Awkward Sarah Ferguson Moments That Were Captured By Millions

Sarah Ferguson's history with the British royal family spans far back to her early childhood. From becoming friends with the late Princess Diana, Ferguson — also known as Fergie — ushered her way into royalty simply by association. That was until 1985 when she reconnected with her husband-to-be, Prince Andrew. After what was presumed to be a compelling encounter, the two married in 1986, resulting in a six-year marriage. 

Although Ferguson and Andrew built a strong family home — introducing daughters Princess Beatrice and Princess Eugenie in the process — numerous rumors of infidelity alongside her issues with Andrew's hectic traveling schedule led to their relationship's demise. While it's never fun to go through personal disputes publicly, this would be the first of what seemed to be a never-ending cycle for the Duchess of York.

As a well-known philanthropist/author, she built herself a career that is quite commendable. Ferguson, however, also built a reputation for being caught in embarrassing scandals. Whether it be the well-known sting operation where she offered access to her ex-husband in exchange for money, or her public disputes with the royal family, Ferguson has racked up several shameful moments many of us would want to be deleted from the internet. During one interview with The Telegraph, Ferguson appeared to have made peace with her past mistakes: "I am proud of my failings." We revisit all the awkward moments Sarah Ferguson has found herself in.

What appeared to be a happy marriage soon became a well-documented chain of unfortunate events that led to Sarah Ferguson and Prince Andrew's separation. The hardships Andrew's naval career created for the pair slowly became unbearable to manage. With the two at their wit's end, they eventually announced their split in March 1992 — officially divorcing in 1996 — after rumors of infidelity began to spread.

Following their breakup, Ferguson found herself in hot water as explicit photographs of her and financial adviser John Bryan reached the press. Spotted in France, Bryan was seen by the poolside sucking on the toes of the duchess. Attempting to cover their tracks, royal expert Richard Kay reported to The Daily Mail, stating, "Bryan promised her everything would be fine, but I could see in his face that he didn't really believe it" (via The Mirror).

Given the royal family's reputation, the "toe-sucking" scandal got her in trouble with her in-laws. With even Princess Diana left to hope for the best for her redheaded friend, Ferguson faced a slew of tabloids alongside criticism from her family for years to come. While her ex-lover went on to claim the photograph seemed more incriminating than it actually was, per The Daily Mail, the shame it brought Ferguson was mortifying. Unfortunately, this would be the first instance of her more shameful moments reaching the press.

Alongside the continuous publications attacking her character, Sarah Ferguson faced financial problems after her divorce from Andrew. With the duchess allegedly owing £600,000 after her lifestyle business, Hartmoor, fell apart, Ferguson was desperate for money. As a result, the duchess tried to pay off her debt any way she could, even if it meant accepting cash from convicted sex offender Jeffrey Epstein. 

Sadly, this wouldn't be the lowest Ferguson went for quick cash. In 2010, a sting operation constructed by News of the World caught Ferguson on camera agreeing to trade access to her ex-husband, Prince Andrew, in exchange for £500,000 (via The Guardian). The duchess told reporter Mazher Mahmood, "Look after me, and he'll look after you ... you'll get it back tenfold."

Though her reputation wasn't entirely positive, the scandal severely damaged the ounce of respect those in the royal family had for her. After releasing an apologetic statement regarding her actions, Ferguson appeared alongside Oprah Winfrey to further explain the details of that night. In addition to revealing that she's never watched the video, the duchess claimed her inebriated state of mind was the catalyst for her behavior (via YouTube). "I haven't faced the devil in the face because I was in the gutter at that moment," she told Oprah. "I'm very aware of the fact that I'd been drinking, you know, that I was not in my right place."

Sarah Ferguson and Princess Diana's relationship started before their affiliation with the royal family. As fourth cousins, the two were childhood friends who eventually reconnected during the later parts of their lives. Though Ferguson was Diana's main confidant, Diana had a hand in drawing Ferguson into the royal family. From reintroducing her to Prince Andrew to inviting her to Buckingham Palace on several occasions, Ferguson became well-known among the royal family thanks to Diana. Given their kinship, the duchess recalled a mischievous venture the two went on following her engagement to Andrew. 

During a recent appearance on "The Kelly Clarkson Show," the Duchess of York revealed that her bachelorette party — or hen party — ended with the soon-to-be royal-in-laws in the back of a police van (via YouTube). The two allegedly went to a nightclub decked out in police attire. Shortly after their arrival, the servers believed the two were actual police officers and kicked them out, stating, "Excuse me, this is a members' club. And it's for fun, and we don't serve police officers here."

