Prince Harry and Chelsy Davy's Breakup Showed Me Love Doesn’t Always Conquer All
Sometimes, it leads you to something new — something that's truly meant to be.
When Kate and William wed in 2011, I was 19 years old and fascinated with all things Royal Wedding. I taped the live, six-hour event and kept the footage on my DVR for years. I used to watch it late at night when I couldn’t sleep; a real-life fairytale wedding can be a strange, soothing device for a single heart.
I also remember getting stuck on one clip in particular: a shot of Prince Harry’s ex, Chelsy Davy, walking into Westminster Abbey, clad in teal, blonde hair breezily pulled back under her lace fascinator. I’d seen hundreds of photos of her through the years, laughing with Harry at sporting events and sitting on the grass while he played polo. She was still smiling at the wedding, looking vaguely unsure, but also comfortable. It was a homecoming of sorts. Chelsy had been in similar situations countless times before. She was the seasoned royal girlfriend, just like Kate had been before her.
I loved Harry and Chelsy together. They were the carefree, silly counterparts to straight-laced Will and Kate, both of whom seemed to value privacy over the privilege of going out and about. When Chelsy and Harry broke up in 2009, I never really thought it was a forever-breakup. Surely, the Royal Wedding was the moment they’d reunite, right? During one of the biggest global occasions of the new century, where nearly three billion pairs of eyes would be on him, Harry had asked Chelsy to come support him. It seemed like they just couldn’t quit each other, so they had to get back together. Eventually. Someday. I liked the delusion that their love would eventually triumph.
It was reported that the relationship ended because Chelsy did not want to marry into “The Firm,” as Diana used to call it, and have her life disrupted. “She valued her privacy and guarded it so carefully,” a friend reportedly told Angela Levin, author of Harry: Conversations with the Prince. Chelsy once called the press attention she received with Harry “scary and uncomfortable,” which is one of the apparent reasons she fled back to South Africa. “I found it very difficult when it was bad. I couldn’t cope,” she once said.
But Chelsy seemed like Harry’s person. She was always there for him, even in their broken-up periods; she reportedly even helped him craft his best man’s speech over the phone for Kate and William’s wedding.
Rationally, I knew love didn’t always conquer all, but I had yet to accept that emotionally. When love has only existed in your mind, it’s easy to believe happy endings are common and inevitable when the reverse is actually true. So, I tucked their relationship into the back of my mind, expecting their paths would eventually intertwine. I missed the realization that they were probably not ever getting back together while I was living my own life and learning for myself that even good relationships don’t last forever.
In the years that followed Kate and William's wedding, I would have multiple on-off, bumpy relationships —as well as my first serious relationship. We were in love at the time, despite our five-year age and life experience gap and starkly contrasting personalities — he, an empathetic extrovert, and me, a serious-minded introvert. But our minds worked in tandem. I was scared that staying together meant I’d stay in his shadow, perhaps forever, but I was also scared to lose him.
I remember our three-hour phone call exhaustively discussing the odds that we’d get back together if we broke up. He did not think we ever would, and was against it. I was nervous, but still an optimist. It didn’t make sense to be together now, but in the future, just maybe; believing in that maybe gave me the courage to roll the dice.
We had a clean breakup, but after we split in 2014, we still connected in the years that followed when we needed comfort, support, or someone who just gets you in the way only a person who has watched you grow into an adult really can. We were often single, and not dating (each other, or anyone), but became each other's shoulder to cry on when things got challenging. I always felt inspired after talking to him, the way he’d walk me through my own hairy problems. He was this person I kept coming back to like an old habit. Not a bad habit; just a familiar one.
And then, I started dating my now-fiancé in 2017, and it became apparent how well we fit together, how happy I was. There was an ease between us. I spoke less and less with my ex. When I got engaged in late 2019, that was it. My ex and I stopped speaking entirely. I didn’t really know how to tell him, or what to say, so I didn’t say anything. Sometimes, I wonder if that was right or wrong.
In October 2016, word leaked that Prince Harry had been dating Suits actress Meghan Markle and was “happier than he’s been for many years.” Just days later, it would become apparent how true that was when he made a formal statement defending Meghan against the press’s cruel treatment. I remember being fascinated, a little stunned, still half expecting one day to see a surprise announcement that Harry and Chelsy were set to wed. Looking back through the lens of experience, it’s easier for me to see now that the writing was on the wall a long time ago. But that didn’t mean Harry and Chelsy's relationship wasn’t real, important or full of love. The exes reportedly even had a final phone call the day before he married Meghan to close the chapter. Then, Chelsy put on the bravest face ever the next morning, arriving at Windsor Castle to support the man she once loved as he married someone else. It was bittersweet to witness.
Today, Harry and Meghan are a happily-married, iconic power couple who are daring to forge their own path together, and Chelsy is seeing someone with whom she’s “quite taken,” while living in South Africa designing jewelry. “Everything is falling into place,” she said earlier this year.
Some people are an integral part of your journey, even though the love isn’t meant to last. It’s also a beautiful thing to use old relationships as a springboard to growth — even if you’re propelled in different directions.
Breakups That Broke Us is a weekly column about the failed celebrity relationships that convinced us love is dead.