Prince Andrew stripped of royal titles: A look at his lovers, flings, scandals, and past relationships

The gates of Royal Lodge, once a symbol of quiet privilege within Windsor Great Park, have now become a metaphor for Prince Andrew’s final exile from royal grace. Following reports of his impending eviction from the sprawling estate, the home he has shared for decades with his former wife, Sarah Ferguson, the Duke of York’s life has again returned to public scrutiny.

Stripped of his royal titles, patronages, and military honours in the wake of the Jeffrey Epstein scandal, Andrew has been rendered an anachronism within the very institution that once defined him. This latest turn is not just about property or privilege; it marks the steady unravelling of a man once celebrated as the dashing “action prince” of the 1980s, a naval officer and war hero, whose romantic exploits filled the gossip columns long before his reputation turned to ruin.

His removal from Royal Lodge, reportedly at the King’s insistence, symbolises both a practical and moral repositioning of the monarchy, a quiet but decisive act of distance. It also invites a retrospective gaze. For decades, Prince Andrew’s personal life mirrored the glamour and turbulence of the circles he inhabited, a procession of models, actresses, socialites and heiresses whose names once lit the pages of Tatler and Hello! with a distinctly aristocratic sparkle.

Before scandal consumed his name, he was Britain’s most eligible bachelor, his romantic life tracked with the same fascination once reserved for film stars and footballers.Now, as his public standing collapses beneath the weight of past associations, it feels timely, perhaps inevitable, to revisit the women who once defined Prince Andrew’s personal mythology. From early teenage romances to headline-making affairs and royal marriages, their stories together form a revealing social map of a man whose private pursuits have always shadowed his public downfall.

The women: A chronology of Prince Andrew’s romantic history

1. Sandi Jones (1976) Prince Andrew met Canadian teenager Sandi Jones during his exchange programme at Lakefield College School in Ontario in 1976, when he was 16. They became close while he stayed in Canada and reconnected during the 1976 Montreal Olympics, where Andrew attended to support his sister, Princess Anne. Their teenage romance was described as sincere but ultimately brief, curtailed by royal expectations and geography.

According to author Nigel Cawthorne, Andrew once asked her to marry him and elope to Gretna Green, though both knew it was unrealistic. The two remained on amicable terms, and Jones later attended Andrew’s wedding to Sarah Ferguson in 1986. She later confirmed they were “very, very close” and shared deep affection, though their relationship ended naturally as his royal duties increased.

2. Catherine Oxenberg (circa 1980–1981)

Prince Andrew’s early 1980s romance with American actress Catherine Oxenberg was brief but notable. Oxenberg, best known for her later role in the television series Dynasty, reportedly received a marriage proposal from Andrew when she was just 18.

The two met through royal and social circles, and their relationship reflected mutual youthful attraction and royal compatibility, as Oxenberg herself descends from Serbian royalty. She ultimately declined the proposal to pursue her acting career in Hollywood. Their association ended amicably, with both moving on without public acrimony.

Oxenberg would later become known for her work as an actress and advocate, particularly for her efforts to rescue her daughter from the NXIVM cult.

3. Carolyn Seaward (Early 1980s)

Carolyn Seaward, crowned Miss United Kingdom in 1979 and a Miss Universe finalist, dated Prince Andrew briefly in the early 1980s. Their relationship occurred during his bachelor years and was widely covered by the press, which often linked Andrew to models and actresses of the period. The pair met through social events connected to London’s fashion and aristocratic circles. The relationship was short-lived and ended quietly, with no controversy or official acknowledgment from Buckingham Palace.

Seaward continued her modelling and acting pursuits, and her name remains among the first in Andrew’s list of pre-marital romantic links.

4. Koo Stark (1981–1983)

American actress and photographer Koo Stark met Prince Andrew at a party celebrating his 21st birthday in 1981. The pair dated for approximately two years, during which Stark was introduced to the royal family and spent time at Balmoral and Buckingham Palace. Their relationship was serious, and Andrew was reportedly deeply attached to her.

However, media attention intensified after tabloids publicised Stark’s past acting roles, including a topless scene in an art-house film, which led to royal disapproval.

Under family pressure, Andrew ended the relationship in 1983. Decades later, Stark publicly defended Andrew amid his controversies, describing him as a “good man” and recounting the kindness he showed during their time together.

5. Brooke Shields (1984)

In 1984, Prince Andrew was briefly linked to American actress and model Brooke Shields.

Reports at the time suggested that the two met during social gatherings in New York and shared a short-lived friendship that was interpreted as romantic by the press. Shields, then a rising Hollywood star, was one of several celebrities connected to the young prince during his naval career and regular transatlantic visits. Their connection was brief, informal, and ended without public remark or confirmation from either party.

