The following article includes mentions of suicide.
Who would the young prince end up with?
Many assumed Zimbabwean-born socialite Chelsy Davy would bag the royal ring since the pair had been dating since 2004.
When he stepped out with the quirky London-born entertainer, the tabloids had a lot to say.
The romance may have been short-lived, but it certainly left a lasting impression on both of them.
As for Harry, he didn’t scrimp on the details, either.
He dubbed the brief tryst “tainted” in his memoir, “Spare.”
So, what exactly happened between the royal and the late “Love Island” host?
What was it about this affair that made it so memorable for both of them?
Let’s dig into the details.
Princess Diana had several A-list friends, spanning from Tom Hanks to Elton John.
King Charles III also has quite the inner circle, counting Rod Stewart as one of his pals.
However, Harry and Flack shared acquaintances.
By the time they met in 2009, Davy and Harry’s situation was on again, off again.
Things were a lot different for Harry, who grew up under the watchful gaze of the entire world.
Caroline and Harry later spoke about how much fun they had in the early days of their whirlwind courtship.
At the time, Harry was known for being a partier.
Flack was also enjoying her time in London’s social scene.
In 2009,Marie Clarereported that one of their dates included a boozy night out at Troubadour in Fulham.
They reportedly left together at 4 a.m. when they were driven back to Clarence House by Harry’s bodyguard.
The news got out
The British tabloids seem to have a sixth sense for new royal romances.
Every senior member of theroyal family has had their love life scrutinizedunder the microscope at some point.
Prince Harry was no exception.
It didn’t take long for the paparazzi to snap pictures of Harry and Caroline Flack together in London.
And just like that, it went from an under-the-radar romance to a very public matter of interest.
AsMeghan Markleknows, dating Prince Harry isn’t for the faint of heart.
It takes a particular jot down of person to put up with the invasiveness of the British press.
Almost immediately after the news of their relationship broke, photographers gathered.
As Harry explained in “Spare” (viaYahoo!
It didn’t just stop there, either.
Of the press' reaction, he wrote in his memoir (viaHello!
): “Are we really such a country of insufferable snobs?”
The media had even gone so far as to call Flack “Prince Harry’s bit of rough.”
Caroline later detailed how her public persona changed after things went stratospheric.
“I was no longer Caroline Flack, TV presenter, I was Caroline Flack.
Prince Harry’s bit of rough,” she wrote in her memoir (viaUs Weekly).
“Once the story got out, that was it.
We had to stop seeing each other.”
It wasn’t long before the couple ultimately decided to part ways.
Were there any hard feelings?
When royal romances end, it’s a huge deal.
Obviously, when Prince Harry and Caroline Flack split, it wasn’t the ideal outcome for their relationship.
But did Harry and Flack actually manage to salvage a friendship out of the whole circus?
However, it seems like it ended pretty amicably.
That’s when things got really interesting.
Caroline Flack was still finding her feet in the industry in 2009.
Producers liked her style and audiences warmed to her vivacious bubbly personality.
Career-wise, things were looking up for Flack.
She wasn’t a total unknown anymore or “that girl from the TV.”
She was Caroline Flack, the woman that hosted some of Britain’s biggest television shows.
In an incredibly competitive industry, this wasn’t something that was easy to achieve.
Flack’s natural charisma helped her beat her way to the top.
“I loved Chels' ease … She didn’t care what anyone thought.
I couldn’t help what my grandmother thought about it.
… And the last thing I wanted was for Chels to change to yo them.”
Flack went on to have a very highly publicized and controversial romance with Harry Styles.
At the time, Harry was just 17 while Flack was 31.
Just like her royal relationship, this entanglement seemed to be doomed from the beginning.
“I’ve never felt I was much older than Harry.
I still feel 18 and I probably act that way half the time.
Tragically, her own love story with Lewis Burton would be her last.
The pair had been dating for some time when an altercation resulted in the police being called.
While reports of the events are varied, Flack was charged with assaulting Burton.
I can’t comment further on these matters until the legal process is over” (viaThe Guardian).
Two months later, Flack was found dead in her home on February 15, 2020.
Flack’s former agent, Alex Mullen, wasn’t very happy about Harry’s mention of her.
Mullen had worked with Flack for years, right up until her untimely passing in 2020.
Even though Prince Harry spoke highly of Flack, Mullen felt that it was in poor taste.
“Gross for Prince Harry to reveal such private details about Caroline Flack.
For a start, 2009 was a time of major change within the media landscape.
Like Flack, Meghan wasn’t the sort of polished and aristocratic debutante royalists envisioned Harry marrying.
For Harry, it was a warning shot that love was never going to be easy for him.
Harry and Meghan would go on to wage their own battles with the British press and emerge triumphantly.
Something tells us Caroline Flack would’ve been cheering on from the sidelines.
