Recent revelations from the latest tranche of Epstein files have cast new light on Sarah Ferguson's persistent pursuit of wealthy partners following her divorce from Andrew Mountbatten-Windsor. Emails from January 2010 show Sarah, then 67, proposing marriage to Jeffrey Epstein, even after his conviction for soliciting sex from underage girls. In one email, she told the billionaire paedophile financier, "You are a legend. I really don't have the words to describe my love, gratitude for your generosity and kindness. Xx I am at your service. Just marry me." This was not her first proposal to Epstein; in September 2009, she had suggested he marry an unnamed woman with a 'great body' before adding, 'Ok, well marry me and then we will employ her.' These exchanges underscore a pattern in the former Duchess of York's life, driven by her 'Duchess of Excess' reputation and millions in debt incurred while maintaining a lavish lifestyle.

Ferguson's romantic history reveals a consistent preference for wealthy and influential men. Her first serious boyfriend was Paddy McNally, a motorsports executive worth over £600 million, whom she eventually left for Andrew. After separating from Andrew in 1992, her relationships continued to be marked by a search for financial security or a significant figure.

American oil tycoon Steve Wyatt entered her life after they met at the Houston Grand Opera’s British Opera Festival in 1989. Cracks were already appearing in her marriage, and royal author Andrew Lownie noted Sarah was 'receptive to falling in love,' upset by Andrew's alleged bullying and infidelity. 'Lonely' Sarah was 'enormously attracted' to Wyatt, son of oil magnate Oscar Wyatt. Their friendship deepened quickly, with Sarah visiting his family ranch. Despite a clairvoyant friend warning her against the relationship, Sarah's impulses prevailed. By December 1989, their affair had begun, a relationship that, according to Lownie, would 'eventually lead to her divorce.' Photos of Fergie and Wyatt on a romantic getaway in May 1990 were leaked to the press in 1992, raising serious questions about their relationship's nature and even showing her then one-year-old daughter Princess Beatrice on Wyatt's knee. Shortly after, Andrew and Fergie announced their separation in March 1992, with author David Leigh attributing Wyatt as the 'main reason for the breakdown' of their marriage. However, this whirlwind affair did not have a happy ending for Sarah. She was heartbroken to learn of Wyatt's engagement to Cate Magennis in 1993, lamenting, 'I can’t have the man I love because he’s getting married. What’s the matter with me? Why didn’t he marry me?' Her longing was so intense that she followed Wyatt and his new wife to a London restaurant, peering through the window, but was too hesitant to enter.

After Wyatt returned to the United States in early 1992, his friend, John Bryan, stepped in. Bryan invited Fergie to dinner, and they 'slept together' that night. Lownie observed that 'the duchess was playing the men in her life off against each other,' using Bryan's closeness to taunt Wyatt and demonstrate her attractiveness to her still-admiring husband. Bryan once exposed the extent of Fergie's 'excess,' detailing her £860,000 annual expenditure, including significant sums on staff, gifts, flowers, parties, travel, and clothes, with £25,000 spent in an hour at Bloomingdale's. Bryan was also central to the infamous 'toe-sucking' scandal in August 1992. Decades later, he described the moment as a 'beautiful family moment,' part of a game of Cinderella with her daughters. Bryan and Sarah's relationship reportedly continued for another four years, during which they lived together at Romenda Lodge.

Amidst her relationships, Fergie developed an intense 'schoolgirl crush' on John F. Kennedy Jr., the dashing son of the assassinated American president. Despite Kennedy being in a relationship with actress Daryl Hannah, Fergie was determined to meet him, inviting him for drinks or dinner. When Kennedy canceled, citing a prior engagement, Fergie was so concerned it was an excuse that she ordered staff to 'spy on his apartment all night.' Her obsession grew further when she learned her former sister-in-law, Princess Diana, had met Kennedy. Fergie, assigning him the code name 'Number Nine' in her imagined order of lovers, furiously stated, 'He's mine! Why can't she just leave him alone?' She pored over articles and photos of him, asking friends about their compatibility, a crush that felt 'incredibly real' despite never having met him.

By November 1997, Fergie had shifted her sights to Italian nobility, dating wealthy Tuscan aristocrat Count Gaddo della Gherardesca. Though he professed his love for Sarah, he denied marriage rumors. The two spent time skiing, socializing in London, or traveling the world, with Sarah also relaxing at the Count's home in Tuscany.

More recently, in 2015, rumors surfaced that Fergie, then 55, was 'besotted' with Spanish internet entrepreneur Manuel Fernandez, eight years her junior. Fernandez, founder of the troubled lifestyle company vVoosh, even accompanied her to Bob Geldof's wedding. Although she denied the rumors, calling him a 'good friend,' a charitable venture they worked on together, vVoosh Charitable Foundation, later faced scrutiny. In 2025, vVoosh itself folded after receiving over £1 million in taxpayer cash without launching a single product, and its sister charity was significantly overdue on reporting accounts, having spent only a small fraction of its income on charitable activities.

Despite her turbulent romantic life and financial woes, some relationships endured as friendships. Paddy McNally, her first serious boyfriend, remained a close confidant. After Virginia Giuffre sued Andrew for sex assault, McNally invited Fergie, her daughters Beatrice and Eugenie, and their husbands to his Verbier ski chalet for a lavish New Year's Eve party, even funding an expensive fireworks display. This enduring friendship highlights a constant in Sarah Ferguson's life: a reliance on influential and wealthy figures, whether as romantic partners or steadfast supporters, to navigate her complex public and private life.