For Prince Harry, Chelsy Davy was always the one that got away. But spare a thought for the Duchess of Cambridge, who was also incredibly close with her brother-in-law’s long-term girlfriend – and was said to be “absolutely devastated” when the pair broke up for good in 2011.
WATCH: Chelsy Davy watches on as Prince Harry marries Meghan Markle
“Kate and Chelsy were thick as thieves,” shares a source. “They always attended events together when they were dating William and Harry.”
As they navigated the choppy waters of royal life, Chelsy and Kate were often seen sticking to each other like glue at parties, weddings and polo matches, preferring to enjoy their own company rather than spending too much time with the “society snobs” that attended these events.
“At the time, Kate quietly thought Harry made the biggest mistake of his life in letting her go,” says the source.
Despite Chelsy, now 36, ending things with Harry, insiders say she has remained on good terms with Kate, 40.
“They’ve stayed in touch over the years,” says our source. “Kate was delighted to see Chelsy at Harry’s wedding. And given things were already tense with [his bride] Meghan Markle, she must have had a tinge of wistfulness about what could have been if he’d married Chelsy.”
Considering their years of happy memories, it’s no wonder that, according to insiders, Kate and Zimbabwean-born Chelsy have recently reconnected.
“Chelsy runs a luxury Africa travel service, and William and Kate are hoping to plan an epic joint 40th birthday trip there,” says the source.
Wills’ big day is in June, while Kate had to postpone her own 40th celebrations in January due to a new wave of COVID cases.
“After that, Kate reached out hoping Chelsy could help plan something amazing,” says a source. “Chelsy has a lot of time for Wills and Kate – after all, there was a time in her life when she assumed they’d be her brother and sister-in-law. She would’ve been thrilled to assist.”
Sources say Chelsy divides her time between Africa and the UK. There are whispers she’s been catching up with Kate in person to help her plan the trip, but no doubt Harry has also been a topic of conversation over a glass of wine and dinner.
Indeed, in the 11 years since Chelsy split from Harry, 37, over the relentless spotlight on their five-year relationship, there’s been plenty to catch up on.
“There aren’t many people in the world who know Harry as well as Chelsy does, and even she’s noticed a dramatic change in him since he met Meghan,” says the source. “He no longer seems like the cheeky guy she fell in love with, who was close to his family.
“She doesn’t know this moody man, who moved overseas to make barbed comments about his brother and father in the media.
“Even though they’re long over, Chelsy will always love him and she’s concerned about him. Catching up with her old friend Kate to get the real story is long overdue.”
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