Prince Andrew, the Queen’s second son and once second in line to the throne, has long been surrounded by controversy—not just because of his public roles but due to a string of scandalous personal behaviors.
From his reputation as a womanizer to his alleged bullying of staff, his story is one tangled with privilege, excess, and deep flaws.
The ‘Randy Andy’ Nickname and His Notorious Love Life
Back in his school days at Gordonstoun, Andrew earned the nickname “Randy Andy.”
It wasn’t just a playground tease — it reflected his early and well-known reputation as a confident, attractive young man who was already quite experienced with women.
This reputation only grew when he became a war hero and a heartthrob to many.
Over the years, Andrew reportedly slept with hundreds, if not over a thousand women, spanning from models and actresses to athletes and politicians.
Investigative journalist Ian Halperin even suggested the list includes porn stars and bartenders.
A friend described sex as Andrew’s “big thing,” especially since his royal duties took him all over the world, granting him plenty of opportunities.
Wild Stories from Around the Globe
His exploits have reached far and wide.
During a 2006 trip to Thailand for the King of Thailand’s diamond jubilee, it was reported that over 40 women visited Andrew’s hotel room, with new arrivals constantly replacing those who left.
Hotel staff, used to such scenes, were reportedly shocked by the sheer number.
One model, recalling her experience in the late 1980s, described Andrew’s boundary-pushing behavior and open marriage arrangement.
After a brief whirlwind romance that included trips to exotic islands, she felt used and discarded.
A Pattern of Objectification and Exploitation
Andrew’s behavior wasn’t limited to fleeting flings.
Those who worked closely with him often witnessed a pattern of objectifying women and even mistreating staff.
A masseuse at his home said his massage requests were uncomfortable, with Andrew insisting on being naked and making inappropriate sexual comments throughout.
Staff who worked at Buckingham Palace described him as rude and demanding, with little respect for those around him.
Stories of him bringing “the worst bunch of tarts” to dine with the Queen Mother and pressuring staff into uncomfortable situations circulated widely.
His arrogance and lack of empathy were obvious even to those who were supposed to serve him.
Social Faux Pas and Crude Behavior
Despite his status, Andrew’s social skills were often described as awkward at best and outright boorish at worst.
He was known for crude jokes, juvenile pranks like throwing tent flysheets into rivers, and humiliating guests at parties.
A favorite pastime reportedly involved tricking guests into slapping open tubes of mustard into their faces.
At formal dinners, his tasteless humor and need for attention grated on everyone present.
Friends and acquaintances alike found him difficult to tolerate, noting his inability to engage in meaningful conversation beyond talking about himself.
Struggles with Identity and Loneliness
Despite the bravado, many who knew Andrew say he struggled with loneliness and identity.
Navigating the balance between his royal duties and personal life seemed to confuse him.
Friends described a man who was awkward in social settings, often shielding himself behind his royal status.
Even in moments of vulnerability, Andrew showed signs of insecurity.
His reactions ranged from childish stubbornness to cruelty when feeling ignored or disrespected.
Bullying Allegations and Tensions Within the Royal Family
Andrew’s difficult personality reportedly extended to bullying staff.
In 2021, as Meghan Markle faced accusations of bullying, there were whispers that Andrew’s own treatment of aides was even worse.
Some staff were moved or reduced to tears because of his unreasonable demands and profane outbursts.
His relationships with his nephews, especially Harry, were strained.
A 2013 family confrontation reportedly ended with Harry landing a punch on Andrew, leaving him with a bloody nose.
Andrew’s dismissive and cruel comments about Meghan Markle and Harry’s decisions only worsened family tensions.
A Royal Living by His Own Rules
Throughout his life, Andrew seemed to believe the rules simply didn’t apply to him.
From petty theft in school to ignoring traffic laws and security protocols, he repeatedly flaunted boundaries with little consequence.
His careless driving, rude treatment of police and staff, and brazen disregard for property rules exemplify a sense of entitlement bred by decades of privilege.
The Family’s Attempts to Manage the Fallout
By 2021, the Royal Family agreed that Andrew’s continued presence was damaging the monarchy’s reputation.
His ungracious attitude and public scandals made him a liability.
Tensions with his family grew, particularly with William, who reportedly sought to evict Andrew and his ex-wife Sarah from their Windsor residence.
The internal royal dynamics are strained, reflecting deep fractures caused by Andrew’s behavior and the controversies surrounding him.
The Book They Didn’t Want You to Read
Much of this story comes from a new book, Entitled: The Rise and Fall of the House of York by Andrew Lownie, which offers an unvarnished look at Andrew’s life and character.
The York family reportedly tried to block its publication, refusing to cooperate or allow others to speak.
Despite attempts to suppress the narrative, the book draws on interviews with hundreds of sources, painting a detailed picture of how Andrew’s flaws and the royal institution’s failures intersected to create this dramatic downfall.