6. Vicki Hodge (1984–1985)

British model and actress Vicki Hodge dated Prince Andrew during the mid-1980s, following his split from Koo Stark. The pair were frequently seen together at society events and nightclubs, marking Andrew’s growing reputation as a “party prince.” Hodge, known for her roles in Confessions of a Sex Maniac (1974) and her modelling career, was also associated with London’s social elite. Their relationship reportedly faced royal disapproval due to Hodge’s previous long-term relationship with actor and gangster associate John Bindon.

The romance ended around 1985, as Andrew’s royal obligations intensified and scrutiny around his personal life increased.

7. Sarah Ferguson (1986–1996)

Prince Andrew married Sarah Ferguson on 23 July 1986 at Westminster Abbey, after being introduced by Princess Diana. Upon marriage, he became the Duke of York, and the couple had two daughters, Princess Beatrice (born 1988) and Princess Eugenie (born 1990). Their marriage was initially affectionate but strained by Andrew’s naval commitments and tabloid scrutiny.

They separated in 1992 and formally divorced in 1996.

Despite the split, they continued to live together at Royal Lodge in Windsor from 2008 until 2025, maintaining a close friendship and co-parenting partnership. Ferguson, who retained her title as Duchess of York, was later linked to Jeffrey Epstein, from whom she accepted financial assistance to clear debts.In the wake of renewed royal pressure and reports that Prince Andrew is to be stripped of his remaining royal privileges and evicted from Royal Lodge, the Duchess of York is also expected to move out. As People reported, Sarah has begun exploring alternative accommodation options since the former prince will likewise be required to vacate the royal premises.

Their long cohabitation at the Windsor estate now appears to be nearing its end amid mounting controversy over Andrew’s standing within the monarchy.

8. Christina Estrada (Early 1990s)

American supermodel Christina Estrada was romantically linked to Prince Andrew in the early 1990s. The pair were seen together at various social gatherings in London and abroad. Estrada, who appeared in the Pirelli calendar, was a regular on the international modelling circuit at the time.

Their relationship was never formally confirmed by Buckingham Palace, and details remain limited, though it was viewed as one of Andrew’s post-marital associations before his marriage. Estrada later married Saudi billionaire Walid Juffali in 2001, with whom she had a daughter. The connection with Andrew ended amicably and remained a brief chapter in his dating history.

9. Lady Victoria Hervey (1999)

Lady Victoria Hervey, British socialite and daughter of Victor Hervey, 6th Marquess of Bristol, dated Prince Andrew around 1999.

Their relationship was brief, lasting several months, but it placed her firmly within his circle of aristocratic companions. Hervey, known for her fashion and media career, lived briefly in Epstein’s London apartment during that era but later clarified that her association with Epstein was unrelated to Andrew.

Years later, she became one of Andrew’s public defenders amid his controversies, describing media portrayals of him as unfair.

Their romance ended amicably before the turn of the millennium.

10. Caprice Bourret (2000)

In 2000, American model and media personality Caprice Bourret was briefly linked to Prince Andrew. They met at a private dinner party in the English countryside and were seen together for about two months. Andrew invited her to Buckingham Palace for dinner and, in an unusual move, reportedly allowed her to sit on the Queen’s throne. Caprice also introduced Andrew to her masseuse, Denise Martell, who later became one of his companions.

The relationship ended after Caprice decided she was not romantically interested in him and felt uncomfortable with media speculation. Their association was short-lived and amicable.

11. Denise Martell (2000)

Playboy model and actress Denise Martell met Prince Andrew at Heidi Klum’s Halloween party in New York in 2000. According to accounts in Andrew Lownie’s Entitled: The Rise and Fall of the House of York, the two quickly became close, and Andrew gave her his phone number the same night.

They reportedly shared a brief affair lasting around 72 hours during Andrew’s trip to New York. Martell later recounted that Andrew fed her chocolate-covered strawberries during their first meeting. There was no long-term relationship, and Martell has never been linked to Jeffrey Epstein or commented publicly on Andrew’s later controversies.

12. Caroline Stanbury (2000–2001)

British socialite and reality television personality Caroline Stanbury dated Prince Andrew around 2000–2001, shortly after his divorce.

The pair were seen together at high-profile events, including a gala in Martha’s Vineyard hosted by Bill and Hillary Clinton. Their relationship drew media interest due to their age gap and Stanbury’s rising celebrity status. Reports suggested that Sarah Ferguson disapproved of the relationship.

The romance ended within a year under media pressure. Stanbury later became a star on Ladies of London and The Real Housewives of Dubai.

13. Erica Baxter (2001)

In 2001, Prince Andrew was photographed with Australian singer and model Erica Baxter, later known as Erica Packer, during a holiday in Thailand. Paparazzi captured the pair together on a beach, with the images sparking speculation of a brief romance. Baxter, an emerging performer in the Australian entertainment industry, was later married to businessman James Packer. The encounter with Andrew was described as casual and short-lived, ending without public comment.

