#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time. 

By Isabel Jones
Apr 11, 2019 @ 5:30 pm

Who: British prince currently fifth-in-line to the throne, Prince Harry, 34, and South African jeweler and businesswoman, Chelsy Davy, 33.

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How They Met: Davy and the red-haired royal reportedly met during his gap year in 2004.

When They Peaked: This 2006 photo is the perfect distillation of what we imagine it was like to be young, extraordinarily wealthy (Davy’s father is a millionaire “safari farmer” in Zimbabwe), and “madly in love” before the dawn of the smart phone. The then-20 and 21-year-olds enjoyed “Cartier International Polo Day” (does it get bougier than that?) while leaning against an Audi and sipping from tiny bottles of mineral water and Red Bull.

Harry wore a pair of Matrix-style shades, which he no doubt received several compliments on, while Chelsy opted for a more oversize, Victoria Beckham-esque style, which she complemented with a set of the sort of shoulder-grazing button-and-feather earrings that Claire’s specialized in. Adding a touch of whimsy to what is otherwise a portrait of early-aughts privilege, the Prince allowed a swath of his neon pink-striped socks to peek out from his brown loafers.

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No guarantees, but we’d like to imagine they spent their post-Polo hours downing “vodka-and-cranberry drinks and shots of Sambuca” and partying into the wee hours of the morning — that seems to have been their thing.

Why We Loved Them: After reuniting ahead of Prince William and Kate Middleton’s 2011 wedding, the pair, about 7 years into their on-and-off-again relationship, tried to keep a low profile. So they did what any couple dodging the spotlight would do and left a London club after a night out by allegedly hopping into the trunk (!) of their car (which happened to be a Jaguar, natch), thereby no doubt attracting 1,000-times the media attention they would have if they’d just opened a door. This blend of caution and extravagance feels like a genuine metaphor for their drawn-out relationship.

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The Breakup: Which one? The couple split several times for various reported reasons: differing schedules, missed birthdays, a reported visit to a lap-dancing club

A royal phone-hacking in 2006 revealed that Harry would drunk-dial his girlfriend often, which isn’t always too charming — even when said drunk caller is a legitimate prince. On that same note, said hacking also unearthed a hilarious prank call from Prince William in which he impersonated Davy’s voice and said, “Hi, it's Chelsy here. You're the best looking ginger I've ever seen . . . You big hairy fat ginger.” What I would give to hear it with my own ears …

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Anyway, after years of breaking up and making up, Chelsy and Harry ultimately ended things after Will and Kate’s royal wedding in 2011. “Seeing the enormity and pomp of the day convinced Chelsy that she and Harry had been right to separate,” journalist Angela Levin wrote in her biography Harry: Conversations with the Prince. "Although they had a lot in common, she saw clearly that because they came from such different worlds it could never have worked, especially as she valued her privacy and guarded it so carefully," she continued.

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Davy herself echoed that sentiment during a 2016 interview with The Times. “It was so full-on: crazy and scary and uncomfortable,” she said of the media attention surrounding her relationship. “I found it very difficult when it was bad. I couldn’t cope.”

Where They Are Now: Davy is rumored to be dating British TV producer James Marshall, whose ex-wife Elettra Rossellini Wiedemann just, uh, happens to be an old pal of Meghan Markle (who, I don’t know if you’ve heard, is married to Prince Harry). Coincidence? Probably, but a Markle-orchestrated set-up is way cuter.

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Harry and said wife Meghan haven been married for nearly a year now (Davy was present at their May 19 wedding) and are expecting their first child any day now.

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