Meghan Markle’s pre-Harry dating life laid bare by royal biographers and friends

A new profile of Meghan Markle’s life before she met Prince Harry compiles details from royal biographer Tina Brown’s The Palace Papers, with additional context from close friends and biographers. The material portrays a young Meghan growing up in Los Angeles with clear career ambitions, supported by her father, Thomas Markle, a television lighting director who helped finance the best experiences and occasionally accompanied her to industry events when he was nominated for an Emmy. Brown reports that, in college, Meghan had her pick among peers considered desirable, and that her father recalled Meghan as someone who knew what she wanted. The narrative emphasizes Meghan’s early awareness of her appeal to men, a theme that would be echoed by those who knew her in the industry long before she joined the royal family.

Her earliest publicly known relationships began in college and soon moved into a string of short romances that preceded her connection with Harry. The first boyfriend widely cited is Steve Lepore, a basketball player she met during her freshman year at Northwestern University. The relationship lasted about five months and ended when Lepore transferred to another college in North Carolina, the book and contemporary reporting suggest. Brown’s portrayal of Meghan’s dating life in those years depicts a pattern of brief partnerships, each described by associates as part of a broader drive toward professional opportunity. Other reported relationships include Shaun Zaken, a fellow actor she reportedly dated for several months in the early 2000s, followed by Brett Ryland, who would later work as a writer on a television show; both relationships are described in the biographical material as part of Meghan’s youthful exploration rather than long-term commitments.

Before meeting Harry, Meghan was linked to American film producer Trevor Engelson, whom she reportedly met in a bar when she was 23. The two wound up marrying in August 2011, a high-profile union that drew limited public attention in the context of their later divorce. Brown quotes a wedding guest who noted Meghan’s preference for a quiet approach to social media at the time, even as she was already gaining momentum from her role on Suits. The couple separated in 2013 and divorced the following year, with contemporaries describing Meghan as feeling that her professional ambitions outpaced her collaborations with Engelson. A later recounting by Brown describes Engelson as believing he had been used in the relationship, while Meghan was portrayed as pressing for greater advocacy on her behalf within the industry. After the split, Brown notes that Meghan sent a keepsake package by registered mail to Engelson containing her engagement ring and wedding band, a gesture that has been cited in discussions about their parting.

Meghan’s last relationship before Harry was with Canadian chef Cory Vitiello. The two reportedly dated for about two years following her divorce from Engelson, with Vitiello later saying he respected Meghan’s privacy and did not seek to portray himself as a central figure in her life after their breakup. He emphasized that he welcomed Meghan’s happiness and that he did not intend to insert himself into the narrative of her marriage to Harry. This phase is framed in Brown’s account as part of Meghan’s ongoing navigation of personal relationships while building a professional profile in the entertainment world.

As the narrative of Meghan’s dating life unfolds toward her future with Harry, the question of how much she knew about him before their first meeting remains contested in biographical circles. In Oprah Winfrey’s 2021 interview, Meghan suggested she did not extensively research what marrying into the royal family would entail, though Harry’s 2023 memoir Spare recounts another moment when he recalls Meghan not recognizing his uncle Prince Andrew. Biographers Carolyn Durand and Omid Scobie, writing in Finding Freedom, contend that both Meghan and Harry did their homework before their first date, noting a mutual interest in understanding one another in the run-up to the Dean Street Townhouse encounter in 2016. Vanity Fair has quoted commentators who argue Meghan’s tendency to research options—whether menus online or career opportunities—fits with this portrayal, suggesting she would likely have some awareness about the realm she was entering.

Friend Ninaki Kato, who described Meghan’s early fascination with the Royal Family, recalled Meghan’s love of Diana: Her True Story on her bookshelf and said Meghan was drawn to the idea of a royal life, citing her fondness for The Princess Diaries as a touchstone. Meghan herself later reflected in a 2014 post on her now-defunct lifestyle blog The Tig about dreaming of being a princess, framing the royal equation as part of a broader narrative about public aspiration. After stepping back from royal duties, Meghan and Harry have continued to expand their public footprint through a Netflix deal, a docuseries, a book, podcasts, and other projects, signaling a sustained effort to shape their image on their own terms. The two now reside in Montecito, California, where their public-facing ventures are linked to a broader brand strategy rather than a single roles in a traditional company or monarchy.

The reporting around Meghan’s pre-Harry dating life reflects a willingness among royal biographers and friends to map out the personal history that shaped her path to the royal marriage. Brown’s Palace Papers and related commentary emphasize a convergence of personal ambition and professional momentum that characterized Meghan’s twenties, a period defined by quick shifts in relationships rather than long, settled partnerships. The narrative continues to feed public interest in how Meghan’s experiences before she met Harry were interpreted by friends, family and biographers, and how those experiences—both real and mythologized—contributed to the perception of her as a public figure who has consistently shaped her own story.