It occurred during Andrew’s early 2000s period of short-term flings following his divorce from Sarah Ferguson.

14. Virginia Roberts Giuffre (2001, Allegations)

Virginia Roberts Giuffre accused Prince Andrew of sexual abuse in 2001, alleging she was trafficked by Jeffrey Epstein and Ghislaine Maxwell at age 17. She claimed to have been forced into sexual encounters with Andrew in London, New York, and on Epstein’s island. A widely circulated photograph showed Andrew with Giuffre and Maxwell in Maxwell’s London home.

Andrew denied all allegations. In 2022, he reached an out-of-court settlement, paying an undisclosed sum to Giuffre’s charity for survivors of sex trafficking.

Giuffre later published a memoir, Nobody’s Girl (2025), released posthumously after her death by suicide earlier that year.

15. Angie Everhart (Early 2000s)

American model and actress Angie Everhart met Prince Andrew through her former father-in-law, actor George Hamilton, who arranged a dinner between them.

Everhart recalled that Hamilton told her Andrew “likes redheads.” The two went on a date in Los Angeles, but the relationship never progressed further. Their meeting occurred in the early 2000s, around the same period Andrew was linked to several models. The connection remained casual, and there were no further sightings or reports after their dinner.

Spanish-Filipino model and PR professional Alexandra Escat was linked to Prince Andrew in the summer of 2010 after being photographed with him on the yacht Yalla off Sardinia. The pair were pictured in relaxed poses, including Escat applying sunscreen to Andrew’s back.

Their friendly behaviour led to speculation of romance, though both denied any romantic involvement. Escat stated they were simply part of a larger social group and maintained they were only friends. She later hired a publicist to manage the sudden media attention. The episode ended shortly after the photographs circulated.

17. Monika Jakisic (2014)

Croatian-born model Monika Jakisic, a former girlfriend of actor George Clooney, was romantically linked to Prince Andrew for about five months in 2014.

They were seen dining at the Royal Thames Yacht Club and celebrating Andrew’s birthday in London. Media dubbed her the “Croatian Sensation.” Engagement rumours surfaced after Jakisic posted a photo of a diamond ring, which Andrew’s representatives quickly denied.

The pair’s relationship ended quietly and amicably later that year, with both moving on to other relationships. Jakisic maintained a low profile afterward.

18. Dara Tomanovich (2014)

Canadian model and actress Dara Tomanovich briefly dated Prince Andrew in 2014. They were spotted together at the Royal Ascot races and several social events during that summer. Tomanovich, known for her modelling and television appearances, represented another of Andrew’s high-society relationships during the 2010s. Their relationship was discreet and short-lived, fading from public attention after a few months.

Neither commented publicly on the relationship.

19. Kylie Minogue (2017–2018)

Australian singer and actress Kylie Minogue was rumoured to have dated Prince Andrew briefly between 2017 and early 2018, following her breakup with actor Joshua Sasse. The two reportedly reconnected through royal circles and mutual friends after having known each other for years. Media outlets claimed they became “quietly inseparable” for a short period, though neither confirmed the relationship publicly.

The romance was largely speculative and is believed to have ended quietly. Minogue and Andrew have remained cordial through shared social circles.

The 'Playboy Prince' and the unravelling

In the years following his naval service during the Falklands War, Prince Andrew emerged as a central figure in Britain’s royal theatre — young, handsome, and conspicuously sociable. Tabloids dubbed him “Randy Andy,” a moniker that, for a time, was worn like a badge of charm. He moved through London’s nightlife and international society with the ease of a man born to entitlement but restless in its confines. His associations with models, actresses and aristocrats became regular fixtures in the gossip press, a pattern that began as youthful indulgence and later hardened into reputation. By the early 2000s, the prince’s social orbit had grown increasingly eclectic, extending beyond the predictable upper circles of British high society.

His friendships began to attract scrutiny, none more damaging than his association with Jeffrey Epstein, the disgraced American financier whose name would eventually tether Andrew’s to scandal. The prince’s once-celebrated charisma began to read as carelessness, his relationships no longer charming but questionable. His image as a bachelor prince, once glossy, buoyant and effortlessly privileged, darkened into that of a man adrift, out of touch with consequence.

In many ways, Andrew’s downfall was a slow unspooling rather than a sudden collapse. The same social appetite that had once made him magnetic proved, in the end, his undoing. When his connection to Epstein became a matter of public outrage, his romantic past, once dismissed as the harmless dalliances of a royal spare, was revisited with sharper eyes. It revealed a lifetime of indulgence, punctuated by brief sincerity but seldom by discretion.What follows is not a moral inventory but a record, a clear, chronological account of the women who crossed paths, and sometimes hearts, with Prince Andrew. From teenage flirtations and earnest proposals to fleeting affairs and public marriages, these relationships sketch the private history behind the public façade of a man who never quite outgrew the myth of the playboy prince.