The Royal Rivalry That Captivated the World: The Untold Story Behind Prince William's Heart
Explore the fascinating tale of Prince William's romantic journey, featuring his most intriguing relationships and the woman who stood as his greatest rival before Kate Middleton.
Unlike Meghan Markle, who often appeared alongside Prince Harry's former loves at public events, Kate Middleton's path was marked by a different kind of rivalry. Before Kate, Prince William had several official girlfriends, but only one was ever considered truly formidable — Jessica Craig.
Before meeting Kate Middleton, Prince William was known as a charismatic and popular figure among women, reciprocating their affections with ease.
Today, most of his former partners — from the young aristocrat Rose Farquhar to Arabella Musgrave, former head of PR at Gucci — have settled into family lives and away from the media spotlight. Except for one: Jessica Craig. She is often referred to as William's first great love and the woman Princess Catherine reportedly could not tolerate.

We can understand Kate’s feelings. Jessica was the woman who stood between her and William for several years, the one he returned to during their 2007 breakup, and, according to some media reports, the mother of an alleged illegitimate son of the prince. Yes, the story has its twists! But let's start from the beginning.
Who is Mrs. Jessica Craig?
Jessica Craig, affectionately known as 'Jezza' by the British press, is a fourth-generation descendant of a family that emigrated from the UK to Kenya in the early 20th century. Her great-grandfather established a calf-rearing farm there, which her family successfully expanded. Jessica's father founded a vast wildlife conservancy spanning over 20,000 hectares — the very place where she met the heir to the British throne.
At 16, William visited Kenya with Prince Charles, who was friends with Jessica's family patriarch. William immediately noticed the slender brunette and stayed close to her throughout his two-week stay in Africa. Their long walks and conversations under breathtaking sunsets created memories that lasted a lifetime. Upon returning to London, where Jessica attended the same university as William, their connection continued to grow.
The Battle for the Prince: Kate vs. Jessica
William met Kate Middleton in 2003. However, Kate did not become his official girlfriend immediately; she had to contend with her main rival, Jessica Craig, who was part of William's inner circle and considered the prime contender for his heart.

Despite the seriousness of William's relationship with Kate, which went beyond friendship, it ended in a breakup. Jessica preferred life in Africa, away from the intense media scrutiny. This cleared the path for Kate, but William did not sever ties with Jessica.
Even while dating Miss Middleton and moving into a separate cottage near university, William found reasons to meet his former love and even celebrated New Year's with her.
Family members urged William to choose the modest Kate. In March 2004, he introduced her to his father, signaling a serious commitment. Yet, his connection with Jessica persisted. In fact, the young and inexperienced prince attempted to introduce his two beloved women to each other, hoping they could spend time together — an experiment that, unsurprisingly, ended poorly.
Like Father, Like Son
This complicated love triangle sparked rumors at court, with whispers that William was following in his father Charles's footsteps — intending to marry one woman while still loving another.
Events seemed to confirm these speculations. William dated Kate but remained close to Jessica. When he and Kate broke up in 2007, William was first in Jessica's arms. They even attended her brother’s wedding together, an event William chose over his cousin Peter Phillips’s ceremony.
Months later, William realized Kate was the one he truly wanted. He returned to her and, in 2010, proposed. The proposal, however, came with its own surprise.
William chose to kneel and present the ring at Jessica's home in Kenya, where the couple was vacationing — a move that the press quickly linked to Prince Charles's proposal to Diana in a garden belonging to Camilla, adding a layer of royal intrigue.
The media couldn't help but draw parallels, calling it an uncanny and somewhat unsettling coincidence.
After their world-famous wedding on April 29, 2011, William continued to meet Jessica. Every encounter made headlines with warnings like 'Watch out, Kate!' The message was clear: former lovers never truly disappear.

In 2014, William left his wife and one-year-old son to attend a press conference in Madrid, where he unexpectedly reunited with Jessica and went on a hunting trip with her. Readers of Woman.ru commented, "Every Windsor has their Camilla," highlighting the ongoing comparisons to Charles and Camilla's relationship.
These meetings became less frequent after Jessica announced her engagement to Jonathan Bailey, a biology professor much older than her, in 2015. The couple had known each other for years and appeared more like good friends than passionate lovers. Yet, only William seemed capable of stirring strong emotions in Jessica.
The Rumors of an Illegitimate Son
Jessica and Jonathan planned their wedding for March 26. William, invited early, promptly booked his ticket to Kenya, surprising his wife, father, stepmother, and beloved grandmother.
His trip meant missing Easter, a sacred tradition for the British royal family, especially significant as it was the first for little Princess Charlotte, who was just 10 months old. Despite this, William prioritized the journey, citing conservation work as the reason for his four-day absence.
However, journalists uncovered a more sensational story.
According to the British Daily Mail, Jessica gave birth to a son four months before her wedding, sparking speculation that William might be the father.
No official proof supports this claim; the theory stems mainly from the secrecy surrounding Jessica's pregnancy. Although a private person, her connection to the heir to the British throne naturally attracted media attention.
Kensington Palace declined to comment, but one can imagine the impact such rumors had on Kate.
Royal-Level Trolling
On May 1, 2016, British Vogue unveiled its June issue featuring Kate Middleton on the cover — a surprising move since she had declined magazine shoots for five years since her wedding.
After the initial shock, the public noticed her unusual outfit: a white shirt, brown suede jacket, and dark green fedora — styles she rarely wore, except perhaps during university days.
A Stylish Message
While Vogue explained that Kate wanted to appear as an ordinary English provincial woman rather than in glamorous gowns, online speculation suggested she was channeling Jessica's style — her former rival for William's heart. This interpretation resonates strongly.
Why would Kate do this? Likely to send a clear message to Jessica Craig: the battle is over. The sapphire engagement ring subtly visible in the photo seals her victory.
Photos: Getty Images, Rex Features/FOTODOM.RU
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