Meghan Markle’s pre-Harry dating life laid bare by royal biographer

A new biographical account portrays Meghan Markle’s dating history long before she met Prince Harry, recounting a string of high-profile relationships and a clear focus on a path to stardom. The details, drawn from Tina Brown’s The Palace Papers and related royal biographies, center on Meghan’s life in Los Angeles, her father’s influence, and the social circle she navigated before joining the royal family.

Thomas Markle, Meghan’s father, supported his daughter’s ambitions as she grew up in California, with Brown describing a household that prioritized access to the industry’s opportunities. According to Brown, Meghan attended college with an eye toward dating within a social landscape that included “basketball hunks” and would later be described by Brown as Meghan having “her pick” of potential partners. Brown quotes Thomas Markle recounting a moment from Meghan’s college years in which she reportedly pointed to a boy and said that he would be her boyfriend, an assertion that Brown ties to Meghan’s early confidence in forming romantic connections. The timeline catalogues a succession of relationships that predate Harry, including a first boyfriend identified as Steve Lepore, a Northwestern University basketball player who dated Meghan for about five months before transferring to a North Carolina college.

Meghan’s early dating life continued with several actors and creatives. Shaun Zaken, described by Brown as a fellow actor Meghan met while studying, dated for roughly six months in 2003. She later dated Brett Ryland for about five months; Ryland would go on to work as a writer on television. Before meeting Harry, Meghan was linked to American film producer Trevor Engelson. Brown portrays their relationship as a “tender dynamic” that culminated in marriage in August 2011, followed by a separation in 2013 and a divorce in 2014. Brown notes that a wedding guest recalled Meghan sending a note requesting no social media, a request that seemed incongruous given her rising visibility from Suits and other projects. The couple’s split is described in Brown’s account as stemming from irreconcilable differences, with Engelson reportedly feeling used as Meghan’s star ascended in the industry.

Meghan’s post-Engelson dating history continued with Canadian chef Cory Vitiello, whom she reportedly dated for about two years after her divorce, with their relationship ending in 2016. Vitiello has publicly supported Meghan’s privacy, saying there is no bitterness about how their story has unfolded and emphasizing respect for Meghan’s private life even as she remains in the public eye. The arc of Meghan’s relationships ultimately intersects with the broader public narrative about how she and Harry navigated their romance in a media-saturated era.

Beyond the specifics of Meghan’s dating timeline, the accounts touch on questions about how much she researched or learned about the Royal Family before meeting Harry. In Oprah Winfrey’s 2021 interview, Meghan said she did not research what meeting the prince would entail, and Harry echoed a similar sentiment in his 2023 memoir Spare, noting that Meghan “definitely hadn’t googled us” before their first encounter. Biographers Carolyn Durand and Omid Scobie, however, in Finding Freedom, suggested that both Meghan and Harry likely did their homework on one another before their first blind date at Dean Street Townhouse in 2016, a claim that has been echoed by observers who note Meghan’s careful online curation of her public image.

Some observers and friends have offered nuanced takes on Meghan’s pre-royal life. Vanity Fair columnist Tom Fitzgerald described Meghan as someone who would likely review a restaurant menu online, a character detail that supporters say aligns with a cautious approach to opportunities and public appearances. Ninaki Prat, a friend from Meghan’s childhood, recalled Meghan’s fascination with the Royal Family—citing Diana: Her True Story on Meghan’s bookshelf and noting Meghan’s affinity for films about commoners becoming royalty, such as The Princess Diaries.

The narrative about Meghan’s dating life sits within a broader arc of how she built and managed her public persona after stepping back from royal duties. Since leaving the royal framework, Meghan and Harry have pursued a wide-ranging slate of projects, including docuseries, a book, podcasts, and other ventures, and they extended their deal with Netflix, signaling continued activity in the entertainment sphere. Settling into life at their Montecito home with Harry, Meghan has increasingly positioned herself as a media creator and CEO of her own brand, a status that Brown’s pages and other biographers trace through a long arc from Los Angeles roots to global prominence. The portrait presented in these sources is one of intentional visibility and strategic collaboration rather than a single, linear ascent.

The reporting in Brown’s The Palace Papers is supplemented by contemporaneous accounts from other outlets and biographers, including Andrew Morton’s early portraits of Meghan’s dating history and the more recent reflections in Finding Freedom. Together, they sketch a complex tapestry of a young woman who balanced ambition with personal relationships, all within a media landscape that would eventually magnify every strand of her life—from college-era dating to a televised romance that would culminate in a different kind of fairytale.

As Meghan and Harry continue to shape their public narratives through new projects and partnerships, the look back at Meghan’s pre-Harry dating life offers a window into the evolving story of how a Los Angeles girl with royal dreams became a global entertainment phenomenon. The details, while contested in parts, reinforce the notion that Meghan’s path to destiny was not a single, unbroken line but a mosaic of early relationships, professional ambitions, and carefully managed public visibility that foreshadowed the complex public life she would lead in the years to come.