What Really Happened With Meghan Markle and Trevor Engelson

Before the tiaras, the Netflix deals, and the global scrutiny of the House of Windsor, there was a girl in a yellow bikini on a beach in Jamaica. She was playing "wheelbarrow" with her friends. That girl was Meghan Markle, and the man holding her legs was her new husband, Trevor Engelson.

It’s easy to forget that the Duchess of Sussex had a whole life—a whole decade, basically—with another man before Prince Harry ever entered the frame.

Meghan Markle and Trevor Engelson were together for nine years total. That’s a long time. People tend to treat their marriage like a blip on the radar because it only lasted two years on paper, but they started dating way back in 2004. He was an aspiring producer; she was a struggling actress trying to get more than a two-line part on a procedural drama. They were a Hollywood power-couple-in-training.

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Honestly, their story is less about a royal fairy tale and more about the brutal reality of how ambition and distance can absolutely wreck a relationship.

The 2004 Dive Bar Meet-Cute

They met at a bar. No curated "blind date" set up by a mutual friend in London. It was West Hollywood, 2004. Meghan was 23. Trevor was 28.

According to Andrew Morton’s biography Meghan: A Hollywood Princess, they were both hustling. Trevor was starting his production company, Underground, and Meghan was doing the grueling circuit of auditions. They were a match. They lived together for years, building a life in a small Los Angeles home long before the world knew her name.

Trevor actually helped her out early on. He was the producer on the 2010 Robert Pattinson film Remember Me, and if you look closely, you’ll see Meghan in a tiny role as a barmaid named Megan. He was her biggest cheerleader.

Then came 2011. The year everything changed.

The Jamaica Wedding and the Marijuana Rumors

In September 2011, they headed to the Jamaica Inn in Ocho Rios. It wasn't stuffy. It wasn't "royal." It was a four-day party for about 100 guests.

There’s been a lot of talk about that wedding. Meghan’s own father, Thomas Markle, claimed in interviews later that guests were given small bags of marijuana as party favors. At the time, it was illegal in Jamaica, though as Thomas put it, "customary." Whether that's true or just tabloid fodder, the vibe was clear: laid-back, bohemian, and very "Hollywood elite on vacation."

Meghan wore a strapless white dress with a sparkly silver belt. She looked happy. But here’s the kicker: she had just landed the role of Rachel Zane on Suits.

The wedding happened, and almost immediately, the "happily ever after" hit a massive, 2,500-mile-long wall.

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Why the Meghan Markle and Trevor Engelson Marriage Collapsed

The problem wasn't a lack of love. It was geography.

Suits filmed in Toronto. Trevor was based in Los Angeles. While Meghan was becoming a star in Canada, Trevor was back in California running his business.

• The Distance: They were living separate lives. Meghan was suddenly part of a hit show, going to high-profile parties in Toronto, and finding her own voice.
• The Power Shift: For years, Trevor was the "successful producer" and Meghan was the "struggling actress." Suddenly, she didn't need his help anymore. She was the one in the spotlight.
• The "Out of the Blue" Split: By August 2013, it was over.

There’s a famous story—vouched for by Meghan’s former best friend Ninaki Priddy—that Meghan ended things so abruptly she sent her diamond engagement and wedding rings back to Trevor via registered mail.

Trevor was reportedly blindsided. Friends of the producer have told outlets like The Daily Mail that he went from "cherishing Meghan" to feeling like "a piece of something stuck to the bottom of her shoe." He was hurt. Deeply.

The "She'll Close" Comment

For years, Trevor Engelson has been the "silent ex." He hasn't done the tell-all interviews. He hasn't written the book (though rumors of a memoir or a TV show inspired by his life have swirled for years).

But there is one specific quote that made waves. Bethenny Frankel, of Real Housewives fame, once mentioned that she briefly dated Trevor after the divorce. When news broke that Meghan was dating Prince Harry, Bethenny reportedly texted Trevor to ask if he thought Meghan would actually marry the Prince.

His response? "Oh, she'll close."

It’s a very "producer" way of saying she’s a closer—someone who gets what they want. It wasn't necessarily an insult, but it gave a glimpse into how he viewed her ambition.

Where Are They Now?

Both have moved on, though their lives couldn't be more different.

Meghan, obviously, is the Duchess of Sussex, living in Montecito with Harry, Archie, and Lilibet. She’s become a global icon, a lightning rod for controversy, and a media mogul in her own right.

Trevor also found his happy ending. In 2019, he married Tracey Kurland, a nutritionist and heiress to a multi-million dollar fortune. Funnily enough, they also live in California—not far from the Sussexes. They have children now, and by all accounts, Trevor is thriving in the industry, having produced hits like the FX series Snowfall.

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He seems to have no interest in being "the ex-husband" forever. He's just Trevor.

What We Can Learn From Their Story

Relationship experts often point to the Markle-Engelson divorce as a classic case of "growing apart." When one partner experiences a massive shift in status or career (like landing a lead role on a TV show), the old dynamics of the relationship often break under the pressure.

If you're looking for a takeaway, it’s basically this: Ambition is a double-edged sword. The same drive that made Meghan a star and a Duchess was the same drive that made her Los Angeles life with Trevor feel too small.

If you want to understand the Duchess of Sussex today, you have to look at the years she spent in the trenches of Hollywood with Trevor. It’s where she learned the business, where she found her confidence, and where she decided that "good enough" wasn't enough.

Actionable Insight: If you're navigating a long-distance relationship or a major career shift with a partner, communication about your "new" roles is vital. The "registered mail" approach to ending things is generally not recommended if you want to keep your reputation—or your friendships—intact.

Research the timeline of Meghan's move to Toronto to see exactly how the "Suits" schedule overlapped with her marriage for a clearer picture of the breakdown.