The pair then left the club only to be met with handcuffs, a police van, and a bag of "smoky bacon-flavored crisps." According to Ferguson, the two were arrested simply for impersonating police officers. Given her royal status, Ferguson stated that it didn't take long for the police officers to realize they had arrested Princess Diana.

Though her shortcomings would be the focal point of numerous publications, Sarah Ferguson has contributed to a fair share of charity organizations intended to help those in need. Whether it be supporting the Teenage Cancer Trust charity or founding the Children in Crisis foundation, the Duchess of York has been known to be a philanthropist throughout her time in the limelight. Despite her honest intentions, these philanthropic ventures took a turn for the worst amid her 2009 documentary covering Northern Moor, Wythenshawe.

Ferguson collaborated with ITV to produce "The Duchess on the Estate" (via YouTube). The documentary sought to capture the realities of the impoverished area in Manchester and encourage those in the area to make positive changes. However, the portrayal displayed only angered the residents who lived in the area. In the wake of its premiere, a local news channel broadcast the residents' reaction to the negative publicity Ferguson allegedly gave to their community as they organized a protest at Wythenshawe Park.

With claims of the Duchess of York calling Northern Moor "broken Britain," Ferguson faced massive backlash for her philanthropic attempt. Ferguson went on BBC Radio Manchester to clarify comments made in the documentary. "From the very beginning of this, I have never described the area as 'broken Britain,'" she said (via YouTube). "And I always told the production company that I will never ever want it to be called 'broken Britain' because I don't believe it is."

There's no doubt that several publications saw Sarah Ferguson as a punching bag for articles revolving around the royal family. Ever since her toe-sucking scandal, the Duchess of York faced the wrath of her in-laws and the public, even when their opinions were unwarranted. Aside from clarifying her actions, Ferguson has taken accountability for her mistakes in the past. The same can be said for the unfortunate bribery scandal, which saw the redheaded royal sit with Oprah to express her deep regrets.

As a prolific writer, Ferguson also used illustration to explain her misinterpreted behavior. However, the openness displayed in her written work didn't stop interviewers from probing questions regarding her numerous scandals. In an awkward 2013 interview from "60 Minutes Australia," Ferguson appeared tired of intrusive questions about the well-documented sting operation.

After declaring she returned the money given to her, she warned the interviewer, stating, "Don't try and trick me now because I'm not going to play this game" (via YouTube). Ferguson's discomfort became apparent as he continued to disregard her boundaries, by which Ferguson punctually stated, "What more can I say?" As he tried to continue the interview, Ferguson glanced over at her team and promptly walked out for a five-minute break. Although she finished the interview afterward, her rejuvenated attitude didn't dispel the awkward air in the room from their tense back-and-forth.

Given the numerous scandals Sarah Ferguson has found herself in, we can assume that the higher-ups in the royal family saw the redheaded duchess as an embarrassment. As a result of her divorce from Prince Andrew, her title of royal highness was stripped from her — which seemingly caused the royal family to cease any relation they had to Ferguson. Though she made public apologies after each mishap, there were times when the royal family excluded her from specific events, like her nephew's wedding.

On April 29, 2011, Prince William and Princess Catherine got married at Westminster Abbey. With everyone from the royal family receiving an invite to the event, Ferguson was disappointed to learn that she wasn't included. As awkward as it may have seemed, it only became more awkward when she learned that Prince Andrew and her daughters, Princess Beatrice and Princess Eugenie, were attending the wedding as well. Ferguson saw this as an opportunity to travel to Thailand so that she could "try and heal" (via Town & Country). However, the disappointment was felt publicly during her interview with Oprah Winfrey in May of the same year. When asked about the pain she felt for not being invited, she responded, "It was so difficult because I wanted to be there with my girls and to be getting them dressed and to go as a family" (via YouTube).

Personal conversations regarding mental health are likely kept within the confines of the parties involved. In Sarah Ferguson's case, her journey to self-discovery was captured by millions, thanks to the help of Dr. Phil and Oprah, who teamed up for an OWN Network special titled "Finding Sarah" in 2011 (via YouTube). Among the several revelations Ferguson made throughout her illustrative work and interviews, none of them was as awkward an encounter as she had with Dr. Phil to find the root cause of her mental issues.

