep an eye on Ace Entertainment’s upcoming slate for 2026—Kaplan is reportedly expanding into more "unscripted" territory. For Ashley, expect to see The Row continue its dominance in the "quiet luxury" space, likely with new flagship openings in Europe.
Next Steps for Deep Research:
- Check the latest SEC filings for Great Elm Capital Corp if you're interested in Matt Kaplan’s business holdings.
- Review the 2025 YES Scholars Gala photos for a look at Ashley’s current style evolution.
- Listen to the April 2024 episodes of Call Her Daddy for Alex Cooper's firsthand account of her wedding to Kaplan.