Before Duchess Meghan, it was no secret Prince Harry had been romantically linked with some stunning ladies.
What's more, he remained on very friendly terms with them, despite going their separate ways... well, apart from one it seems.
During a recent trip to Amsterdam for the opening of Soho House with his new wife Meghan, the pair mixed with famous friends including Eddie Redmayne and Simon Pegg.
But there was another guest that Harry clearly wasn't prepared for.
According to Vanity Fair, sitting in the same room for breakfast one morning was actress Jenna Coleman, who was romantically linked with Harry back in 2015, before he met Meghan.
An eyewitness told the publication they saw Harry blush when he spotted her.
"Harry had to walk straight past Jenna to get to his and Meghan's table," they said.
"It was pretty awkward and some of the other guests were commenting on it."
Apparently, Jenna looked down while Harry stared determinedly ahead - a classic move.
During the breakfast, Meghan was not fazed, but Harry looked "a bit uncomfortable".
"He'd been super friendly saying hi to everyone, but he didn't even acknowledge Jenna," the eyewitness said.
In June 2015, Harry was linked to the Doctor Who actress after the pair were spotted cosying up at the Audi Polo Challenge, an eyewitness told The Sun.
"From their body language it looked like they were really enjoying each other's company," the onlooker explained.
Whether anything eventuated between the two is uncertain, as Jenna's current boyfriend and Victoria co-star Tom Hughes was understood to be pursuing her at the same time.
The encounter is certainly not the first time the Prince has been in the same place as an ex-flame, but previous situations have been far less awkward.
In fact, his former partners Chelsy Davy and Cressida Bonas were in attendance at Harry and Meghan's wedding in May, having been invited by the Prince himself.
Of all of Harry's past girlfriends, his on-again-off-again relationship with Zimbaween blonde beauty Davy is his most renowned.
The pair ultimately ended things in 2011 following the royal wedding between Prince William and Duchess Catherine. This was the reason for the break-up, according to journalist Angela Levin.
"A friend revealed that seeing the enormity and pomp of the day convinced Chelsy that she and Harry had been right to separate," Angela wrote in her royal 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."
Chelsy, who left her legal career to become a jewellery designer, spoke to The Times in 2016 saying she found the spotlight to be "crazy and scary and uncomfortable".
"It was so full-on: crazy, and scary, and uncomfortable. I found it very difficult when it was bad. I couldn't cope."
Despite the breakup, Chelsy said they would always be good friends, which she was clearly right about.
As for his two-year relationship with Cressida which followed, it was reported the pair ended things for similar reasons with the blonde struggling to deal with the attention on the royal family.
While it's unknown exactly what happened between Harry and Coleman, it's clear the two aren't on the same friendly terms as Chelsy and Cressida!
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