While discussing the details of the infamous bribery scandal, Ferguson claimed she has self-sabotaging tendencies. Though Dr. Phil never disagreed, he questioned why this was the case. He then suggested that Ferguson wasn't being honest about the cause of her mental issues, to which she replied, "You're the genius here. I'm asking for your help. So you tell me what you think, and I'll answer it because it'll really help me."

As she continued to reiterate that she was not in denial, Dr. Phil insisted that she knew more than she let on. After their uncomfortable exchange, the two eventually made a breakthrough and determined that the source of Ferguson's self-sabotaging behaviors was her need for approval. What Dr. Phil considered an addiction gave Ferguson the closure she needed. "Well, it's really exciting in a way that I'm an addict, because at least we can label it," she told Dr. Phil.

Prince Andrew's connection to Jeffrey Epstein came to haunt him in 2015 as Virginia Giuffre accused the prince of sexual abuse. Though the royal family isn't new to rumors seeing the light of day, this wasn't necessarily a headline that could be swept under the rug. Queen Elizabeth II stripped Prince Andrew of his military affiliations and royal obligations until the matter was resolved. In 2021, Giuffre filed a lawsuit against Prince Andrew, and by 2022, Prince Andrew settled in court for an undisclosed amount after failing to convince the judge to dismiss the suit.

While the case would later be handled within the confines of the courtroom, Sarah Ferguson publicly defended her ex-husband amid the accusations. In one instance, her opinion of the entire situation appeared distasteful. During her appearance on "The Meredith Vieira Show" in 2015, the Duchess of York revealed that she was enraged when she first heard about the allegations. In defense of Prince Andrew, Ferguson stated that Giuffre made up "salacious lies" and declared that her family "will not be defeated" (via YouTube). Although the gesture was made with pure intentions, Ferguson seemed to disregard the severity of the alleged crimes and claimed it was an attack on her family.

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).

Though Sarah Ferguson never held a grudge against Prince William for not inviting her to his wedding, she got to watch her daughter, Princess Eugenie, tie the knot with long-time boyfriend, Jack Brooksbank, in 2018. The sheer excitement alone from learning about their engagement was enough to get her caught up in yet another awkward moment which saw her release a slew of pictures on social media declaring her fondness for the two. Although her barrage of motherly love was allegedly silenced by the royal family — disrupting a string of future appearances she was scheduled to attend — this wasn't enough to keep her from Eugenie's special day as she got to attend the spectacle alongside several notable guests such as Cara Delevingne, Naomi Campbell, and Kate Moss.

Among the numerous memorable moments captured at the wedding — such as Prince George and Princess Charlotte's bridal performance or Princess Beatrice reading an excerpt from F. Scott Fitzgerald's "The Great Gatsby" — one of which saw Robbie Williams' daughter, Theodora Williams, have a hilarious yet embarrassing exchange with the Duchess of York as they were making their way down the steps of the chapel (via YouTube).

In a video capturing the moment, you could hear Theodora ask Ferguson if she was the queen, to which she responded, "No." Theodora would then ask Ferguson, "Are you a princess?" which prompted Ferguson to say, "Yes."

Sarah Ferguson has found herself on the receiving end of harsh criticism regarding her fashion choices. The strict limitations to what members of the royal family are supposed to wear don't allow for much variety. Though Ferguson liked to push the boundaries of what was considered appropriate for classy events, outfits worn by the Duchess of York weren't as risqué as one may assume. Despite this, Ferguson — like many other celebrities — has had her fair share of wardrobe malfunctions that were out of her control.

One instance occurred in 2008 while she attended a polo game with her family (via The Daily Mail). As Ferguson — who was decked out in a knee-length dress paired with a white jacket — made her way across the field, the wind blew her skirt up, accidentally exposing a little too much of her to those in attendance. Another instance occurred in 2017 while she was walking to a charity party dedicated to The Andrea Bocelli Foundation and the Muhammad Ali Parkinson Center in Rome (via The Daily Mail). Although Ferguson was pictured alongside notable celebrities such as Susan Sarandon and Tiziana Rocca, this was after she was photographed with the hem of her black dress caught on her sleeve. Unbeknown to her, she raised her hand high enough for the front of the dress to expose her. In perfect timing, the paparazzi captured the awkward moment, and publications began to plaster the photograph all over the internet.