Meghan Markle’s journey to becoming the Duchess of Sussex is often framed as a fairy-tale romance, but a closer look at her pre-royal life reveals a web of intriguing connections to high-profile figures, exclusive circles, and unanswered questions. From mysterious international travels to appearances at elite events, her past suggests a calculated ascent into the upper echelons of society, with ties that intersect uncomfortably with controversial figures like Prince Andrew and Jeffrey Epstein’s network.
A Questionable Encounter with Prince Andrew
One anecdote often cited is Meghan’s alleged moment of ignorance at a royal event, where she reportedly whispered to Prince Harry, “Who’s that next to your grandma?”—referring to Prince Andrew, a man whose face has graced tabloids and royal broadcasts for decades. The story paints Meghan as a naive newcomer, but skepticism abounds. Was she truly unaware of the Queen’s second son, or was this a performance to downplay prior familiarity? The question lingers, especially given the recurring overlap between Meghan’s pre-royal movements and Andrew’s social orbit.
Early Ambitions and Elite Access
Long before her royal engagement, Meghan was navigating elite circles with surprising ease. In the early 2000s, a UK journalist recalls meeting a young Meghan, then an aspiring actress fresh off a messy divorce. Over drinks, she spoke of her struggles but also name-dropped footballer Ashley Cole, known for his high-profile lifestyle. The journalist noted her demeanor shifted when she realized he was well-connected—she wasn’t there to charm but to secure press attention. This encounter hints at Meghan’s early knack for leveraging relationships for visibility.
Her college years add more intrigue. While Meghan claimed a semester abroad in Argentina, records suggest she also spent time in Spain with no clear academic ties. Friends from her Northwestern University sorority recall her boasting of yachting in the Mediterranean and traveling to Thailand with “wealthy men” in 2001. One name that surfaces is Juan Elias, a low-profile billionaire with close ties to Prince Andrew. Elias was known to frequent Meghan’s sorority events in the U.S. and joined Andrew on trips to Thailand during the same period Meghan referenced. These connections raise questions: how did a college student gain access to such exclusive circles?
Patterns of Proximity
Meghan’s presence in elite spaces continued post-college. In 2012, she appeared in Hong Kong, mingling at high-profile events despite Suits being a modest TV show at the time. A now-deleted interview clip reportedly mentioned “royals” in attendance—coincidentally, Prince Andrew was in Hong Kong during the same period. No evidence confirms a direct meeting, but the pattern of Meghan and Andrew occupying the same rarefied spaces is striking.
The 2013 Novak Djokovic Foundation Gala in New York further fuels speculation. Attended by royalty, fashion moguls like Anna Wintour, and Prince Andrew alongside his daughters, the event was a magnet for the global elite. Meghan was reportedly present, yet no official photos or press mentions document her attendance. How did a then-minor actress secure an invite to such an exclusive gathering? The absence of a paper trail suggests a deliberate effort to maintain “calculated obscurity.”
Soho House and Epstein’s Shadow
Meghan’s ties to Soho House, the exclusive members-only club, provided another gateway to power. Frequented by Harry, Andrew, and other royals, Soho House was a hub for networking among the rich and ambitious. Meghan was a regular at its events in London, Istanbul, and beyond, often moving just out of the spotlight. A 2015 photo from the opening of Soho House Istanbul places her alongside actor Eddie Redmayne, yet the press failed to identify her, underscoring her ability to blend in while building connections.
More troubling are the links to Jeffrey Epstein’s circle. Meghan was photographed on a Mediterranean yacht trip with Karine Shuliak, reportedly Epstein’s last known girlfriend, and Deepak Chopra, whose name appears in leaked documents tied to Epstein’s charitable networks. These connections, alongside her presence at events like the 2017 Jamaica wedding—attended by Andrew, his daughters, and Soho House co-owner Ron Burkle, who provided Meghan a private jet—paint a picture of someone deeply embedded in a world of influence long before meeting Harry.
The Silence Speaks Volumes
What stands out most is Meghan’s silence about these episodes. She rarely discusses her travels to Spain, Thailand, or the Mediterranean, nor does she mention the elite figures who facilitated her access. Her scrubbed interviews and lack of documented presence at high-profile events suggest a carefully curated narrative. Why omit details that could have bolstered her image as a worldly, connected woman? The answer may lie in the names tied to those moments—names like Elias, Shuliak, and Andrew, whose associations carry heavy implications.
A Strategic Ascent?
Meghan’s path to royalty appears less like a chance encounter and more like a strategic maneuver through a maze of power brokers. Her ability to navigate exclusive circles, from yachts to galas, while leaving minimal traces, points to a level of sophistication beyond that of a typical aspiring actress. Prince Harry, by all accounts, was unaware of her prior proximity to his family’s orbit, particularly through his uncle Andrew’s network.
This isn’t to accuse but to question: how did Meghan Markle, a relatively unknown actress, move so seamlessly among billionaires, royals, and controversial figures? The trail of coincidences—Hong Kong, New York, Soho House, and beyond—suggests her royal romance may have been less serendipitous than it seems. As the pieces of her past remain shrouded, one thing is clear: the Duchess of Sussex’s story is far more complex than the fairy tale presented.
This article is based on public reports, social media discussions, and unverified claims circulating as of October 7, 2025. All allegations are speculative and presented under fair use for commentary purposes.
