While Anne was regularly seen at royal functions and horse events in her younger years, one of the first men ever linked to the daughter of Queen Elizabeth was Gerald Ward - who would later become Prince Harry's godfather.
The soldier, banker, businessman, farmer and sportsman was regularly spotted with the princess shortly after she left Benenden school in her late teens. While the couple never confirmed their romance, it’s been claimed in several reports since that they shared a close bond at the time.
Shortly after, Anne was romantically linked to horseman Richard Meade - who went on to win 3 Olympic gold medals for eventing.
His children are very close friends of Prince William and Harry, with William naming them among Louis' godparents.
Then, came Princess Anne's most scandalous romantic past.
Andrew Parker-Bowles, the ex-husband of Camilla Parker-Bowles, had a heated love affair while he was dating the Duchess of Corwall, royal writer Penny Juror claims.
Throughout the years, the former British Army Officer's extramarital affairs become somewhat notorious, after he married Camilla Shand - now Duchess of Cornwall - in 1973.
Royal writer Junor believes that Camilla may never have struck up a romance with Prince Charles if her then-boyfriend hadn't struck up an affair with his royal sibling.
Junor, who regarded as a reliable source, claimed that Camilla planned to teach her 'cheating boyfriend a lesson.'
She recalled the love affairs during a talk at the Henley Literary Festival, stating: '[Camilla] was passionately in love with [Andrew] but he was a cad, he was bonking other people, some of her friends.
'There was a lovely story when she was walking through London in the evening and spotted his car parked outside the flat of a very good friend of hers. So she let the tyres down and wrote a message in lipstick on his windscreen.
'So when she was introduced to Charles and he thought she was pretty special...he thought she was a bit of alright and she thought 'Andrew is at the moment off with Princess Anne, you know her brother, teach Andrew a lesson'. So she had a fling with Charles.'
Fellow royal writer Phil Dampier believes Junor's story may be true, and knowns that Parker-Bowles and Princess Anne are very close friends.
He told IBTimes UK: 'I have read this before and it wouldn't surprise me. Anne and Andrew Parker Bowles were very close – and they still are!
'You see them together at Royal Ascot every year and they are best friends. He was her first love and their bond goes very deep. It was a weird royal set-up which Diana went into not realising the depth of the relationships.'
Anne went on to marry Captain Mark Phillips, just four months after her affair with Andrew ended.
According to the Mail Online, a palace insider claimed at the time: 'She was in pieces over Andrew’s marriage to Camilla. But she’s made of stern stuff — she sought out and found a Photofit of Andrew, and married him.'
Following a stunning wedding attended by the royal family, they enjoyed a 19-year marriage and welcomed son Peter and daughter Zara together.
However, despite the image of a perfect marriage, the rumours began for Anne.
Anne was hit with reports that she had struck up a romantic love affair with her personal bodyguard, Sergeant Peter Cross of the Royal Protection Squad.
It's claimed that Cross was relieved of his royal duties shortly after.
He later sold his story to UK newspaper, News Of The World, in 1984 for a reported £600,000 (AU$1million), said to be the equivalent of around $2million today.
In it, Cross made claims that he and the princess would 'snuggle up together in front of the TV' and that she would ask him to come to the country side for days on end. Cross' claims were never confirmed.
Anne later became involved with current husband Timothy Laurence.
While he was unmarried at the time, letters between the pair were leaked to another UK newspaper shortly after.
They married shortly after in December 1992, eight months after her divorce from Phillips.
The couple have been together ever since and while they keep their private life largely out of the spotlight, they’re often spotted together at public events and royal engagements.